Die, Workwear: "This is how to look better in your 20s and 30s"

Date
Duration
46 min
if you're a young man in your twenties and thirties and you want to be more confident this episode is for you and it's gonna be a little strange if you saw this headline if you saw this title you're gonna think why on earth this happening on a business podcast today's episode is with die work where die work where is the username of a person who's gone incredibly viral on twitter he has over a million followers and he talks about men's fashion i saw this guy pop up last year and it kinda changed my life because he taught me about dress and how dressing a certain way it gives a huge amount of confidence and the problem is that you don't try to dress nice because you don't really know the rules and so i thought it'd be fun to talk to derek about his rise so how we got huge and built the business but also some practical tips on how to dress better and what that means for your life and what that means for your confidence so give this episode to listen and i'll talk you in a little bit i feel like i could rude where i know i could be what i want to from at all in it like a days on on a roll i think the reason why you're blowing up right now i'll give you my opinion and maybe you could give me your opinion but i care how i look and i've always cared about that but i never really knew the rules and and basically when you don't know the rules of something you feel not confident and you kinda just revert back to like well i'm just gonna do the lazy thing of like wearing f leisure or like kind of boring clothes but you have this line that you repeat constantly which is clothing is a social language and you kinda have taught people how to speak it which kind of gives confidence and it makes your clothing feel like armor but also you're dressing like the person you want to be and you're speaking the language of the people who you wanna speak with and kind of what you wanna behave like and i think this is why millions of men have liked you because you're giving them confidence and teach of them the language i do think of clothing a social language and i've always thought of it in that sense because you know if you grew up anytime before the internet you know you may have been part of some social group around a hobby or an interest like you're a a skater or you're into punk music or whatever and everyone i knew dress a certain way to communicate identity like they were a jo or there a nerd or whatever and there was always rules around that look even if no one wrote a book and spelled it out for you you kind of knew that this was the look and everyone kind of conform to the look of their social group in identity and it kind of broadcasted a message and i think over time i've just kind of taken that idea and talked about how it's also used in class like tailoring or you know tech wear or whatever's is the aesthetic genre people are using dress to communicate something and even people who dress in ways that is subconscious that they they think they don't care about clothes they still kind of dress according to their social economic class i bring up this example often there was a moment in their tech industry in the early two thousands where the hoodies and jeans uniform was a way to signal i don't care about clothes i'm like the whiz kid you know kind of hacker that's reshaping the economy all i care is about merit talk and skills but it just so happens that over time within that industry everyone starts to also dress the same so to some degree people are at least conscious of what is the look within their group and they were careful to not deviate too far from it because they want to signal that they belong there's a there's a article that often mention on twitter and sometimes in interview the author's name is carlos but i can't remember his last name but he wrote an article called inside the merit mirror like looking into the mirror and tucker and and his article was about how even in the tech industry where people say they don't care about clothes everyone mirrors each other and clothes do play part because if you showed up to a job interview for the tech industry and you wore three piece suit people assume that you don't fit in and they will read something into your clothes to some degree clothes do matter this is the first time we've ever done an anonymous podcast and i wanna ask you bit about your ride so if there's ever anything that you just don't wanna answer to let me know but is this your full time gig now which is kind of being a a writer or whatever it is you describe yourself as yeah i make my living off writing about men mentor there's a this concept that i think i learned from you or a rabbit hole you set me down is it called where it's like you're being careless but it that's kind of the cool part right it's like not trying too hard but you look amazing did they explain that accurately yes it was originally introduced by an italian writer during right that's eighteenth seventeenth century and the writer who originally used this term was describing how to serve the king and they were saying that you should do things in a way that conceal your effort an easy way to understand this is like if sam asked me to do a favor can you you know pick up my car from this location and and drive it to this place i will do the favor but insist that it's no big deal it's not a problem don't worry about it even if it is actually kind of inconvenient and it's a way to essentially i guess serve you is to make the person feel good about what they've asked of you but sp in men's style sense is basically to dress in a way that conceal the effort that you've put in but the concept goes way back before this writer it goes back to even b who is largely understood to have shaped much of modern men's style and b will use to spend hours tying his cra his white cra which is kind of like a neck this a famous story probably made up but the the story is that one of his valet was seen exiting the room once with a huge pile of cra and someone asked him what what are those for and he said these are our failures and the idea was that bra will actually spent hours and hours and hours in the morning putting together look and then he'd walk out and the pretend that he just happened to have fell into these clothes like it was no big deal it was a complete natural thing he he woke up like this