Hard Fits: Yung Chomsky
A new menswear interview series
Welcome to Hard Fits, a new interview series about menswear and the men who wear it.
Hard Fits will feature conversations with individuals from any number of fields, all of whom share one thing in common: a strong sense of personal style. I’ve synthesized my own look from a wide variety of influences—some of which rhyme with one another, some of which don’t. There’s something to learn from anyone with a firm understanding of how they want to appear and how to appear that way.
In today’s inaugural installment, I spoke with Yung Chomsky, unassuming producer and editor of True Anon, about the relationship between fitness and fashion, dressing in New York vs. dressing in San Francisco, and fire jackets.
Tell me how you became interested in menswear.
Growing up, I had no knowledge of or interest in style. I gave very little thought to how I dressed. Going into any clothing store made me super anxious. When I was 30, I got out of a long-term relationship, moved from Philly to San Francisco, and decided it was time to figure out what was up with clothes. I got really nerdy about it and started reading forums and blogs, following stylish people, and trying new things. Eventually I developed a sense of what I liked, started to meet people who liked similar things, yadda yadda yadda, I moved to New York, and here we are.
You’re a proponent and practitioner of resistance training. How do you conceive of the relationship between physical fitness and fashion?
Fashion and bodybuilding are both about understanding and manipulating proportions. It's easier to change your clothes than to change your body, but looking good — and feeling good — in clothes comes down to the interaction between the two. I got into lifting a few years before I started putting thought into dressing.
For a while I had told myself that since my body looked good, it didn't matter what I wore. Fortunately I realized the error of that mindset. Lifting weights and developing your physique opens up some style opportunities and blocks off others, but it's definitely a net positive. There's a bit of tension between trying to build muscle and caring about clothes, though: If I get much bigger or my proportions change, I won't fit into my jawns anymore. That's my girlfriend's main argument for why I shouldn't do steroids, and she makes a good point.
How would you characterize the menswear scene in New York City?
We're spoiled for options here. Obviously a ton of brands, large and small, have a physical presence in NYC. There's a huge range of vintage shops. Even though tailoring is something of a dying art, you can still find lots of expert alterationists and custom tailors in the city.
There are events happening all the time, and if you go to a few of them, you start to see the same people, so there's a sense of community that goes beyond online interactions. Shoutout to Alfargo's Marketplace, which I think has become something of a hub for this.
How would you characterize the difference between the way men dress in San Francisco vs. the way they dress in New York? As a current San Franciscan/former New Yorker myself, I can’t say I’m tremendously inspired by most of the ensembles I see on the street each day.
Well, the tech industry is the ubiquitous influence in SF, and those people dress very poorly in general. I guess there's also more of a gorp presence in SF than I see in NYC. There's just a lot more variety in NYC, a lot more people who are involved in the fashion industry or are just style-conscious in general.
I happened to be in New York a few weeks ago and swung by the first night of Alfargo’s—great tip on that—and I was struck by the enormous variety of looks on display amongst vendors and attendees. Classic tailoring, hypebeast streetwear, workwear, Blackbird Spyplane-core, punk chic Hedi Slimane imitators: every style seems to be equally en vogue at the same time.
Do you tend to subscribe to one particular style “genre” (for lack of a better term), or do you try to synthesize elements from a variety of (potentially conflicting?) sources into your own personal gestalt?
I try to have a "never say never" attitude when it comes to style (and other things). A fashion subculture is defined as much by its embrace of certain styles as with its rejection of others. I think it's good to know what you like and don't like, but I try to leave open the possibility of changing my mind. But "rugged Ivy" / Ametora have always resonated with me.
“Timeless” fashion is an oft-debated concept. I find myself struggling with it all the time: do I really believe this Beaufort will look good for the rest of my life, or am I just looking to rationalize dropping $500 on a jacket?
What’s your take on the concept?
I think "timelessness" in a literal sense is an illusion; people love to think that whatever was cool when they first took an interest in fashion will always be cool, which is obviously not true. But trendiness is a spectrum; some things have less staying power and will look dated more quickly than others.
How do you shop for clothes? Any guiding logic or philosophy?
At this point I've got most of my bases covered, so I'm pretty selective with adding new pieces, although I play it a little looser when it comes to vintage. If I'm gonna buy something new, it either needs to be something really special, or something I'm having made custom. I prefer to buy things I've handled in person whenever possible. There are still a few classic pieces I've been thinking about for a while, though. I've never had a seersucker suit, or a duffle coat; maybe this is the year for those.
Ok, time for the fun stuff: best store in New York City?
The Ralph Lauren flagship in the Rhinelander Mansion. Going in there is like stepping into another world. Honorable mentions to The Armoury, 10 Ft. Single, and Front General Store.
Favorite season to dress for?
Fall/winter for sure. I like layering, tweed, corduroy, flannel, turtlenecks, and dramatic coats. But I really value having four seasons. I lived in San Francisco for 5 years, and it's lovely there, but the weather is kind of the same year-round.
When putting together a fit: pants first or shirt first?
It could start anywhere: pants, shirt, shoes, jacket, sweater, tie, even headwear. It's about what's in my closet that I'm excited to wear, or what I've recently seen someone else wearing that inspired me.
Jeans of preference?
I have two pairs that I love: vintage 501s and Sugar Cane 1947s. I've never been a huge denimhead, so those pretty much cover the gamut for me.
How many pairs of shoes do you own? I have no idea if I have too many, too few, or just enough.
16 pairs in my rotation.
Favorite jacket?
It's really difficult to choose one, but I might have to go with my Pendleton bomber.
Among the things I still have in my closet and like to wear, I think I've owned this jacket the longest. I got it at the Alameda Antiques Fair in 2015, when I was just starting to care more about how I dress. It's wool and has a bold Navajo pattern. It's warm and comfortable; it makes a statement but it's easy to wear. I wrote about this jacket in some more detail, as well as a couple other favorites from my closet, for TrueAnon's Crackpots newsletter a few months back.
Honorable mention to this incredible vintage Polo jacket I got on eBay; 80/20 silk/linen.
Where can people follow you? Besides True Anon, what should they look out for from you?
I'm yungchomsky on Instagram. I've been developing an iPhone app called phomo for the past year, and I'm really excited about it. It started as a way to better catalog my daily fit pics, but it's grown into a full-fledged photo library and editing app, with film emulations, background swapping, and lots more.
Follow Yung Chomsky on Instagram
King
Has YC been on Jokermen?