Menswear Is A Subcultural Signaling System

This is useful for assembling a wardrobe!

Most Male Fashion Advice For Beginners Is Kinda Inaccessible

The problem I’m trying to solve here is that fashion advice (especially, I’ve noticed, by rationalists for rationalists) tends to fall into the category of either hyperspecific “this is the kind of thing I like, do that”, or hopelessly abstract “wear stuff that you like and that makes you feel confident.”

I want to get a bit more actionable with it while still acknowledging the diversity of preferences that exists.

And So

There are only so many Types Of Guy in the cultural imagination.

The concept of “menswear” exists because your clothes serve to identify you as a Type Of Guy, and attributes of that Guy are— mostly— determined by who the first people were to wear that specific style. When people talk about one clothing item “going with” another, this is sometimes about color but I’d argue it’s far more often about a general rule:

You do not want different items of clothing you are wearing to signal you are incompatible Types Of Guy.

If you don’t follow this rule, you may accidentally take on the aspect of “the Type Of Guy who is confused and unaware of others’ perceptions”, which is not a flattering Type Of Guy to be. (This is not strictly true— one can do intentional type-mixing, and many do and look good doing it— but I lack the vocabulary to explain when it is or isn’t true. It’s true enough.)

On a practical level, knowing some Types Of Guy give you a few different things:

• Recognition of the Type-Of-Guy you most closely dress as by default: “Oh, my favorite t-shirt is Rocker and all the pants I own are jeans.”

• Purchase guidance: “My wardrobe is all Heritage and I need footwear, so I should buy boots instead of loafers.”

• When dressing yourself: “These two items are both Preppy, so they’ll probably work together.”

Some Types Of Guy That One Can Dress As

There are stereotypes conveyed by each! Frequently, they are not subtle.

Preppy:

“I come from or aspire to upper-middle class respectability, and as such, I’m both trustworthy and conventional. I might be a lawyer but if I am, I’m off the clock. Maybe I went to an Ivy!”

Consistent With:

• Top: Blazers, sport coats, peacoats, oxford shirts, polo shirts

• Bottoms: Chinos, dress trousers, above-the-knee shorts

• Shoes: Loafers, dress shoes, minimalist white sneakers

NOT Consistent With:

• Top: Hoodies, bomber jackets, graphic anything

• Bottom: Joggers, denim, cargo pants

• Shoes: Combat boots, chunky sneakers, work boots

Underlying Logic

These clothes are associated with activities that require leisure time and money. See also: sailing (boat shoes, cable knits, windbreakers), golf (polo shirts), tennis (white sneakers, cable sweaters), horseback riding (jodhpurs, loafers).

Business-Casual

“I am who Patrick McKenzie is referencing when he’s talking about Dangerous Professionals. You should let me manage your 401k and/or sell you a car.”

(This is basically just Preppy at a higher formality level; if you’re working in government or in customer-facing high-trust positions you’ll be wearing a lot of this.)

Consistent With:

• Pretty much anything in the Preppy list above, EXCEPT

Inconsistent With:

• Loud or bright colors; the Serious Professional disdains all colors except for navy, gray, black and white.

• Shorts and polos, obviously. Let’s keep it on the golf course, fellas.

See also: what upper-but-not-c-suite management wears in tech firms. Salesmen.

Underlying Logic For Original Wearers

As I understand it, some companies in the 90s wanted to signal that they were more approachable than stuffy places that needed you to wear a suit and tie, and so they defaulted to dressed-up muted-color versions of… the same kind of stuff the leisure class had in abundance and liked to wear to the gentleman’s club. See also: Preppy.

Business-Formal

“I SPEAK WITH THE VOICE OF A BANK OR OTHER IMPORTANT INSTITUTION.”

Consistent With:

• Full suit (matching jacket and trousers)

• Dress shoes only

Inconsistent With:

• Everything else

See also: bankers, politicians

Underlying Logic Of Original Wearers

This one comes from the early capitalist/industrialist era; suits were originally used to differentiate professional businessmen and managers from both aristocrats and blue-collar workmen. Lower-visibility businesses at some point dropped this in favor of Business Casual because suits are a pain in the ass, but banks and other formal institutions want to signal they are Very Very Serious and thus persisted with this style.

Workwear/Americana/Heritage:

“I’m a straightforward, practical person. I have working class roots. I’m who certain politicians mean when they talk about Real Americans.”

Consistent With:

• Tops: Flannel, denim, canvas, plaid stuff. Work shirts. Plain t-shirts.

• Bottoms: Jeans, canvas pants

• Shoes: Boots of various kinds

NOT Consistent With:

• Tops: Blazers, dress shirts, polo shirts, graphic hoodies, athletic wear

• Bottoms: Dress trousers, joggers, shorts

• Shoes: Dress shoes, loafers, athletic shoes. (I think you can kinda get away with unobtrusive black Hokas + dark jeans but Claude will shame you for it.)