and that is part of the idea that style is kind of a natural extension of you it's not an art fist and that sort of you're doing sp with your twitter handle and with your writing and with your reach you're like oh i just kind of just wrote what came interesting and i don't know how big it is but in reality you're just behind the scenes just scheming you're just you you're like oh i just wrote this this really funny burn to this guy who replied and it just happened to get two million views because that's what one of your the things that you do which is pretty funny is you like reply to a couple people but you murder them like it's called murdered with words you just a kind of annihilate them and and that's kind of your your style which i find hilarious but one person you've turned me on to is ralph lauren and ralph lauren has an interesting story but i'm like getting obsessed with some of his quotes because he was raised a very normal background but he said that he got obsessed with movies at a young age he was like i i you know i'm not sure if i can be an actor but i can design my life via clothing you know if i put on a farmer's outfit i'll feel like a farmer if i put on a soldier style office i'm gonna feel like a soldier i'll feel tough and brave and he he has this great quote he says i don't design clothes i design dreams and then he dresses as as if whatever he wants to become he was a jewish kid from the bronx he was like i wanna feel like this like old money's sophistication so he started dressing like that and he became it and i think that's what is interesting about what you've opened up to a lot of people is this idea of like acting as if and then you become yeah if you go through a ralph one flagship it's not true for their normal stores their normal stores there's normal stores but if you visit a ralph lauren flagship it's like walking through like cut center like the amusement parks and there's like the pirate ship world and there's a rockets a ship world and all that you go through a ralph one flagship there's like the ranch world there's the old money world there's you know there's all these different worlds that he creates around costumes and it's because he knows how to view you with both that fantasy and to kind of use that language and design to reference different social ideas and identities i wanna ask you practical tips on like dress and things like that but i actually wanna ask you practical tips first on learning i've noticed that you're pretty insane like i i read a blog where it starts off like saying in the nineteen fifty nine book try for elegance which around men's clothing and then you like quote the book and you tell a story about the book and that leads into the rest of your writing i went and tried to find that book that was a book that's out of print that's like three hundred dollars or something like that and it has like no reviews on amazon and then you'll do like the history of tweed and i'm like how the hell you know this shit and so what i wanna know is how are you learning all these things in storing the knowledge that's what fa suit me about you is like your mastery of a topic that comes with a lot of buying stuff that ends up being crappy so i've bought a lot of books on clothing if they're you know especially old books and if it was published in some you know some time and it was this obscure book i'd buy and then read it and a lot of that stuff ends up being crappy but sometimes there's like a nugget over time i think you get a better sense of like which books to buy obviously you're not just constantly doing the scatter shot but i do end up buying a lot of books and then reading them and then sometimes there's like a nugget here and there it does help i would say that fashion as a topic for a while was not treated seriously and then to the degree it is treated seriously it's often focused on women's clothing and then to the degree that men's clothing is taken seriously there are many brilliant academic writers who focus on men's clothing but they tend to be extremely academic so i am in a space where i'm just ent and i tried to write something that ties clothing into other parts of culture which i hope makes it more interesting to everyday people and i i try to do something that's little smarter than just like basic trend reporting or fashion writing but it's a little bit more accessible than academic writing and then also tread this water where not a lot of people are tread and i think that kind of helps i think it helps to be in this very specific space today you had a thing about like the quarter zip and like that caused us so much so much outrage and i think i i said you're were coming on i got so many people that pissed off that you're coming because they're were like dude he he's so unrelated to the middle america guy and i think though that oddly those people are folks that are being turned onto to you right now what are the the common issues that they come to with and what's the general advice so the three most common things for like if you do this this and this you're gonna be sixty percent of the way there or significantly better you can't answer any of those things without first thinking of close a social language and the thinking of what you wanna communicate so if you think of close a social language you are to me like ninety percent of the way there because then you can think of like how something should fit and the colors and the styles and all that to combine i admit that as my account has grown i've leaned a little bit more towards tailoring before my account started grow i talked about a much wider range of styles often like japanese work wear or something and i've i've leaned a little bit more into tailoring because that's an aesthetic language that i think more people understand is that limited as suits suits sport codes anything that would be concerned like maybe smart casual i think there are certain kind of aesthetics that like everyone recognizes oh that that's good again bringing it back to language if you think of like dialects receive pronunciation everyone recognizes that as like the quote unquote correct pronunciation and they recognize recognized as the good english but you know throughout the uk there are many dialects and even though everyone recognizes received pronunciation as the dialect if you speak receive pronunciation in certain parts of england you