I’ve previously argued that nice clothes are good, actually. But this was an informal claim reflective of the fact that, all else equal, nice clothes are better. But, as elsewhere in life, all else is rarely equal. Choosing clothes and designing a wardrobe is a multivariable optimization problem, and it’s a problem everyone but nudists are forced to solve because we must wear something. Most people tackle the problem via intuitions, heuristics & biases, and vibes. But we’re aspiring rationalists. We can do better. We can wear optimal clothing, if only we bother to try.
But before we can do better, we must first not do worse. Therefore we must identify what optimal clothing is not. Optimal clothing is not a particular style. You cannot go to the Optimal Store and buy an Optimal Fit. Anyone claiming a particular style, brand, fabric, or article of clothing is optimal, full stop, is either lying, trying to sell you something, or confused about how optimization works. Optimal must always mean optimal for something, and in the case of clothing that something is mostly up to you.
Optimal clothing is also not about optimizing for one thing to the exclusion of everything else. If you only optimize for one thing the you’re unlikely to be on the Pareto frontier of fashion. Optimal clothing is not about falling for easy traps (local maxima) like “just wear whatever’s comfortable” or “wear what’s popular on Instagram and TikTok”. You’re going to have to try a little harder than that if you want your clothes to be Pareto optimized for you.
So if that’s what optimal clothing is not, what does count as optimal clothing? Clothing is optimal when you’ve optimized it across multiple dimensions at once to find the clothes that help you to live your best life. Importantly, you need clothes for how you actually live your life (or the life you aspire to have) in the body you have and the circumstances you find yourself in, not the life you imagine you could have if your body or the world were different.
Yet many people are tempted to optimize against their own delusions. I don’t say this to be mean, but to point out that we’re often confused about what’s going on in our lives because it takes skill and practice to notice how we actually are. Most of us have some convenient lies we tell ourselves, like that we’re taller or prettier or thinner or smarter than we really are, because they help us maintain an adequate baseline of psychological safety. But if we buy into our own lies we risk wearing things that don’t look good on us, like jeans that fit too tight, colors that clash with our complexion, or styles that are out of place. Finding optimal clothing demands we face reality.
If we want to avoid these pitfalls we need better information than we can generate ourselves. Many well-dressed people rely heavily on the judgments of trusted friends who will tell them if something looks good on them or not. If you have a fashionable friend, ask them for their opinions and encourage them to be honest. When they give you their opinions, even if they bruise your ego, thank them for their honesty and update on what they say. If you don’t have a fashionable friend, you can take your chances asking strangers on the internet, but be prepared to filter through a lot of noise from trolls.
Once you have an accurate sense of what’s important to you and what your body looks like, you need to figure out what to optimize for within clothing-space. This means getting familiar with the dimensions along which garments vary with respect to how good they look on you and how well they fit your life. Here’s roughly the dimensions I use to think about clothes:
color: does the color of this garment match your skin, eyes, hair, other clothes, etc.?
silhouette: how flattering is the shape this garment gives your body?
cost: how much does it cost?
care: how hard is it to launder and otherwise care for?
comfort: how comfortable is it to wear?
durability: how long will this garment last and under what circumstances?
functionality: how well does this garment meet your needs to carry things, stay warm/cool, have freedom of movement, etc.?
trendiness: how cool will other people think you are if you wear this?
style: does this garment send the right signals to other people about who you are?
composability: how easily can you combine it with the other clothes in your wardrobe?
variety: how much variety does it add to your existing wardrobe?
Play around with what exact set of dimensions to help you identify the best clothes. Your needs are not exactly the same as everyone else’s, and so you might need a finer-grained dimensional breakdown. For example, if you spend a lot of time outdoors, it might be useful to split functionality into subcategories like warmth, moisture wicking, packability, pockets, etc. Similarly, if you attend a lot of fashion-conscious social events, style and trendiness may require more nuanced evaluation. It’s ultimately up to what dimensions best help you determine how well particular garments meet your needs.
Set of dimensions in hand, you can now start your search for optimal clothing. A good beginning is to go broad and get a sense of the possibility space. If you’ve thought about clothes your whole life this may not be necessary, but many people have never given clothes much thought and are surprisingly underaware of what clothes exist, especially when it comes to thinking about what clothes they might actually wear. Pay attention to what other people wear and make a mental note of what you think looks good. Go to the mall or a shopping district and spend time wandering through various stores. Don’t go with a plan to buy anything: just look at things and notice what catches your eye. Over the course of 10 to 20 hours of such looking, you should start to get a sense of what might work for you.
Having developed a sense of what’s possible, now it’s time to find specific clothes for you. By now you should have some vague sense of what you want. Maybe you have a style in mind or you want to dress for certain occasions like work or dinner parties. For example, when I look for clothes I know I want them to fit in at the office, have conservative patterns and colors that will fit in at the Zen center, be relatively comfortable and allow me plenty of freedom of movement since I sometimes want to go on spontaneous hikes, and convey a vibe of quiet sophistication. I definitely don’t always succeed in achieving this, but it’s important to have ideas like this in mind to narrow your search.
