SaDCast Show Notes: Yung Chomsky, Menswear & The Left

#TheSaDCast has it’s first guest on in a couple of years and it’s none other than Yung Chomksy, the producer of the TrueAnon Podcast and a fellow menswear enthusiast.

The First Part is where he talks about his menswear journey, how it aligns with his (and our) leftist politics, and how people of his political cohort (especially on twitter) view his attire.  The Second Part focuses much more on politics, drilling down on the aesthetics of political movements, decontextualizing menswear, and reconciling our hobby with progressivism.

It’s probably the best episode of Style & Direction so far!



Yung Chomsky.

My leftist politics should come as no surprise to anyone here, whether you read behind the subtext in my blog posts and podcasts or just straight up follow my Instagram.  This political development comes not only from genuine growth and empathy, but also out of many conversations with my friends, a few of whom are in the menswear space.  One stand out is Yung Chomsky, a stylish menswear enthusiast, fellow MFA-er, and the producer of the TrueAnon podcast.

I’ve been following YC for a little over a year, as we’ve both noticed each other’s style on MFA and sent quite a few DMs to each other.  In January, I had the pleasure of meeting him IRL when he visited LA for a liveshow; he wore an epic cord suit from Drake’s and it even caught the eye of many other lefties at the show.  Ever since, he’s been a great contributor to my personal group chat as well as the Style & Direction Discord channel (accessible through Patreon).



What is so intriguing about YC is that he represents the intersection of classic/vintage menswear and left-wing politics, at least in terms of his online persona.  In reality, he’s just a Marxist who happens to be one of the best dressed people I’ve seen.  This is why I had to get him on the podcast, even if we haven’t done a true interview in years!  Luckily for us, he has all of his own equipment, as he produces a podcast and is a fellow musician.

So I hope you enjoy our long discussion with Yung Chomsky; we even had to cut it into two parts! The first part is about his own journey with menswear, how his sizable Left Twitter audience views his weekly fit dump, and a bit how the Left and aesthetics are intertwined.

We dive deeper into the last topic in our Second Part, not just about aesthetics political movements, but also about decontextualizing/reclaiming classic menswear as well as how we can reconcile our hobby with Progressivism.



Part One

  • 1:10-  Weather Talk
  • 4:20-  “Well speaking of servants,”
  • 6:00-  Young Chomsky
  • 6:25-  About TrueAnon
  • 9:55-  “We’re trying to show that some things that sound like they’re very far-out conspiracy theories in fact are very much real, and we explore some of the history around things like that.”
  • 12:05-  The Style Journey of One Yung Chomksy
  • 19:00-  “When you look at the people there, everybody behaves in some ways and dresses like teenagers, the same as they would’ve in highschool or college – which included me, and seeing that reflected back in my colleagues made me more self conscious about looking that way myself. It started to feel wrong.”
  • 22:20-  “My first stop was Reddit…where all the knowledge is stored.”
  • 28:05-  “This illustrates how important it is to have a basic vocabulary. Before you get started in buying and building a wardrobe, you really need to figure out what it is that you like. That’s the biggest way to stop you from wasting money.”
  • 33:55-  “Lookbooks from people like Drake’s was really important to me, just for the way that they do that high-low combination…I was one of those people who I think like others associate tailoring with business and formality, and realizing that’s not necessarily the case – that tailoring can be done in a playful way, or combined with workwear or casual pieces.”
  • 38:00-  Reactions to Dress
  • 42:50-  “Certain people who are not as immersed in style or menswear will have very strong and specific associations with a certain article of clothing or certain look…last week I wore a rugby shirt over an oxford – a classic preppy look – but what I heard from a bunch of different people was ‘oh Steve Bannon Steve Bannon.’” 
  • 47:50-  Dressing on The Left
  • 48:05-  “There’s this sentiment of aesthetics are bourgeois. That’s the implication sometimes, and I get that; you either need an excess of time or excess of money to really get into this stuff. If you have no free time and no free money, you cannot care about fashion. But then you can’t have any hobbies.”
  • 48:50-  “There’s the slogan we often hear on the left is ‘bread and roses,’ it comes from this speech of the worker needing bread but she needs roses too. The point being that we need to be able to survive – the bread, basics of living – but we need roses and that’s the beauty: that’s art, that’s love and laughter and mirth.”
  • 49:20-  “I get pushback of ‘oh you’re wearing expensive shoes, you’re not a socialist.’…We can talk about the shoes being expensive because they’re made domestically with labor conditions better than somewhere else, these pieces take a lot of work to make – don’t you think somebody should be compensated for making that? If I’m trying to get the cheapest thing possible, what does that say about paying the person who’s making it?”
  • 50:15-  “People on the left sometimes get into this reflexive attitude of being dismissive about things like fashion because they’ve been excluded from it, because they don’t have the time or money to get into it…I do not think it is good philosophically, politically to get the idea that caring about aesthetics shouldn’t be a part of our project.”

