Silicon Valley Fashion With The Menswear Guy

executive Jensen Wang and his wonderful swag. He this man knows how to dress, which can be rare in the tech industry. But I've brought in mementswear expert Derek Guy to discuss it. Derek, thank you so much for joining me.

I think he's very stylish, But he kind of dresses a bit like an evil character because he does these kind of all black outfits with these most of them look like to be cowhide or look like cowhide, possibly go hide leather jackets, sometimes exotic leather jackets. But it's always this kind of very sleek, all black look that you know, you generally kind of associate with kind of ominous evilness.

And his jackets fit very well in that Essentially he gets a very nice kind of upside down vs for the zippers, which demonstrates that the shoulders fit well, and the cut is done intentionally to create that kind of a little bit more angular look. Some of his jackets, I believe from memory, have what's called a long front balance.

So when you're looking at a jacket from the side, it's always fine for the front ham the front of the hem to be lower or even with the back, but you never want the front of the jacket to be higher than the back. Generally speaking, I actually can't think of many exceptions to this rule. But his jackets are cut such that he gets very very on some of the jackets, not all of them. On some of the jackets he gets very low front balance, and it looks very stylish that way. It's just a little bit

more of a stylized look. It's clearly I think he hired somebody to style him. His suits generally also fit very well, and my guess is that he just doesn't want to deal with different combination of outfits all the time, and this allows him to stick with a singular look and look pretty good in public life.

to be associated with the establishment. So after the Second World War, slowly people started to shed the suit and started to take on different types of casual, often casual that represented the working class. But I think there was a major shift starting in the nineties after the tech boom and the rise of Silicon Valley kind of billionaires. Essentially, it wasn't just that the suit was no longer desirable.

It's that another form of fashion became very desirable, and that fashion was the kind of like hoodie gens uniform that Mark Zuckerberg specifically ushered in. And it was desirable in the sense that it signaled a certain kind of new meritocracy to say that we don't que to the kind of traditionalism of industries back East. We're in California, shaking up the economy, and the only thing that matters is your skills. You know. SBF basically adopted this kind

of ethos. He looked pretty, you know, he dressed he did not dress very well, And I think part of that was this act to say, I am so in the world of intellectual thought and coding, and I only care about meritocracy that I can't spare a single thought to how I dress. But in reality, this uniform, this hoodie and Jean's uniform, especially in the tech industry, became its own kind of norm, such that it wasn't just

that people didn't care about fashion. It's that dressing a certain way signal that you were part of the group, part of the crowd. And now we see that the original people who ushered in that ethos are actually taking I don't want to say, you know, they're not. Mark Zuckerberg is not transforming his look, but at least since the fall of last year, he certainly has taken a slightly larger in and his luck, and he's transforming his

look a little bit. He's looking a little bit more stylish, and I think that that signals a naturally significant change in how the tech industry thinks about fashion, and then also how that is impacting the larger cultural space.

performative the I'm not really trying look is. But it seems like he's trying now, and I wonder if that is trying to sigle a shift in the industry at least with him.

dollars on T shirts. That was published again somewhere, and I want to say it was maybe the cut, but afterwards Mark Coodie's I'm sorry, Mark Coody. Mark Zuckerberg's team reached out to the writer to clarify to say that he does not, in fact buy all of his hoodies from books Bashford, and that he did buy one once but then just never did again, but he listed the names of where he gets his clothing, and they were pretty kind of I would say, in the know brands,

not super fashionable, but relatively in the know. So he named Todd Snyder, Buck Mason, John Elliott, which is very in the know. I think some other brands that escape escape me at the moment, but these these brands essentially are very rarely sold in just one store, So I thought he was working with a stylist. His team denies that he works with a stylist, but the difference of his clothes is that they are a little bit more

in conversation with what's trending at the moment. So if you actually go to his Instagram page, I think his Instagram handle is Zuck, you'll see that starting in I will say, like October or November of last year, his wardrobe dramatically changed. So before he wore pretty kind of standard T shirts, jeans, sometimes a sweatshirt, and the cut was pretty basic. The shoulders seems sat on his shoulder bone, you know, like slim straight jeans. It's so very very

basic kind of look. But then starting in October and November, you start to see the cuts change. He wore a drop shoulder scene. When he wore long sleeves, the sleeves would kind of stack a little bit around his wrist. What else was he wearing? He was obviously he adopted a gold chain, which was recently written about, I think in the Wall Street Journal and even Slate, And I think it just demonstrates a little bit more attention paid

to the idea of a silhouette. And yeah, I think he looks better for it.