might come off as kind of crazy because everyone there speaks in a different dialect but if you take that dialect and put it across the nation a lot of people are gonna be very opinionated on whether or not that is the correct way of speaking because that's very regional so there are certain modes of communication that are he harmonic and suit sport coats a certain kind of like dress kind of look is what i would consider he harmonic in visual aesthetics even though wearing a tour coat or wearing a punk rock biker jacket or other aesthetics can be legitimate in their own way it's just that if you present that to other people it's more controversial and a fewer people are going to recognize it as quote unquote good because it's so regional the problem with i i admit when you're talking about like the midwestern guy i get this a lot is that somebody from outside of san francisco or in new york city or los angeles to say i really like what you put out there how can i dress like this and that is sometimes a question i can't answer because if you want to wear sport coats and you live outside of of handful of cities and especially if you're fall outside of you know straight sizing let's say you're a size forty six chest i just got an email the other day someone has a forty eight chest but a thirty two ways to they're a professional baseball player if you're that build and you are outside of the major cities i don't really have an answer for you because tailoring has died over the last few decades there aren't many good tailor so what you're going to find is a lot of ready to wear tailoring which is not gonna fit an unusual build and then you also have to be the kind of guy that's willing to wear a sport coat even though other people aren't wearing a sport coat you have to put up with the fact that you are over dressed and you're doing it for yourself and it's pleasing to you so sometimes if you're in a smaller city there may not be a lot of options and there may be i think harsh judgments whereas i think in a big city you have the certain kind of immunity where you can address very different from others and nobody cares like nobody cares if you arrive to the office in a sport code and everyone's dressed down i still think you can in a small city i have a friend who works for a religious organization he lives just outside of nashville yeah men mu men gentlemen music men's were mu matt mitchell yeah he works for a religious organization and he wears sport coat with jeans to the office he told me that nobody in his office wears his taylor clothing up for the really old guys but he does it so often now that that's just like him and one he's obviously not gonna get fired for it but two it's not like anyone comments on it hey more is just him and i think it does take that kind of personality and it takes a willingness to really hunt for those rated wear pieces to figure out how things fit because historically men dressed well in tailored clothing not because they knew all of the stuff it's because they went to a local cloth and that cloth you're like outfit outfitted them they you know you you go to your cloth and you'd say i have to go to summer wedding or i work in this office like just figure out how am i supposed to address and that cloth you're told you you're going to some wording this is the thing that you're supposed to wear and they'd figure out how it's supposed to fit and they do all the tailoring and all that and you walk out and you look amazing those clothes have disappeared and customer loyalty is no longer there as well so whereas a man used to go to his tailor and would introduce his son to his taylor now men shot from different places not only different aesthetics but they might buy their jeans from a gene company shirts from a shirt company socks from sock company sometimes they're also buying the stuff online where there's no sales associate to guide them and then they have to figure out how to put together not only a good outfit but also a good wardrobe and how to use that wardrobe to move throughout different social spaces alright you're just telling me this and i'm like alright i'm bought in all that but i feel hopeless so i live right outside new york city so it's okay for me i can go to new york city but i still feel hopeless for i'm like this sounds super intimidating finding it taylor yeah there are solutions depending everyone has to figure out their own specific situation if you're the guy that emailed me recently he's a baseball player forty eight chest thirty two waist you are absolutely not going to find anything and ready to wear or made to measure you have to go to bespoke most people are not that build most people are not professional baseball players most people are actually pretty average size so they can usually get a good enough fit and ready to wear i have some articles on you know where i think you can shop for a suit but the issue is still that the effort is put on you you have to figure out what are your fit issues how do you wanna address how to put together a wardrobe someone recently emailed me with photos of a poet this person's writing an article about this poet life and this poet lived somewhere on the east coast early in this poet life there was photos of him as a young person i would say like in his twenties or so in the nineteen thirties and then over time you see him in in the in the twenties and thirties he dressed really really well exceptionally well i mean average for the time but looking back like very very well yeah and then over time his dress started to worsen and as i was explaining to this writer if you can imagine this poet has an interest level in clothing loop will say seventy out of a hundred in the nineteen twenties and thirties he just has to walk down the block to get whatever he needs and then over time as tailoring disappears it's harder to find good cloth and the the number of options balloons and there's all these different languages a level seventy is only going to get you so far your interest level has to be ninety or ninety five to get to how he dressed in the twenties and thirties because now you have to source things online and you have to do all this crazy work there's a lot of burden now on on the consumer which is partly why it's difficult to build a wardrobe it doesn't mean that another a podcast interview interviewed me once in and they asked do you feel that most people