Next I search for things I think I want, like “grey flannel shirt” or “straight-leg khaki pants”. Google, Amazon, etc. returns lots of results. I also check the websites of brands I like to see if they carry pieces that might work for me. Almost everything I find is not what I want, but that’s okay. I accept cookies and put ads to work for me. I get retargeted by companies trying to sell me things I might like, and then I check them out to see if I might like them. Eventually I find something that hits or gets pretty close to my desired location in clothing-space and buy it.
I realize not everyone wants to shop this way. Some of you hate ads or are unwilling to spend weeks waiting for serendipity to deliver you some ideal drip. Many of you would much rather take the direct approach. If so, you can follow the example of @Jacob Falkovich and putanumonit by creating a spreadsheet to score and rank clothes to determine what to buy. For example, you could make a column for each dimension you care about, score various potential purchases on each dimension, and then create a formula to do a weighted sum of the dimension scores based on how much each dimension matters to you. Then all you have to do is buy the clothes the score highest.
A word of warning, though, that this sort of spreadsheet approach can give you a false sense of objectivity. Numbers have a tendency to think there’s more certainty than there really is. Remember that you made up the numbers! It will help you realize that clothing choices are highly subjective and personal because fashion is an iterated social game and what you value will change over time. You might start out thinking you don’t care what others think, but then you dress nicer, start getting compliments, and realize you like looking nice enough to get compliments because the attention brings you joy. Or you think you’re wearing something appropriate for work, but then fashion norms evolve and suddenly you’re overdressed and perceived as out-of-touch. This can be annoying to folks hoping to “solve” clothing once and for all, but the only constant in this world is change, and you’ll have to accept that even if you don’t need to update your wardrobe every season you also can’t expect to never need to make any updates after five years.
For myself, I’m still learning and developing my fashion sense. I can write this post because I’ve been guilty of getting clothes wrong for much of my life, and I’m maybe 30% along the way to mastering fashion. So if you see me in person, don’t judge my advice or my clothing too harshly! I don’t pretend to be an expert here: I only claim to know enough from other domains to know a multivariable optimization problem when I see one. My hope is that this post will help you see what it took me far too long to figure out, and you can start dressing better sooner and reaping the benefits of doing so.
Optimal Clothing
I’ve previously argued that nice clothes are good, actually. But this was an informal claim reflective of the fact that, all else equal, nice clothes are better. But, as elsewhere in life, all else is rarely equal. Choosing clothes and designing a wardrobe is a multivariable optimization problem, and it’s a problem everyone but nudists are forced to solve because we must wear something. Most people tackle the problem via intuitions, heuristics & biases, and vibes. But we’re aspiring rationalists. We can do better. We can wear optimal clothing, if only we bother to try.
But before we can do better, we must first not do worse. Therefore we must identify what optimal clothing is not. Optimal clothing is not a particular style. You cannot go to the Optimal Store and buy an Optimal Fit. Anyone claiming a particular style, brand, fabric, or article of clothing is optimal, full stop, is either lying, trying to sell you something, or confused about how optimization works. Optimal must always mean optimal for something, and in the case of clothing that something is mostly up to you.
Optimal clothing is also not about optimizing for one thing to the exclusion of everything else. If you only optimize for one thing the you’re unlikely to be on the Pareto frontier of fashion. Optimal clothing is not about falling for easy traps (local maxima) like “just wear whatever’s comfortable” or “wear what’s popular on Instagram and TikTok”. You’re going to have to try a little harder than that if you want your clothes to be Pareto optimized for you.
So if that’s what optimal clothing is not, what does count as optimal clothing? Clothing is optimal when you’ve optimized it across multiple dimensions at once to find the clothes that help you to live your best life. Importantly, you need clothes for how you actually live your life (or the life you aspire to have) in the body you have and the circumstances you find yourself in, not the life you imagine you could have if your body or the world were different.
Yet many people are tempted to optimize against their own delusions. I don’t say this to be mean, but to point out that we’re often confused about what’s going on in our lives because it takes skill and practice to notice how we actually are. Most of us have some convenient lies we tell ourselves, like that we’re taller or prettier or thinner or smarter than we really are, because they help us maintain an adequate baseline of psychological safety. But if we buy into our own lies we risk wearing things that don’t look good on us, like jeans that fit too tight, colors that clash with our complexion, or styles that are out of place. Finding optimal clothing demands we face reality.
If we want to avoid these pitfalls we need better information than we can generate ourselves. Many well-dressed people rely heavily on the judgments of trusted friends who will tell them if something looks good on them or not. If you have a fashionable friend, ask them for their opinions and encourage them to be honest. When they give you their opinions, even if they bruise your ego, thank them for their honesty and update on what they say. If you don’t have a fashionable friend, you can take your chances asking strangers on the internet, but be prepared to filter through a lot of noise from trolls.