Silhouette is the idea that if you take away all of the details in the outfit and you were just to think of the outfit in terms of shapes. Think of it as an outline that is basically the silhouette of the garment. So in that sense, sometimes you know, when people see like pants that are very crop they say, oh, well, those don't fit. Not necessarily. Sometimes pants are designed to be very cropped, and that's part of the silhouette. Sometimes sleeves are meant to stack around the on the wrist.

you move your arms, the cuffs would ride up on you. However, some designers such as John Elliott I'm trying to think of some other bahrain as another designer that does this, probably rick Ohens assume because he does these very long drap silhouettes. The sleeve is so long that essentially you get a lot of stacking. The material ends up stacking around your wrist and it's just part of the look.

It doesn't have to be that close fit. Only in one singular way, silhoette allows you to think of an outfit in terms of shapes and take a little bit more creativity.

regular guy thing. I'm focused on my merit. I also feel like, especially in such a male dominated culture and especially now in the Valley, there's a lot of this masculine kind of Oh, you want to be a big, tough guy, and fashion is not for tough guys, and I feel like it deprives them of something, It deprives them as something they could really enjoy, Like, there are so many parts of the Valley that enjoy I don't know, building composable software, putting together different pieces to make the

architecture work. Yeah, the idea of doing so esthetically is somehow feminine. It just feels like a loss for them.

nicer to eat a tasty meal versus boiled potatoes. And I think it's nicer to wear something that makes me feel good versus something that makes me feel bad, something that makes me feel happy versus something that adds nothing to my life. And buying those items, you know, if you're like really deep into it, like it's you know, like basically a core part of my life, then certainly can take a lot of time. But it doesn't have

to take a lot of your time. And if you just buy things that you like and make you happy. I think that just adds something to the beginning of your day.

what you did there. It isn't about necessarily putting a ton of attention in, it's feeling good about what you're wearing. The only time I've really thought of this happening in the valley at scale. Are you familiar with American giant hoodies. Yeah, So there was this weird, long period like a year or two when everyone wanted one. They were like actually quite hard to get there with these very heavy hoodies. And that was the only time I think there's been

like a known aesthetic discussion in the valley. And it's so it's something I think everyone could enjoy.

it just like it's just like cooking. You know, you could eat boiled potatoes, but you know you could also throw some seasoning in and it will taste better.

it's sort of like how received pronunciation. Even if you dislike the hegemonic kind of role that it plays, everyone recognizes that, like, oh yeah, that's like the hegemonic you know, way of speaking, and it sounds good. Once you break out of whatever is hegemonic, then you get into all these niche territories and there are gonna be a lot of people that don't like how something sounds or how something looks. And that's the same with you know, pronunciations

of regional kind of dialects. So when I think of hoodies, I personally like when a hoodie leans into a very classic workwhere look, so that's like raw denim jeans, olive fatigues, if you're wearing chinos, then I think it's better if it's if it's the kind of like tougher, more rugged chino styled after the mid nineteenth century Army chinos that were issued to US vets, versus the very kind of

like business casual look. And then you know, like service boots, blundstones for a jacket if it's if the weather allows you to wear both a hoodie and a jacket, then trucker jackets, bombers, chortcoats, like anything that seems rugged. Double

knee car heartpants also go really well with hoodies. But again recognizing that once you leave the world of hegemonic aesthetics and culture and all these representations, there are a lot of people who say, oh, well, you know that there's a lot of judgments about someone's class and respectability based on whether or not they are conforming to these notions, which I don't adhere to. But I think aesthetically that kind of like rugged working class look with a hoodie looks.