are badly dressed and it that's a very loaded question because i think there are many well dressed people if you understand their own dress aesthetic language when i walk around san francisco i see people wearing cool hiking gear or vintage gear but they're often like embedded in some kind of cultural community but if you're outside of a cultural community that doesn't have much cultural capital because that's in my view how we think of aesthetics we think of in terms of cultural capital and social language if you're outside of those communities and you're not a punk and you're not a cool hike or you're not part of a rock band or whatever then you kinda have to figure out where to buy the clothes express an identity that you like and how it should fit and all of that and yeah it's unfortunately a much harder a uphill battle than it was fifty years ago there's a really good he used to teach business at university of california berkeley i don't know if he still does his name is barry schwartz and he wrote a book called the paradox of choice that book opens with a story of how schwartz enters the gap and is shopping for a pair of jeans and the sales associate asked him do you want washed raw rinsed white dark blue slim fit straight slim straight tapered you know baggy athletic cut and he gave him all these options and he said he walked out that day from the gap with the best pair of jeans he's ever bought but he was left more unsatisfied than he's ever felt because just knowing that there are so many choices made him question the choice that he made that day and part of his book is that people are often better off if they're given a much more constrained number of choices so if you think of like going into an apple store there are very few choices and they've constrained it to make the purchasing decision process easier but they are i mean presumably they think so they're all good choices and the problem at the moment at the market is that there are billions of choices for any style of item following any number of design languages any number of fits and that hasn't caused incredible anxiety in the market which is very difficult to solve here's how i'm solving it is as i go to your blog or people who i like or follow on instagram and i'm just like i'm just gonna do what they do and and and it's sort of like when you learn how to play music you play other peep you you play other people's music for a long time and then you start feeling like man i love like this little r from this rock like genre and then i i like i'm inspired a little bit by this thing and i start crafting my own because i've just learned the technique and i know like what's cool and what's not and what's my texture dress it's kind of the same thing where it's like alright i'm new so whatever derek whoever i follow on instagram does i'm just gonna copy that and in doing that after a couple years i'm going to develop my own sense and then so like the question i have for you which is it's hard to know when you're shopping online which is what i think most people in their twenty and thirties do it's hard to know what's good and the reason why you need to know what's good is because if i were to follow what you and a lot of people say i would be buying so much stuff but that's not exactly what you're wanting me to do i think what you and and and what i believe is that you should buy for life you buy less things but you buy high quality things that can last a lifetime i still struggle to figure out what those high quality things are and so my question is how should i figure out what is a high quality brand or high quality product that is deserving of more money to be spent online yeah all i agree with everything you said of of find people that you like can copy them on the issue of how to find the quality thing so there there are it sounds like you've read a lot of my work so i've written about different ideas of how we think of quality there's the build quality so there is such a thing as as a certain kind of build quality with clothes so to give an example leather dress shoes if you buy leather dress shoes made with a blake stitch or goodyear we on the sole and the upper are made from full green leather those shoes will age better last longer and they can be res sold like like an all then yeah like an all in versus if you buy something with a glued on sole and made from corrected green leather that corrected green leather is a bad leather that's been sanded down to remove the blemishes or scars and whatnot and then coated with some chemical to make it look smooth and normal again uniform and that coating eventually flakes off doesn't age very well so you end up looking at your shoes and you don't like how they look and then you go out and buy a new pair whereas full green leather will age better over time it will look more natural it gets the kind of pat that people like and then with a stitched un sole you can always un stitch the sole and replace it you can actually still replace glued on souls but it's a little bit more risky there's only so many times you can do it and i wrote an article and put this on how to judge quality clothing and it runs through almost all of the categories i mean you know except except for like gore park i mean generally speaking sweaters choose tailored jackets you know like woven shirts things like that like how to think of quality but the scope of build quality is actually pretty narrow you there are some things that are generally agreed upon as what is good build quality to give an example with taylor jackets there are certain kind of ideas of what is a better or worse taylor jack in terms of build quality but some things are pretty subjective and if a designer is trying to bring a suit or sport coat to market they're working with a factory and that factory has let's say like three hundred operations there is a certain gold standard for quality quote unquote but a designers is often not trying to sell like a five six seven thousand dollar suit they're trying to sell a two thousand dollar suit so they have to make design decisions on where to cut back quote unquote and how they decide which part of those three hundred operations to cut back is more is i think very subjective but the real measure of quality should be are you excited to put it on today and do you think you'll be excited to put this on ten years from now that doesn't always mean