Basic principles for dressing better.
I’ve been a toe-in rat and existed on the outskirts of the social scene for approaching a decade now, and I can confidently say (with love) that rationalist men rarely dress well.
I am drowning in a sea of reasonably-attractive men diminishing themselves in skinny jeans and free t-shirts from random events three years ago.
But you can do better. I believe in you. Honestly, it isn’t even that hard.
In this post, I’ll be teaching you two things:
The basic theory behind how to actually assemble an outfit that will instantly make you look more interesting, attractive, and put-together.
And how to find the clothes you’ll need to buy to accomplish #1. I’ll even give you a list of links to make things easy for you.
(while this post will be geared toward men, anyone could read this and get something out of it I think)
Outfit Assembly 101
I come from an art background. Assembling a good outfit is, in my opinion, a bit like trying to create a painting. You want the overall composition to feel balanced while still being interesting and nice to look at.
The biggest things I think rationalist men neglect to consider in their outfits (to the extent they give any of this any consideration at all) are color, visual weight, and detail.
Let’s look at some examples of things I’d consider Pretty Good Outfits™:
In an effort to instill in you more of the elusive thing called taste, let’s talk about why I think these outfits work.
They aren’t afraid to wear color and pattern—while none of the outfits shown here are super crazy, they also aren’t particularly plain. Check out #6′s scarf and handbag, or the rich baby blue and maroon cardigan on the man to his right (#7).
There’s a nice balance of visual weight—meaning something bright and colorful and patterned (like the yellow shirt on #3, or the quilted jacket on #9, btw these are often called statement pieces) are paired with more understated items/solid colors to balance them out. Your outfits don’t need to be insanely maximalist to still be interesting. Many men working corporate jobs with strict dress codes have a culture of purchasing statement dress socks, for example.
A decision making process I’d recommend following as a beginner here would be to limit yourself to one statement piece per outfit, and then have everything else be solid, neutral colors. Think interesting shirt + jeans, or cool trousers + plain white sweater, for example.
And small details bring it all together—notice how #1′s bag, belt, and shoes are all the same general shade of leather. Do you see how that gives the outfit an air of intentionality, of put-togetherness? Even the very casual outfit on #10 has some of this, look at how his bandana is blue like his jeans, his white t-shirt matches his sneakers, and even his belt is dark like his corduroy jacket. Your outfits don’t need to be monochromatic, but think about ways you can have an accent color appear in more than one place.
(If, like some of my male housemates you object on principle to the concept of a bag, you could color-match a part of your outfit to something like a watch strap, belt, or shoes)
The last high-level bit of analysis I want to point out here is how, despite all of the variety in terms of color, texture, and pattern, the basic formula behind these outfits is fairly simple.
We start with a pair of well-fitting pants (bonus points if they have a slightly wider leg, slim-fit jeans aren’t actually that flattering IMO) and then add either a blank t-shirt, tank top, or button-up shirt.
Add some shoes and accessories to that and you can call it a day then and there. Or, you could take it up another notch and layer something like a blazer, jacket, or cardigan.
None of these outfits are particularly brain-breaking. They’re very straightforward.
Your shopping list so far is pretty simple:
Trousers
Button up shirt
Something to layer on top
Solid-color t-shirts (no prints or logos)
And a few miscellaneous accessories
For #1-3, get two versions: one plain, one statement piece.
If you follow the advice thus far, you’ll absolutely look more attractive and put together. Your outfits will feel more intentional and curated when you add a little bit of color, pay attention to details, and consider visual weight.
But the immediate failure mode I expect many of you to fall into is that you buy those items off of Amazon like you’re checking things off of a grocery list.
Part of what makes the above outfits interesting is that the clothes themselves are interesting. They have drape, texture, structure, interesting details. They’re nice to look at.
The way to look hotter and more interesting is both to purchase higher quality clothes that fit you well (and to get things tailored, if you can) and to have those clothes say something about who you are.
