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.