For years, I've taken being a classic nerd, geek, and hacker as a point of pride - eg, consciously trying to judge people by the code they produce, or whatever else they write, as opposed to judging them on their appearance, to the point that I prefer /not/ to know what my favourite authors look like. I've tried to make what strengths I can out of the resulting weaknesses, such as reducing decision fatigue by keeping a single hair-style for many years, wearing whichever t-shirt is on top of the clean shirt pile, and so on.
I'm no longer satisfied with this. I want to become stronger.
Last month, I bought a dozen button-up, collared shirts... and have noticed slight, but consistent changes in my workflow when I wear them. I want to leverage whatever other clothing-based self-improvements are within my budget.
For some years, I've worn a floppy boonie hat to shade my delicate eyes from the burning rays of the sun. (I've even been seen wearing it with a photographer's vest instead of a daypack while tromping around my hometown.) I'm thinking of trying out the 'Crasche' safety inserts mentioned in the recent Open Thread while hiking far from medical help, which would require a baseball-like cap with a sweatband. Given my proclivity for taking something that works and sticking with it for years, I might be wearing that cap for a very long time.
Thus, a multi-layered question: Which hat should I buy? Which factors should I take into account... and which shouldn't I? Are there any subreddits, forums, or other online discussion groups whose members would be willing to take this question seriously and with only a minimum of mockery?
Begin here and read up to part 5 inclusive. On the margin, getting a basic day-in, day-out wardrobe of nice well-fitting jeans/chinos (maybe chino or cargo shorts if you live in a hot place) and t-shirts is far more valuable when you start approaching fashion than hats. Hats are a flair that come after everything else in the outfit you're wearing them with. Maybe you want to just spend a few hours one-off choosing a hat and don't want to think about all the precursors. But that can actually make you backslide. If you look at their advice about hats, you'll see that pork pies and fedoras are recommended, but it's well-known how badly a fedora can backfire if you aren't very careful.
(For example, I'm still in the 'trying new t-shirts/shirts/jeans/chinos/shoes with an occasional jumper purchase' phase after about a year, 18 months. Still haven't even got to shorts. You might progress faster if you do shops more often or have a higher shopping budget. But suffice to say hats are a long way in.)
There is a known phenomenon of guys walking around with a fedora or brimmed hat or whatever with a poorly coordinated outfit, dirty clothes, odour, bad fit, etc. basically not having the basics down before going intermediate. In these cases you will lose points with a lot of people because they will cringe or think you're trying to compensate. You may or may not have been engaging in similar thinking when making this thread, but watch out for that failure mode.
Supplementary reading and good to get a yay or nay before buying something, or to get recommendations within a type of garment: /r/malefashionadvice/
Fashionability and going for safety helmets/caps might be divergent strategies though. If you were purely optimizing the former, what I say above might be relevant. If the latter, just getting some Crasches and calling it a day might be enough.
Now that looks like a good reference to start in on, given my current (lack of) knowledge of all things clothesy, and was worth starting this thread. Not all of it's going to be useful - my budget for nonessentials is roughly $100 per month, and I recently had to replace a fried laptop - but with luck, I'll at least start getting a sense of the general patterns of what's involved with fashionableness.
The summer temperatures regularly go above 30 C, so I've usually been wearing cargo shorts. In winter, usually simple black or tan... (read more)