Fashion is an opportunity to express yourself.
You were sorta on the right track with this when you started wearing all of those t-shirts with xkcd comics on the back, except the signal value is about as worthless as a college degree now, because everyone else wears them too.
So think about other statements you can make or personality traits you can express. Even colors you might like to wear more!
I digress. Let’s get into my list of stores to shop from.
My Favorite Menswear Stores, And How To Find Your Own
All of the clothes pictured above are real items you can purchase from the stores in this list. I could tell you where each of them are from, but I think your life will be better if you do some digging through the online stores on this list yourself.
(Also, fair warning, many of these are a bit pricey, like $150 for a shirt kind of pricey)
For the basics:
J. Crew—If you need an entirely new wardrobe, go here first.
Bonobos—Very similar to J.Crew. Nothing innovative here, but solid.
Wax London—This is J.Crew and Bonobos’s cooler younger brother.
Todd Snyder Very much in the same category as the previous three. Good, not super interesting IMO, but hey! Not everything needs to be a statement piece.
7Diamonds—If you tend to be a little sweaty/run hot, the synthetic short-sleeve shirts they carry will do wonders for your temperature regulation. Just don’t buy the pants from here, the crotch seams will tear after a few months.
Industry of All Nations—Lots of basics in a million colors with very straightforward product photos and good material quality.
For statement pieces and more interesting basic options:
Perte D’Ego—If the things you really want are super interesting shirts that will get you endless compliments, go here. They take ages to ship, but the quality is great.
Arran Studios—This is a small independent brand still gaining traction, but if you’re more into an understated workwear/modern wild-west look, they’re great.
Cord Studio—I think this brand carries some of the most interesting and well-crafted linen button downs out there. Great details.
Society of Cloth—Features a variety of smaller designers. Lots of variation in price and very fun to browse.
House of Errors—God, House of Errors has some of the coolest clothes I’ve ever seen. So much attention to detail. They release new stuff on the regular and all of it is fun and innovative. Lots of unique knits and embroidery work that elevates an outfit.
Found Co—My favorite hoodie is from this brand. They do a lot of cool things with quilting and patches, and have a very nice earthy color palette.
A Kind of Guise—One of the pricier brands on this list, but their workwear and suiting looks really fun.
Desigual—Love the button-ups from here, lots of fun textures and patterns without being too loud. Lots of art history inspired stuff.
OAS Company—I LOVE the texture and prints from this brand.
** Note that for many of the brands on the second list, lots of what they release is in the form of small micro-collections, meaning you should really consider joining their email list, or you’ll end up missing out on their best stuff. Purchasing from small independent fashion designers has pretty few drawbacks, but that’s one of them.
But how did I find all of these interesting brands, you might ask?
You’re going to hate this part, but… I’ve found the vast majority of these brands on Instagram.
The thing about Instagram is that it’s extremely happy to show you ads it thinks you’ll click on. So why not just use this power for good?
If you follow the brands above, like a few of their posts, and only engage with ads that show you menswear (better yet, menswear you like) the algorithm will turn into your own de-facto personal shopper, plumbing the depths of the internet to serve you ads from other menswear brands just like them.
Hope this helps.
It is fascinating to receive such communiqués of strange news from another star. I would not know, without your saying so, that the set of 10 pictures are intended to be good examples and not bad examples. I am not even sure that these people exist. They look like the AI-generated product images I see on Temu.
Generic tank tops and t-shirts aside, there is not a single item of clothing there that I have, or would buy, or would wear. The same applies to what I saw on the web sites of a sample of the menswear suppliers you listed.
I don’t mean this as a criticism. It’s just a completely different world from any I have inhabited.
Why? The main post is useful but I wish it had more fashion theory. Do you?
There’s plenty of general principles there, but it all seems very culture-specific, the culture being something I can’t identify but fairly narrow.