wearing in a class aesthetic it could be me mean wearing something crazy because you like wearing crazy clothes and then will this thing last to you know some degree there is there is like a certain kind of build quality in terms of wool this thing last if you buy something and it falls apart in two years i think most people would want something that lasts a little bit longer than that like as a physical item so i think those things do you get side wearing it will it last design wise and also kind of construction wise and then also does it fit and flatter you when you put it on and you look at yourself in the mirror do you like how you look and i think those basic points are you excited by the thing that you're wearing and does it fit and flatter you i think gets you much further than thinking of this purely as an engineering problem you can't just read specs off a sheet like when you're buying electronics to some degree it's more like food when you bite into it does it taste good are you decided to go out to that restaurant i think that's a much more a better way to approach things it's a more holistic way to approach things than thinking of it just in terms of is this well made when i was kinda up and coming in my career i didn't have a lot of money and you know i started my own business and like didn't pay myself very much and so i was like afraid to to spend and buy things even though i like wanted stuff you know i was but even after i made a little bit of money i was still always nervous to spend and so i see guys like you you know these writers who who i admire and they've got like some great clothing and in my head i'm wondering how many items do they actually own in their closet and how many like because like up until recently i could have gone six months without buying a clothing item now i'm like you know i think on your blog you say when you first get into this shit even if you have money buy slow ease into a little bit and i'm like holding myself back because i'm like oh i wanna get this and i afford it so i'm like i want all this shit how many things do you buy per month and what's like a reasonable amount of spend do you think for someone who can can can afford these things well i do spend a lot more than the average person i admit that i don't know the exact number but to give an example i recently bought a hoodie from bare knuckles i bought two double l flannel shirts double flannel shirt is what two to four hundred no no no i wouldn't i would never have bought of four hundred dollar flannel shirt i think i spent i wanna say like one seventy five i bought a pair of bryson cargo pants those were kind of expensive are like three fifty but i've been lust over them for like a year so i finally just bought them that's for this season i don't really imagine myself buying much for the rest of the season so you know i think most people are not buying too shirts a hoodie in a pair of pants twice a year because i i break up my shopping into seasons springs summer fall winter and then i do use a lot of custom tailor and i usually have like a pseudo sport coat in the works through a custom tailor and that's been true for a while so you know again that most people are not doing that those suits are getting tailored are those bespoke or those off the rack that you're getting fitted to you oh they bespoke that's interesting that has always intimidated me because it seems like it's a it's a pain in the ass of a process and according to your you have one post in your blog you're not sure if you could even tell the difference all the time yes i had this friendly argument with a good friend of mine who strongly feels that you can tell i will say i was in a dm i am i am in a dm with some guys who are into clothing and we were looking at a politicians suit and we all suspect that he's wearing bespoke because of the stitching and the styling and all that and we can and we can kind of pinpoint the region of where the taylor from but potentially the this person's is wearing like five thousand dollar suits is what you're saying no i would i would estimate that their suit probably cost around three to four thousand okay and then i checked their twitter account and they follow me so i was like maybe they do buy suits so maybe you can tell but i i'm still very skeptical of whether or not generally speaking you can tell the difference between bread wear bespoke and i completely agree i think bespoke is a huge hassle there's more misses than people let on online i think it's very important when you go into that space to know that like not all commissions turn out well and it's after pretty common that commissions turn out poorly even if you're using a good tailor but there are a lot of bad tailor one there are some people who need bespoke we have to define it is the terminology like off the rack and then one up from that is like made to measure which is i guess a suit supply and then is bespoke purely from scratch well the short answer then is ready to wear is what you go into store and can touch and feel and put on yourself and put back on the rack made to measure is something that has a block pattern which is a pre made pattern that they adjust given your measurements you're measured and then they adjust the pattern make the garment straight to finish and then you come in for what they call one fitting which means they they put the garment on you and they figure out you know what needs to be changed that fitting is basically not that much different than putting on a ready wear garment and they do adjustments the only sometimes difference is that in a mate magic garment they they have more inlay which means there's more room for adjustment and in bespoke theoretically is that the pattern is produced from scratch and then there's a series of fittings typically three base forward and final fitting and then it's sort of like you can imagine it as someone sketching like when you're you know when i was in art class in high school they taught us like do a sketch and then you kinda like fill it in and then you kinda of work it out a fitting is sort of like that the tailored sketches out what they think is gonna look good and then there's a fitting and figure out what adjustments needs to be made and then through that iterative process supposedly you wind up with a better garment reality is a little bit more complex than that but that is that's the general