Part Two

  • 1:50-  Menswear & The Left
  • 5:40-  Aesthetics
  • 6:55-  “There’s an idea that the left is not cohesive or not fashionable in general. It’s a microcosm of the structural barriers or difficulties of the left movement, where the right-wing conservative movements have institutional support.”
  • 9:30-  (EW) “When I think of the Left, it’s always very nerdy/punk. When you look at the Right, they’re trying to portray themselves as the establishment; they love authority, wearing the suit…”
  • 12:20-  “Discipline and cohesiveness are good values for a movement to have, but on the other hand,  inclusiveness and openness are also kind of left values, and those can come into tension.”
  • 14:15-  “When you have a mass movement of people in the streets, I think that if there was some kind of aesthetic – not a uniform –  it would help build a group identity.  It helps build solidarity amongst people who might not have thought about it before.”
  • 19:45- “We’re trying to make a change in society, trying to convince people and change minds. This is a form of communication. So if we can reach people more effectively by having a certain look, then that is certainly worth considering.”
  • 24:00- Menswear/Vintage Communities 
  • 25:05- “This community tends to be white, wealthy, and therefore reactionary.”
  • 26:55- “When we’re talking about vintage stuff, we’re into the aesthetics and it ends there.  There’s definitely a cohort of people where for them it’s about this false, fictionalized nostalgia. They bring ‘vintage values’ into it, ‘the fifties,’ trying to get back to the social order of decades past, not just the clothing.”
  • 30:30- “If you’re into this whole idea of dressing up, it can come from this infantilized mindset of ‘well I’m going to be better than other people,’ like putting other people down instead of an expression of personal style.”
  • 33:40- “There’s so much anger and resentment…things aren’t going well for anybody right now. If you grow up in a society where you’re supposed to live a better life than your parents – inherit the world – and you don’t, people get angry. You have to reach them before bad people do.”
  • 35:10- Reclaiming & De-Contextualizing menswear
  • 35:10- “There’s an element of reclamation for some of us. I’m Jewish and you know my grandfather wouldn’t have been allowed into the country club, where the wasps would have dressed the way that now I think is cool to dress. For those who are a visible minority – Filipino, black – I think that is a much stronger type of reclamation, but I do think it’s kind of fun to think of it that way.”
  • 39:20- “One of the defining features of the postmodern era we’re living is that there is no more monoculture. Everything is accessible all the time. And so that applies to music, art, style…it’s such a cool feature of this moment in time that you can be constantly referencing everything at once or multiple things from different periods and not stuck in one time or place.”
  • 45:35- “What I want to be saying about myself with my clothes is that I am someone who cares about my presentation, I put stock into silhouette and color, patterns and shapes and that is what I want to communicate.”
  • 46:45- (EW) “I hope that when you look at my Instagram you think that it’s okay to be multifaceted, you can be different than people expect you to be, and it’s cool to have a bunch of different overlapping interests.”
  • 48:20- “Something that is very cool about menswear is that there’s just so much you can pull from historically…we look at things like ‘oh this is Italian style, this is American Ivy’ but then to other people they just see a suit.”
  • 50:20- “The Left has retreated into subculture and part of subculture is having signifiers that show to other people that you’re part of it. That’s when you can get into this stuff where you’re being very explicit in your appearance.”
  • 55:00- Ethical Consumption Under Capitalism
  • 58:35- “The idea of ‘there’s no ethical consumption under capitalism,’ it can be used in this nihilistic way of saying ‘everything made under capitalism is unethical, therefore the choices I make don’t matter.’ I don’t think that’s true, some things are worse than others and we should try to make the choices that are less bad. That being said, remembering the real goals of dismantling this system of capitalism because it is inherently exploitative, we can’t just buy from the right brands and create an egalitarian society.” 
  • 1:05:45- “The focus has to be on changing the nature of power and exploitation and not just increasing representation at the top of the hierarchy, but to dismantle that hierarchy.”
  • 1:13:15- “Brands are not your friends, is what I’m trying to say.”
  • 1:13:50- Adopting Progressivism in Menswear
  • 1:14:45- “With every (spending) option there’s going to be some bad. You should do your best to support good businesses. It’s going back to ‘well, it’s less exploited if you buy from a heritage brand or a small artisanal brand.’ The reason everyone shops at H&M is not because they make better clothes, it’s because people can afford to show up to shop.”
  • 1:17:30- “I think it’s good to buy vintage and learn all you can about the people you’re buying from and understand that sometimes buying something more expensive can mean that it’s better made and more durable so that you won’t have to replace it. But in reality, it doesn’t always mean that; buying expensive things can just mean it’s just expensive.”


Recommended Reading





A great example of the weekly YC fit dump.





Chomsky in a corduroy suit and block stripe tie.

Clearly Leftists can be into classic menswear, as Bernie Sanders does here with a plaid (madras?) tie and an OCBD)

The Black Panthers.


Filipinos in the 1930s.

Japan’s ivy enthusiasts in the 1960s.


More Filipinos in the 1930s.

Jason Jules. 

Tyrus Wong, Disney animator and artist.

Submit Your Questions & Stories

Thanks for listening and reading along! Don’t forget to support us on Patreon to get some extra content and access to our exclusive Discord.  We also stream on Twitch, which gives us a chance to play some games and talk about menswear more candidly (highlights are posted on our Youtube).


StyleandDirection | EthanMWong | SpencerDSO

The Podcast is produced by MJ and Matthew.

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