I feel like most of these men are signalling that they’re artists (which is probably counterproductive if you’re not actually an artist).
It occurs to me reading this, it’d be cool to have a followup that explicitly lays out some “good taste” with some nearby, easily mistaken “bad taste” pictures. (i.e. someone wearing colors that are too gaudy/clashing)
If that’s a thing people want I’d be happy to write it!
I agree with the importance of having both good and bad examples, even if it is somewhat subjective at the margin.
yes please!
For me at least, a good way to develop taste in X is to intentionally look at many examples of X. When I was learning web design, at some point I got an idea to just look at hundreds of random websites and listen to my feelings, without thinking of design principles at all. Really fast, flip-flip-flip. After doing it for maybe ten hours spread over several days, I found myself having a more clear design sense. It was much more effective than reading lots of articles about design principles.
Haven’t done this with clothing, but I suspect that walking outside and deliberately looking at many people’s clothing choices might help someone develop a fashion sense really quickly.
Yep, I definitely intentionally trained my fashion sense this way (but mostly online—irl is slightly better but it’s way easier to pull up many examples of a given type on the internet)
This sounds annoying if you treat it as a chore, but I was doing it as a hobby and it was a lot of fun/somewhat addictive
There’s a tacit assumption here about what men should be optimising for with their fashion choices. I don’t believe that men “not trying very hard” with their outfits is really the $20 bill on the ground it appears to be.
When I see a man dressed like the examples above, my first-glance judgments are somewhat unfavourable. To me they don’t read as smart/successful/trustworthy. Maybe they look “hot and interesting,” but for most men that isn’t and shouldn’t be especially high on the list of things to signal.
Reflecting on my own gut reactions, the outfits that most improve my first impression of other men are either professional attire or workout gear. I think this is less about aesthetics and more about what the outfit implies. I think part of why those kinds of outfits are better at impressing me involves there being pretext for why someone would wear them that isn’t “trying to look good”.
There’s also weird stuff going on where like—if I see two people on the bus, one in a poorly sized T-shirt and one in a nice collared shirt, I feel more positive about the person in the collared shirt. But if there’s additional context where I already know they’re both equally successful buisness owners, suddenly I like the guy in the T-shirt more.
Before contemplating textures and colors, the better starting question to ask yourself is “Who am I trying to impress, and to what end?”
I also notice that all of your examples are modeled by thin, young men. Some examples that are suitable for less-thin, less-young men might broaden the appeal of your advice.
I appreciate this post and am interested in dressing better. However, when I look at the examples, what occurs to me is that dressing like the example would cause me to stick out and make it obvious to others I am making a special effort, and I’d rather not do that. I’m not saying this is a good reason, but I think it is the main obstacle for me, so I thought I’d flag it! Should one ignore this instinct?
I think the assumption here is that a preference for being “attactive” and “interesting” is trivial, but I do not think this is so:
You may wish not to draw attention to yourself.
You may wish to not to be interpreted as as sexually available.
You may wish to not be interpreted as someone who puts effort into appearances.
For me, all of these are true most of the time, perhaps even all the time outside of date night, and I’d be surprised if I’m a particularly rare case.
You say that good fashion expresses something about the personality. With all the examples you gave I’m not sure what they express.
The brands you listed also seem to signal what you personally want to express. It’s less clear to me why they would be what the average rationalist wants to express.
The item that I currently wear that expresses the most about me is my Oura ring followed by barefoot shoes.
>You were sorta on the right track with this when you started wearing all of those t-shirts with xkcd comics on the back, except the signal value is about as worthless as a college degree now, because everyone else wears them too.
This seems a bit strange to me. On the one hand most of the value of pretty expensive college degrees is in the signaling and on the other hand unless the thing you want to signal is that you are different from everyone else other people wearing something doesn’t dimish the signal. If people with one characteristics all wear the same thing it becomes a stronger signal for that characteristics.