contours but your recommendation is for most people is it ready to wear and that you get tailored absolutely ready to wear because few reasons one is that most people are straight sized meaning they can fit into a radio garment because those garments are made for the average sized person and then two the tiny differences you're probably not as obsessed as i am with like oh like the quarters are not open enough and like the shoulders you know you prob you probably are not like obsessed over those things even if you are obsessed with those things you have to like realize that like ninety nine percent of people seeing you not gonna see those things and even if they do see those things you have to be standing like a robot for someone to spot those things in real life you move around and you're sitting and you're interacting with the world so like all of the things that people are talking about including me those disappear and then the third thing is that most people don't care about the craft element and even if they do think they care about the craft element they probably came and spot it so like can you tell a difference between a machine butt hole and a handmade button hole no of course not a very few people can i think yeah so like there are some people who need bespoke and those are people like john fed will never be able to fit into an off the rack garment or even made to measure because he's very far from the average sized person he would have to go bespoke if he wanted to suit that fit but most people are not that person and the most important reason the the top tier reason of why everyone should try ready over ready to wear first is because you can try on the garments and put it back on the route nothing happens at the end of the day whereas with a custom garment if the tailor offers you a money back guarantee they're not a good tailor no good tailor will ever offer that because it takes a lot of time effort and money to produce a good suit and then if there if it's final sale that means that if you put it on it might not fit well there's no guarantee that's gonna fit well but even if it does fit well you might not like the silhouette you might have chosen a crappy fabric maybe you asked for dumb details and then also of the garment produced you look at and you realize oh this actually looks horrible there are many things that can go wrong and then at that point you've just spent anywhere from you know like two to eight thousand dollars possibly for a garment and you can't return it whereas with the ready work garment you can try on a ten thousand i i don't even know if twenty thousand dollar suits exist rip for ready to wear but if they did you could try it on and put it back on the rack nothing happens and that's the number one reason even if you are just getting into this and you suspect that you need a custom garment i still think you should try ready to wear it because when you try ready to wear you can start to identify certain things you can start to say oh actually don't like how i look in a in a very soft shoulder jacket i think i need more padding or i don't actually like how i look in a three button jacket i think i want a two button jacket and once you start getting an eye for that silhouette you can then start to find a tailor because if you know that you want a very padded cut that narrows your options i have a tailor now and i don't know if i like like it's kinda funny first of all a lot of tailor is it a red flag if your tailored dresses poorly or has poorly fitting close or is it like one of those things where it's like the cobb kids is the last kids to get shoes you what i mean yeah it's cobb cases last there are many tailor who who also dress probably because for many tailor are better thought of as technicians they're not like stylist so they themselves are often just wearing something that's not very interesting so i i wouldn't judge a tailor work by how they dress but i would judge a tailor work by the customers that come out so if the customers come out and they all are wearing suits that don't fit the chance of you getting a good suit from that taylor is very low but if all the customers walk out and their suits fit perfectly and especially helps if the customers walk out or have a similar build as you so if you are a very heavy guy and you see heavy guys walking out store and they all have suits that fit beautifully both then yeah the chance of you getting a good seat from that tail is very high obviously you're not gonna stake out a taylor shop and like just you know like walk see comes out the tour but you can do this on instagram you can go to instagram go to the tags sec section and you know see if the people that wear their clothes if they're clothes fit will yeah i am i like to collect old denim so i was i've been into salvage and rod denim since probably two thousand eight like it's kind of a weird hobby so you are not new to this if you if you're into denim in two thousand and eight you are actually you're very seasoned and so you know this stuff very well i'd denim is my pet i'm i'm i'm a an american history nerd i'm very passionate so have you ever seen a tv show american picker yeah i used to work with mike when i was in college that was my college job was working with mike from a picker and so i i got i'm and i'm obsessed with american history and there two two or three things that are very american art denim and the leather jacket and so i've always own shot leather jackets or i've always put or bo leather jackets yeah and then like red tag levi's or big e levi's i was one of the worst cover customers of i'm willie and i would spend like un godly amounts on denim and i would say i have them all saved i've dozens of them saved because i wanna i i read he and i've like been the fate of the paid friday like i you were you were presenting yourself as new to this hobby you are as seasoned as to come anyone who says all of those words he and i willie and you know shot well mad carry from my machine like i used to go to the store all the time when i didn't have any money and they would kinda pity me and and give me a shirt every once while and then like when i started making like in ten dollars an hour somewhere i would like i bought my first eye jean and i would get shrink to fit levi's back when i was eighteen i i loved that shit but as i got bigger i i got i'm a weight so my legs got too big for