How To Be (Semi)-Fashionable

“It is not a complex problem to appear nice to people! You identify the most popular targets in each of your classes, learn what they value about themselves, and give them a minimum of three relevant compliments each week. So long as they think you are agreeable, others will follow their lead.”

From The Last Graduate by Naomi Novik

I used to dress in ways that would typically be considered unfashionable. It wasn’t that I didn’t really care, but more like some combination of not caring that much and thinking that dressing more fashionably would be difficult. I now think that generally increasing the average appearance of your clothing is a relatively easy problem to solve with money, so I have produced the following step-by-step guide:

1. Pick a store (or a few stores) that has good-looking clothing.
   1. Examples of such stores include Banana Republic, Uniqlo, and Express. (Most my clothing is from Uniqlo or Express).
   2. Amazon is a bad place for novice clothes shoppers because you don’t have any quality guarantees provided by brand names.
2. Go to the store and try on everything that looks vaguely potentially appealing to you. If nothing looks appealing, try on some random stuff. You should be aiming to try on like 20 things.
   1. An important thing to check here is how well it fits on your body. In my model, fit is like 1/3-2/3rds share of what makes a piece of clothing look good, given some sort of Cobb-Douglas production function for good-looking-ness.
3. Buy some subset of the clothing that you think fits well. If you don’t think anything fits well, you’re probably wrong and you should just buy some stuff anyway. You should be aiming to spend like $200.
   1. Try to buy at least one of pants, t-shirts, jacket, casual-button-down, shorts.
4. Try to wear this clothing as much as possible over the next few weeks and months. The goal is to develop some sense of how good it looks to you, using some combination of other people’s comments and your own internal sense.
   1. If you want, you can explicitly ask people how you look. This is kind of scary. You can also take photos of yourself on different days and try to compare them. Sometimes, telling if something looks better than something else is easier than telling if something looks good.
5. In 1-6 months, go to the website of the store that you went to, scroll through the clothing, and buy things that look good to you.
   1. You’ve been to the store in person to check fit, so you should know your size for clothing from this store.
   2. If you want to buy clothes from a different store, you should probably go to the store in person.
6. GOTO step 4

The main problem that people encounter when they want to dress better is that they don’t really know what “better” is. This makes the problem of “buying good looking clothes” a strategy that they can’t execute because they don’t know how to tell what looks good. As analogy, consider a novice chess player that doesn’t know how to “play good chess moves” because they can’t recognize when moves are good. The obvious thing for this chess player to do is to practice, and that’s what the aspiring fashionable person should do also.

The underlying model is something like “the ability to tell whether or not a piece of clothing looks good takes something like time divided by skill.” If you’re good at telling whether or not things look good, you can just look at it and tell. If you’re slightly worse, you have to try it on. If your bad, you have to wear it for weeks and weeks before you can tell if you like it or not. This makes shopping for clothing difficult if you are bad at telling if things are good because you go into a store and can’t really tell if things look good or bad, so you end up paralyzed about what to buy.

The solution, as I see it, is to initially buy clothing using external signals of quality (like the brand or your friends), wear it until you can tell if you like it or not, then try again. Gradually, you’ll develop the ability to tell if clothes are good, meaning your clothes will get better with each iteration. Often times, the confusion and fear generated by the inability to tell if things look good prevent people from doing the initial bits of exploration that are necessary to figuring out what sorts of clothing they like, so they end up just wearing whatever clothing they have, i.e. free t-shirts given to them by recruiters.