Thanks for sharing! I come from an art/design background too, and these all resonate with me as “nice outfits that I would love to wear” and I was even looking for similar clothing recently. However, this doesn’t mean that “making a statement with high quality, anrtistic, expensive clothes” passes my cost/benefit check, and I don’t think it would for most other rationalists. (Content warning for unabashed handwavy generalizations.) Let’s look at this in a few contexts: At work, people in this community usually add value with information/data and stakeholder management. Making a statement with clothing is neutral for the first, and could lean positive or negative depending on context for the second. In dating, this is signaling that you are an interesting or artistic person who cares about appearance. This definitely helps to widen the dating pool. I think this is a plus, but this can also be done with better hygiene and by getting some standard pieces that fit well. In social situations with other rats/friends/family, it seems neutral.
Overall, I think it makes the most sense to go to the pareto frontier here. You can spend 300-400 total getting some nice looking earth tone button-ups, well-fitting pants that aren’t blue jeans, trim your beard, get regular haircuts from an actual salon, shower daily, and make sure you smell decent. You can even ask Claude to help with shopping for your specific needs. After that, there’s not a lot of utility most people will get out of it.
That being said, I still got a lot of joy looking through the links you shared! You do have great taste.
A year or two ago I went on a vacation that took me to Italy, and I felt very underdressed in my what-fits-in-a-carryon clothes. What I noticed when I was there was that somehow the Italian men just knew how to wear clothes well.
I’m not someone who is very interested in fashion or who spends much mental energy on what I or other people are wearing (where I live, a frumpy middle-aged guy like me can beat the curve just by remembering to change out of his jammies), but I stopped what I was doing and watched passers-by as though it were a fashion show. I was impressed and interested and wanted to learn. I didn’t see much that was particularly flashy (though sometimes unexpected and bold color combinations) or that shouted out “expensive designer accessories and $150 shirts.”
FWIW, they almost all wore skinny-leg pants.
When it comes to slim fit jeans I have the impression that fashion changed. Five years ago they were seen as great and now they don’t? Is that accurate?
The timescale depends on who you ask but they have definitely been gradually going out of fashion for a while. The kids these days see them as centrally millennial.
This was the most interesting aside to me. I can’t say whether it’s totally what’s going on here, but I’ve noticed a real reticence in clothing advice generally to acknowledge that fashion changes preclude optimizing your wardrobe for timelessness, and that nothing stays neutral over time. I observe a lot of folks internalizing fashion dictates of one period in time as what’s “flattering”: other women my age commonly saying things like “wide leg jeans just don’t look good on my body” when younger women (critically, with the same body types) expect and prefer the look of the wider leg.
The principles here are laid out in a totally trend-agnostic way, which is super valuable to folks who haven’t thought about this much—but the examples are most notably very on-trend with menswear right now. A principle might be “to most successfully communicate to others with your clothing (whatever your goals), you will need to learn some of the language that fashion is using at this moment in time.”
You might want some kind of sticker shock warning. I clicked the link that mentioned a linen shirt specialty (I like how buttondowns look on guys, but it is far more important that whatever my spouse wears be a pleasant texture to put my face on, most buttondown material fails this criterion but linen passes) and everything is circa two hundred dollars even if some of it looks really neat.
Super fair point, added!
I was going to say: you mention price only once. Lots of us would be better dressed if we wanted to spend a bunch of money on it. So a little on the cost/fashion tradeoff would be useful.
This is useful, thank you!
I was hoping for more fashion theory; the why. Why are these outfits good? Why are others bad? Saying “because people with taste like them” is useful but only the start. And rats love theories and often remember them better than principles.
I think fashion can be judged only by the impact it has on minds, yours and others you care about. What does your outfit say? There’s no such thing as a best outfit; the purpose and desired impact on the target audiences are the criteria, and one outfit can’t be best at everything.
That’s a different piece, and I’m not qualified to write it. But I would love to see it.