See also: Captain Malcolm Reynolds.

Underlying Logic Of Original Wearers

These were what you’d wear on a farm or in a factory— garments that are both tough and cheap. Work boots, lots of denim (cheap to produce, cheap to dye, tough), lots of tough canvas fabric. Plaid is practical both because it’s a cheap pattern to produce (use different colored fabrics for warp and weft, boom, you’re done) and because it hides stains way way better than single-color items.

Minimalist:

“I am a sophisticated cosmopolitan and do some kind of creative work. I’m a little bit like Steve Jobs.”

Consistent With:

• Tops: Blazers, sport coats, dress shirts, button-downs, sweaters (v-neck, crew), black turtlenecks

• Bottoms: Chinos, trousers, wool pants

• Shoes: Dress shoes (oxfords, derbies), loafers, minimalist leather sneakers

NOT Consistent With:

• Tops: Graphic tees, hoodies, leather jackets, band shirts, casual tees

• Bottoms: Jeans (usually), joggers, shorts, athletic wear, distressed anything

• Shoes: Athletic sneakers, combat boots, work boots, chunky sneakers

See also: Steve Jobs, Elizabeth Holmes

Underlying Logic For Original Wearers

I’m not actually sure on this one. This independently originated in a large number of “intellectual-coded” movements in cultures across the world at various points in the 20th century. French existentialists in the 40s, Japanese designers in the 80s, Bauhaus architects.

Here’s one hypothesis: minimalism in fashion is about signaling that one is both above material concerns (not workwear) and that one is above needing to chase fashion trends. Aesthetic minimalism emerges in culture-producing-intellectual segments of society independently any time someone needs to signal both of those things at once.

But I’m not sure, really.

Athleisure:

“I’m health-conscious and work in a casual environment (probably tech or creative industries). I might be going for a run later.”

Consistent With:

• Tops: Fitted hoodies, quarter-zips, performance fabric tees, bomber jackets, fleece pullovers

• Bottoms: Joggers (tapered, not baggy), tech pants, performance shorts

• Shoes: Clean running shoes, minimalist sneakers, slip-on sneakers

NOT Consistent With:

• Tops: Dress shirts, blazers, graphic tees, flannel, oxford shirts

• Bottoms: Dress trousers, jeans, cargo pants

• Shoes: Dress shoes, work boots

Underlying Logic for original wearers:

Emerged in the 2010s on the west coast as yoga wear (especially Lululemon) crossed over into everyday casual wear. If your office culture is hyper-casual and you live in a temperate climate, why not just build your whole wardrobe around athleisure?

Rocker/Counterculture:

“I’m a rebel and don’t care for your rules, man. Also, I might be in a band.”

(I have a black suede leather jacket and one time I wore it out and someone asked if I was in a band.)

See also: greasers, rockers, Nvidia CEO Jensen Huang (lol)

Also There Are Others

This is not comprehensive, by any stretch of the imagination. Hippie, bohemian, academic— there are dozens and dozens of different Types Of Guy that one might model their wardrobe after, and the generally-legible Types Of Guy vary dramatically based on the culture you’re in. Ask Claude and you’ll get a hell of a list.

Orphaned Style Directions

Frequently, different kinds of clothes get orphaned— that is, shoehorned into representing a disfavored Type Of Guy— and people stop being willing to wear them in most contexts. This can happen for varying reasons:

Association With A Stigmatized Group

• Fedoras became memetically associated with unattractive socially-awkward men sometime in the early 2000s.

• Sleeveless undershirts worn alone are associated with poor white Appalachian men. The term “wifebeater” is popularly used for these shirts, and the term itself encodes the stigma.

Lack Of Aspirational Type-Of-Guy Associations

• Ratchet belts are really useful for growing teenagers because you can simply ratchet them to precisely the tension that’s needed without buying new belts. Similar to cargo shorts, ratchet belts thus end up in a category where you’re not strongly signaling a Type Of Guy which makes it hard to look good while wearing them.

• Velcro shoes solve critical problems for children who don’t know how to tie their shoes, and for elderly individuals who can’t work laces. Which is precisely why able-bodied men tend not to wear them.

This Is Not A Thing, Nobody Has Ever Worn This, What Are You Doing

CJ the X has a delightful youtube talk on this topic which I will not bother to summarize here.

Conclusion

Rat-adjacent men tend to resist consideration of fashion (or, if you’re a fashion nerd, “menswear”) as intrinsically shallow. Maybe it is!

Nevertheless, even if you don’t care about style, style cares about you. You are already being read by every stranger you pass on the street as a Type Of Guy and you may as well take some control over this process.