a lot of these like traditional stuff so i've i've been i used to go to self edge and s f and get yeah flat that was got anyway the japanese shit i love and so my point being i spend all this money on denim and what i've and and it's sort of like you start as a beginner where you buy cheap shit and then you go in the middle which you buy really expensive high end stuff and then now i've sort of ended on the other side to where i'm just buying thirty dollar wrangler that fit well and so but like with with with tailoring stuff that that's what you've inspired me with is tailoring stuff i'm kind of new to where i'm buying the cheap shit thrift stuff that that i could taylor that's actually pretty dope but then i'm like going to like suits supply which is like the thousand dollar shit and i'm like it kinda fucking sucks like i should either like go to like keep the cheap dude cheap thrift stuff that you get tailor or go like pretty high end that journey what you're talking about imagine if you started that denim journey and you're buying like twenty one ounce iron hearts yeah you would probably not even get into it because you would be like no insane buy yeah yeah the only way that you end up buying twenty once out ounce iron denim is if you start with fourteen and you like how they feel and then someone says oh why don't you try sixteen ounce and then you you like we you really like how i feel and then you move up and also you're at twenty one ounce and then you like i actually do like this even though it's no sane person would like this but it's just because i'm in this hobby i'd so that's to me the same with rated wear with tailoring is that you start you have to figure out what you like there's a really good book there like it's called perfume the guide by luca tu and tonya sanchez a book on perfume yeah but it's just it's just a it's just a list of reviews so it's helpful if you if if you're into perfume and you wanna look up a review of with someone thinks of a perfume but in the introductory chapters tanya sanchez rights i've talked to hundreds of people are into perfume and they all seem to follow a similar journey in the beginning there's this exploration stage where you're like finding perfume and like your mother's wardrobe or your father's dresser or whatever and then you explore different notes and then there's the stage where you think you've found your taste and you have very rigid rules about everything you very strong opinions and then the third final step is what she feels is nirvana where you know the rules but you're not like strict about them and you just like what you like so i think that's actually pretty true for a lot of things whether you're into motorcycles or whether you're into you know your foodie or you're into fountain pens is that people start with an exploration stage they figure out the terrain you know the hills are over there and the lakes are over there and then they get very adamant about rules like everything has to be this way and then there's a point where they just know what they like and they're not as adam about the rules and sometimes the things that they like are not even the expensive coveted things that everyone talks about it's just something they like and that's it that's the that's the emotional that's the nirvana that you reach so the thing that you like might just be wrangler it's just a pain in the ass that you have to spend as much money that much money and in a decade to go through this and and that's why i mean that's why i like reading your blog and reading people like you is like i'm like how can i just like speed some of these learnings and just not make the mistakes that i've made before like for example a big thing in clothing that the that a lot of people are bringing back is high rise trousers and like yeah there was this period where we went through like slim clothing and first of all it's the fucking worst because it looks stupid looking back on it and it's like incredibly uncomfortable and like half the do half of men can't like they got big ass as a big dots it's like we can't wear that stuff like you could you can only wear that stuff if you're a smaller person but it's like i just wish i would have like stuck to more timeless things and thought what will what was cool fifty years ago and will likely be cool in fifty years from now or what i think will be cool and i just wish i wouldn't to have gone through that that that slim phase because now i have so much slim stuff and i've spent tens to thousands of dollars probably on it yeah i mean i will say that that high rise fuller like look i often talk about online in the context of tailored clothing if you're if you wanna dress like mick ja and rock and roll kind of like you know tight leather jackets and tight rock t shirts then you need tight pants that only works if you're a small if you're a small a smaller person by the way it that yeah i don't think like you have to be a very thing dude if you're above five ten and over like one eighty it's hard to pull that off because you just looks like you look stupid and i've tried to do that and and i look so dumb i i do think it helps to be a certain build for that look and then the whole look has to come together you have to again think of it in terms of like a social language thing but if you're wearing a tailored jacket like a suit jacket or a sport coat i do think there are certain proportions for the trousers that work better for the jacket and especially is is works better across a wider range of men there are some men who can wear very very skin tight suits but they are often very thin and they usually have very broad shoulders compared to the waist they're basically models like if you look at runway models they're wearing those suits they do look good but most people are not built like that and a jacket can only be as tight as your body allows so at some point you have to figure out how to create a trouser silhouette that works with the jacket that you're wearing and the jacket is constrained by your own body's proportions i appreciate you coming on this podcast you're the man and thank you for everything thank you thanks for having me on this was such such a pleasure to be on so thank you for the opportunity thank you and that's the pod i feel like i could rude world i know i could be what i want to put at all in it like a days off on a goal travel never looking back