They're a little bit baggier. They don't have like you know, it's fine for a leather jacket to be baggy, but his does not look bagging in an intentional, thoughtful way. It's just kind of like a limp limp jacket that hangs on him. And then when you look at Jensen Wong, there are very strong angular lines that just make him look better for lack of a better word. And yeah, I think Jensen just happens. I assume because of his

immense wealth. I assume he just you know, hired a stylist to help him with this part of his life. When you look at early photos of him, he dressed as a typical kind of tech nerd, like polo shirts, Gino's jeans. It just didn't look very stylish. But in this way he looks great. I will say that there was a moment, maybe like ten years ago instill somewhat today, where you saw a woman in professional spaces ditching Taylor jackets meaning sport codes toit jackets, blazers and the like,

and substituting them for black double riders. And this was right around the time that black double riders started to become a fashion trend.

tight on the body. And then the double rider is is what you think of when you think of Marlon Brando and the Wild One, think of shot perfectos and as an asymmetrical zip, and usually a deep pocket on one side has lapels. And I would say, like in twenty fourteen twenty fifteen, when Eddie Slamaine was appointed creative director at Saint Laurent's, he and Kanye actually popularized the

black double writer as a fashion piece. And they made it from being strictly a utilitarian motorcycle garment and turned to fashion piece by kind of making them out of softer lambskin leathers, so that was kind of clear that the person was wearing it for stala and not for just like utilitarian purposes. And it was popular among fashion conscious men, but it was especially popular among women who are seeking an alternative to a tailor jacket.

doing television interviews. I think AOC may have even warned a double rider into congress and it was considered a form of professional dress. And I think it's interesting when I see Jensen wearing a leather jacket in this manner, that communicates not It doesn't communicate dangerous rebel. It communicates professionalism, put togetherness. I think it's interesting that comes after that kind of moment where women made it somewhat normal in professional spaces.

can see many of his looks there. His looks are a lot more They're less edgy, a little bit more kind of I don't want to call them basic, but they are. I think they're more approachable for many guys. Instead of like a basic button up shirt, he'll wear a camp collar instead of like the pollos that you see at Lacoste. He wears Polos with a skipper collar, which is I think a little bit more of a

stylish collar. He often layers with the jacket. He also, like Mark Zuckerberg, wears a gold chain and all of these kind of touches I think make him look a little bit better than most tech figures.

it as just a random creative expression. So you know Jensen Huong, for example, we've been talking about him during this podcast, whereas you know these black biker style leather jackets, black t shirt and black jeans, often black boots, So it would be it would ruin the look if all of a sudden he tied like a colorful I don't know, a colorful neck tie around his belt loops, you know, like that would just be right look, It would ruin

the look. I would say for many guys, start thinking about fashion and social language in that sense, think of the different kind of forms of forms that that language can take. So you know, you have to find an aesthetic that speaks to you that could be like punk, skate, work wear, prep, whatever, haven't guard, whatever it may be, and then dress with that type of intentionality. Dress with

that aesthetic in mind. Don't be afraid of I think when guys are shopping for a jacket, they they go wrong when they shop for the blandest form of a jacket, And what they should do is just think of the look that they want to create. And find the jacket that communicates that look. So it's it's more about thinking of an outfit the way that you would think about how to write a sentence, and less about like throwing

paint on canvas, for example. Think of the sentence that you want to write, and then find ways to buy clothes and create outfits that essentially communicate something as a sentence would.

you can do it with very lightweight layers. So in the summertime, or if you happen to live in a climate that's very warm, you can do a layering piece just by wearing T shirts and then layering a short sleeve, open kind of shirt. Or it could be a shambray shirt like a work shirt. You could even do a kind of like reverse layer. So for example, if you imagine a Western denim button up shirt and a pair

of jeans, that looks fine. But then if you want to create a more layered look unbuttoned, a few buttons on the Western button up shirt they're in a rib tank and then possibly even a gold chain and that will look better. I think when you create these layers,

create a little bit more visual interest that helps. Instead of wearing you know, Plaine Smooth Merino v Next and Crew Next sweaters that you find at the mall, get a textured sweater, so like a rib sweater or a Shetland sweater or anything with a bit of texture on it. When you again going back to Adam Mosteria, when you go to Instagram and you look at sweaters, they're often

they often have a bit of texture. Anything to add those elements, a bit of texturing, a bit of layering, I think will help an outfit.

will help, like Nordstrom, I know has some. It's just that I know most people myself included listening to this probably can't afford like a custom leather jacket for example.

