Nice Clothes are Good, Actually

This is just some casual thoughts about how to dress nice. I think dressing nice is a useful skill, but nobody told me in a way that convinced me. So this is written in the spirit of what I wish someone would have told 15 year old me.

For most of my life I thought dressing nicely was a type of bullshit signaling game I didn’t need to play because I was doing Real Work. I’m here to tell you that I was mistaken and that dressing nicely is good and useful to your life.

My story went something like this:

  • I care about doing important, meaningful things in the world, like solving hard technical problems.

  • I can solve those problems regardless of what I wear.

  • Further, lots of the people who seem best at solving hard technical problems dress poorly.

  • Also, I don’t really understand fashion that well, and most of the people who do understand it seem to be focused on things other than solving hard technical problems.

  • Conclusion: I should not care about dressing nicely. Just wear whatever is comfortable regardless of how it looks.

Dressing poorly or casually, though, is still a kind of signaling game. My reasoning makes this clear: it shows I’m part of the ingroup of serious people solving serious, real problems rather than part of the outgroup of silly people who care more about how they look than getting things done.

In some situations and in some contexts, this is a true, useful fact. If you show up to a coding interview in a suit, you’ve probably hurt your chances to getting the job. Even if your code is great, the person interviewing you is going to worry that you have expectations about the job that don’t line up with reality. And, if we’re honest, you don’t look the part, so unconscious bias comes into play.

However, unconscious bias is the start of seeing why dressing nicely, or at least intentionally, matters. Another word for unconscious bias is vibes. What vibe do your clothes put off? That is, how do you present yourself to the world? What interfaces and affordances are you giving people based on the clothes you wear?

Some examples:

  • Wearing a pot-leaf hoodie? People will reasonably think you smoke weed and that smoking weed is important to you.

  • Wearing a three-piece suit? People will think you have money (because you had enough money at least to afford the suit) and are serious.

  • Wearing a poorly fitted suit? People will think you are a low-level employee of a faceless business and you don’t have the experience or the money to dress better.

  • Wearing a sundress or a tank top and shorts? People will think you’re relaxed and out to have a nice day off.

  • Wearing yoga pants or sweat pants and graphic tee? You’re not especially concerned about your looks and just focused on getting through the day.

And on and on. If you don’t have the same associations with these clothes as I do, that’s fine. One of the tough things about clothes is that not everyone gets the same vibe from the same clothes. This makes the problem of how to dress nice harder. Doesn’t mean it’s unsolvable, just that the solutions are fuzzy.

So why should you dress nice, even given this challenge? Because dressing nice makes your vibes better and people treat you better and are more willing to accommodate your requests. This is related to the way being attractive causes people to treat you better. While you can’t easily fix your face or age or weight (though you can try), you can easily change your clothes, and clothes go a long way towards making you attractive.

What does dressing nice mean? A few things:

  • picking clothes that fit your body shape rather than whatever is in fashion or available off the rack

  • picking clothes with fabrics that look and feel nice and of high quality

  • wearing styles that reflect the image you want to portray

  • wearing clothes that fit the context (i.e. don’t wear a suit to play basketball; don’t wear gym clothes to the Vienna Ball)

How can you learn to dress nice? It’s easier than it seems. What you first have to give up is formulas about what you should or shouldn’t wear. Instead, pay close attention to how you feel when you see other people’s clothes. What do you notice about your experience? Use that as a starting point to figure out what looks good and bad and begin to build a sense of taste.

Also ask others what they think looks good and why. Some people will just say that fashionable things look good. Ignore these people. It’s not that they know nothing, but they are likely just regurgitating cached ideas about what looks good or is in. Instead, ask people how they felt when they saw what someone was wearing. It’s hard to get people to tell you the truth about how they feel about what you’re wearing, but easy to get them to tell you how they honestly feel about what others are wearing. Use the human desire to gossip to your advantage to build your training data set.

Finally, be prepared for it to take a while to figure out how to dress nice. I don’t think you’re really ever done learning the skill, though you’ll eventually reach a level where you’re successfully dressing nicely and having the desired effect on other people when they see your clothes. There’s a valley of cringe fashion choices you’ll have to pass through. Remember that if you’re coming to this as an adult, like I did, that this is normal, it’s just that most people go through this phase in the teens and twenties and basically know how to dress nicely by the time they hit 30. The good news is your brain is fully formed and you have a lot more experience, so you should be able to get through the valley faster than it would if you were doing it organically.

My final pitch: dressing nice has made my life better. I can walk into interactions and get treated better because I dress nicer than I would otherwise. I can almost feel the positive attention radiating off other people. People like to look at people who are attractive and dress nice. Do what you can to make yourself more pleasant to interact with. It’s a generally useful power you can direct to any purpose you like.