Episode Notes

Episode 649: Sam Parr ( https://x.com/theSamParr ) talks to Derek Guy ( https://x.com/dieworkwear ) about how to dress better, have more confidence, and where and how to build a wardrobe that lasts decades. 

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Show Notes: 

(0:00) Why it matters

(3:17) Sprezzatura

(6:01) Ralph Lauren

(9:33) Advice for the American male

(15:16) How to find a tailor

(17:21) Why we dress worse now

(20:15) How to build a wardrobe

(24:54) Budgeting

(28:23) Ready-to-wear, made-to-measure, and bespoke

(34:21) Personal style nirvana

(39:18) Buying for the decade


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Links:

• Die, Workwear! - https://dieworkwear.com/ 

• Inside the Mirrortocracy - https://carlos.bueno.org/2014/06/mirrortocracy.html 

• The Paradox of Choice - https://www.amazon.com/Paradox-Choice-Why-More-Less/dp/0060005696 

• How to Judge Quality in Clothing - https://www.putthison.com/how-to-judge-quality-in-clothing/ 


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Check Out Shaan's Stuff:

Need to hire? You should use the same service Shaan uses to hire developers, designers, & Virtual Assistants → it’s called Shepherd (tell ‘em Shaan sent you): https://bit.ly/SupportShepherd


—

Check Out Sam's Stuff:

• Hampton - https://www.joinhampton.com/

• Ideation Bootcamp - https://www.ideationbootcamp.co/

• Copy That - https://copythat.com

• Hampton Wealth Survey - https://joinhampton.com/wealth

• Sam’s List - http://samslist.co/


My First Million is a HubSpot Original Podcast // Brought to you by The HubSpot Podcast Network // Production by Arie Desormeaux // Editing by Ezra Bakker Trupiano


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