But let's say you want a little bit more of a rugged biker look, then maybe you go to Self Edge. If you want a very minimalist look, maybe you look at Lamaire and you know there are going to be kind of more affordable. Some listeners are going to look up Lamire and be like, this guy really recommended a shop that tells, you know, like six hundred dollars pants. But if you can't afford Lamire, then you can go to a store named costs CS and they have closed

that are like Lamaire. Or you could look at Lamaire's collaboration with Uniclo and they have a line called you Just Simply You, and that will have many of Lamaire's shapes, but in more not only affordable prices, but more affordable material so that you're not paying for like a silk shirt for example. And yeah, I think you start with the aesthetic that you want to create and then find

stores that specialize in that look. And one way is if you find a store or brand that you really like, go to their Instagram account, click the tag section, and then you'll see a bunch of people who are posting photos of outfits with those garments. Then you can not only follow the people that are stylish that you would like to kind of emulate, but you can also look

at the other brands that they're wearing. So let's say you find that you really like prep and you discover a store called Sidmashburn, which is really good for that look, and you go to Sidmashin's Instagram and you click the tag section. You see all these people wearing Sidmashburn stylish ways, and you click their photos and you find out, oh, I can also check out I don't know mercer for button down shirts and Ratio clothing for you know, chinos

and other types of button ups. That's a way that you can essentially discover new brands and then go deeper in the wrap. You know, on those pages, you can colick the tag seession, you start following certain accounts, you learn about certain brands, and you start saving photos. You can either bookmark them in Instagram or you can save them on your phone. Or your computer or whatever. And I think over time you just start refining your tape

and figuring out what works for you. It obviously helps if you can if you're lucky enough, This does not always work, but if you can find people online that are built similar to you, So if you're a heavier guy, it certainly helps to find if you can find guys that are built like you on Instagram, because then you can see what brands they're buying. Yeah, so I would start there. I would start thinking about fashion and social language.

Look up brands, look up those accounts, find stylish people, follow them, save photos, and then over time you'll figure out which toures to to check out.

loves I don't know, fixing motorcycles or whatever. Well, then probably for you, I would recommend a tougher leather jacket, maybe in a motorcycle style, so that would tend to be materials like coat skin, cowhide. Those types of jackets will look heavier and more like armor, for example. And if someone was searching for that, I'd recommend them to self Edge, Standard and Strange probably carry some leather jackets. I would recommend they check out Shots, which is a

classic leather jacket maker, Lewis Leathers, Snake Oil Provisions. All of those shops have those styles. And then additionally they have the types of clothes that you can wear with that leather jacket. So they'll have the right flannel shirts and the right jeans and the right boots. You don't have to buy the entire look from one store, but you know, when you go in that store and you figure like, oh, this is the way I put together that look. Then, but you know, the flannel shirts don't

fit me. You can look somewhere else for shirts that have those qualities. But let's say you're not that type of guy and you think of yourself as kind of like I don't know, like a like the type of guy that visits wine bars, right, and you you love listening to, like I don't know, classical music or whatever, and you and you you think you look at brands

like Laura Piano and you think that's your lifestyle. Well, then you probably want a leather jacket that's made out of softer materials, not that kind of like tough, rugged armor like material So you're going to be looking at, for example, like Lambskin, and for that I would check out Valstar, which is an Italian brand. They do an A one bomber that's very quote unquote cityfied out of

softer materials. That type of jacket goes really well with Taylor trousers, like dress shirts, Shetland sweaters, chuck of boots, things like that. Who else does leather jackets like that? I assume mister Porter's in house line mister P is kind of they do these kind of like afford and I wouldn't call them affordable, but they're more affordable versions of the designer lines that they sell, and mister P

will probably have designs like that. Let's say you are you don't think of yourself as either a wine bar guy, and you don't think of yourself as like the rugged motorcycle guy. You think of yourself as just kind of like a normal dad. You know, You're just like a normal dude. You don't have these strong associations. Well, then I would maybe check out, you know, instead of like a double rider, which I like, but you know, double

rider has loaded with a little bit more meaning. So instead of a double Rider, then maybe you can look at bomber jackets. So either an A one bomber or an A two bomber, and those are you know, those are a little bit more neutral. I think in terms of styling, I would look at buzz Rickson does some repo preprom bombers that people could check out. Double RL

probably has some reprom bombers. You can also just go vintage, go to a vintage shop check out like a g one Bomber for example, and a one and a two is a little bit like it's very very dad, but a G one has a furry caller essentially that I think looks a little bit more charming. And you know, you could wear that with like sweatshirt jeans, and it's not as if you're a guy that does not identify as wine bar or motorcycle jacket or motorcycle dude, then a bomber jacket might be your thing.