Begin here
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.
a hot place
The summer temperatures regularly go above 30 C, so I've usually been wearing cargo shorts. In winter, usually simple black or tan slacks - they're buried in a closet, so I'm not sure if they're cotton, but they could be chinos. (My usual trouble with long pants is finding a pair with short enough legs; IIRC, I have a 28" inseam, the shortest slacks I can find are usually 30", so I generally end up informally hemming them by folding the bottoms up inside.)
a fedora can backfire
I'm leaning towards avoiding a fedora unless and until I get to the point of having at least a business-casual suit.
/r/malefashionadvice/
Another link that looks potentially highly useful; thank you kindly.
Fashionability and going for safety helmets/caps might be divergent strategies though.
Are you familiar with the "Everyday Carry" subculture, as can be seen in the /r/EDC/ subreddit? My take on the approach is that the ideal is to be as prepared as possible for life's little emergencies, without looking like you're a survivalist nut. Eg, paracord bracelets can be decorative accents - that can conceal a whole survival kit within their loops. I'm hoping to end up with a hat that just might reduce a head injury while I'm hiking, but which won't look out-of-place while I'm at a mall.
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?