Once you have an accurate sense of what’s important to you and what your body looks like, you need to figure out what to optimize for within clothing-space. This means getting familiar with the dimensions along which garments vary with respect to how good they look on you and how well they fit your life. Here’s roughly the dimensions I use to think about clothes:
color: does the color of this garment match your skin, eyes, hair, other clothes, etc.?
silhouette: how flattering is the shape this garment gives your body?
cost: how much does it cost?
care: how hard is it to launder and otherwise care for?
comfort: how comfortable is it to wear?
durability: how long will this garment last and under what circumstances?
functionality: how well does this garment meet your needs to carry things, stay warm/cool, have freedom of movement, etc.?
trendiness: how cool will other people think you are if you wear this?
style: does this garment send the right signals to other people about who you are?
composability: how easily can you combine it with the other clothes in your wardrobe?
variety: how much variety does it add to your existing wardrobe?
Play around with what exact set of dimensions to help you identify the best clothes. Your needs are not exactly the same as everyone else’s, and so you might need a finer-grained dimensional breakdown. For example, if you spend a lot of time outdoors, it might be useful to split
functionalityinto subcategories likewarmth,moisture wicking,packability,pockets, etc. Similarly, if you attend a lot of fashion-conscious social events,styleandtrendinessmay require more nuanced evaluation. It’s ultimately up to what dimensions best help you determine how well particular garments meet your needs.Set of dimensions in hand, you can now start your search for optimal clothing. A good beginning is to go broad and get a sense of the possibility space. If you’ve thought about clothes your whole life this may not be necessary, but many people have never given clothes much thought and are surprisingly underaware of what clothes exist, especially when it comes to thinking about what clothes they might actually wear. Pay attention to what other people wear and make a mental note of what you think looks good. Go to the mall or a shopping district and spend time wandering through various stores. Don’t go with a plan to buy anything: just look at things and notice what catches your eye. Over the course of 10 to 20 hours of such looking, you should start to get a sense of what might work for you.
Having developed a sense of what’s possible, now it’s time to find specific clothes for you. By now you should have some vague sense of what you want. Maybe you have a style in mind or you want to dress for certain occasions like work or dinner parties. For example, when I look for clothes I know I want them to fit in at the office, have conservative patterns and colors that will fit in at the Zen center, be relatively comfortable and allow me plenty of freedom of movement since I sometimes want to go on spontaneous hikes, and convey a vibe of quiet sophistication. I definitely don’t always succeed in achieving this, but it’s important to have ideas like this in mind to narrow your search.
Next I search for things I think I want, like “grey flannel shirt” or “straight-leg khaki pants”. Google, Amazon, etc. returns lots of results. I also check the websites of brands I like to see if they carry pieces that might work for me. Almost everything I find is not what I want, but that’s okay. I accept cookies and put ads to work for me. I get retargeted by companies trying to sell me things I might like, and then I check them out to see if I might like them. Eventually I find something that hits or gets pretty close to my desired location in clothing-space and buy it.
I realize not everyone wants to shop this way. Some of you hate ads or are unwilling to spend weeks waiting for serendipity to deliver you some ideal drip. Many of you would much rather take the direct approach. If so, you can follow the example of @Jacob Falkovich and putanumonit by creating a spreadsheet to score and rank clothes to determine what to buy. For example, you could make a column for each dimension you care about, score various potential purchases on each dimension, and then create a formula to do a weighted sum of the dimension scores based on how much each dimension matters to you. Then all you have to do is buy the clothes the score highest.
A word of warning, though, that this sort of spreadsheet approach can give you a false sense of objectivity. Numbers have a tendency to think there’s more certainty than there really is. Remember that you made up the numbers! It will help you realize that clothing choices are highly subjective and personal because fashion is an iterated social game and what you value will change over time. You might start out thinking you don’t care what others think, but then you dress nicer, start getting compliments, and realize you like looking nice enough to get compliments because the attention brings you joy. Or you think you’re wearing something appropriate for work, but then fashion norms evolve and suddenly you’re overdressed and perceived as out-of-touch. This can be annoying to folks hoping to “solve” clothing once and for all, but the only constant in this world is change, and you’ll have to accept that even if you don’t need to update your wardrobe every season you also can’t expect to never need to make any updates after five years.
For myself, I’m still learning and developing my fashion sense. I can write this post because I’ve been guilty of getting clothes wrong for much of my life, and I’m maybe 30% along the way to mastering fashion. So if you see me in person, don’t judge my advice or my clothing too harshly! I don’t pretend to be an expert here: I only claim to know enough from other domains to know a multivariable optimization problem when I see one. My hope is that this post will help you see what it took me far too long to figure out, and you can start dressing better sooner and reaping the benefits of doing so.
Thanks to Justis for proofreading and feedback!