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 SnyderVery 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.
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.