Style is a display and telegraphing of your personality.¹

Agree. I'm waiting for the footnote on the ^1 though :D

Also, unless you’re ace, you probably want her to think you’re hot

I don't think there's a single outfit that can truly make me look hot. With a tank top I could show off the fact that my arms are bigger than some people's legs, but I think I'd look like a douche. I prefer being stealthy. With a full suit I can hide most of my features, but it's very uncomfortable to wear and I can't move my arms, at least with an off the shelf suit suitable for my height.

Also, I don't want superficial people. I have a very bad experience with someone who was with me only because of my money (go back some 10-30 comments in my profile and you can read some comments about the abuse I went through). I no longer have any money whatsoever, but now I also actually don't want to look very good. Because I don't want someone who's only with me because of my looks either.

You know how you like when a lady knows how to clothes good and dresses up and looks really fucking hot?

Thing is, a short and tight-fit dress will give me a boner that lasts for days, but I'm actually more attracted to a lady in comfy looking sweats. I guess I'm a bit like George Costanza (yes, I know Seinfeld is icky nowadays with all the revelations about at least two of the main characters, but the entire show still burnt into my memory).

The one with the comfy outfit looks like she's not trying too hard, whereas the hot one may even come across as slutty. I'll take slutty for a one-night stand, but the other one is more likely to be the lady I want to wake up next to every morning if you catch my drift. Hot only gets you so far.

Like, you wouldn’t expect the same behavior and relationship from punk leather jacket guy, lumberjack, bard, thinks-hes-a-wizard, business-devil, and the guy wearing a silk button down hentai print shirt with a first-Doctor-scarf aviator goggles mirror shined shoes but fully donald-ducking it. Would you?

I get what you're trying to say here, but I prefer remaining a mystery though. I have a strong build and I shave my hair short, at first glance I'm sure it looks like I'm probably racist and homophobic, but I'm not, even though I look very close to a specific stereotype (Estonian equivalent of chavs, really). You might find me completely quiet and staring into the distance, thinking about things not even related to the social situation at hand... But then you get me going and suddenly I'm talking to everyone. Then I go off to have a 5 hour one to one conversation with someone outside where it's freezing, because I asked them for a cigarette and couldn't stop talking afterwards. Are we talking about philosophy? Engineering? Cars? The environmental collapse caused by said cars that I love so much? Terrible jokes? Who the hell remembers.

Point is, nobody knows who I am. I don't know who I am. The way I dress is generic... But that may be the most informative way to dress because I'm so many things, a lot of them so very contradictory. It's the joy of ADHD. I'm a different person every day, with different desires, different priorities, etc. I wake up one day and I want to live in a big city, work for a tech company and earn a lot of money. I wake up another day and I want to live on a farm and only do software as a hobby or not at all. Third day, I want to start my own company. Now remember when I said I don't want to look hot? I actually also want to look hot so I could bang hot women. But then on another day I don't again. I also get decision paralysis so bad that if I had to pick an outfit every morning, I'd never get out of the house. So I have the one. Black T-shirt. Basketball shorts or jeans (only in subzero temperatures). Specific socks that I find comfortable and that I can wear for more than 3 minutes without smell. It's hard to find good socks so when I finally found them, I stuck to them.

But even with my generic outfit, I can't fly completely under the radar. The black t-shirt makes me look smaller than white would, but you can still tell that my arms are ginormous, even if my biceps and triceps are hidden. In fact, with an XXL t-shirt, my arms are very tight and you can see that my shoulders are about a kilometer apart because everything is so tight in the arm-shoulder-chest area. If you know me, you see me from behind and you instantly recognize me by the fact that my lats are so wide that I go through doorways sideways in some countries. I'm not super tall, but I am BIG. This is MY outfit. A lot of people may wear similar, but I don't think too many of them get the same looks I do based on just physical appearance. Moreso when it's snowing outside and I'm still wearing my black t-shirt and my shorts when everyone else is in a coat or parka.

TL;DR: See this wall of text? It took me a few minutes to write. Then I went on to research something on Wikipedia and then I wrote for another 2 minutes or so to elaborate a few more points. This is life inside my head. If I have to start thinking about outfits, I'm cooked. I don't know how to clothes. I know how to engines, how make code out of coffee (or energy drinks) and how lift things up and put them down. I do not know how clothes.