I've somewhat recently had a hot weather epiphany here. Summer is my least-favorite season for the most part, and the heat is what really kills it as I like wool, tweed, layers, etc...
For both resort and home(I live by the sea in both locations), I've been using the Outlier "New Way" shorts. I have a pair of navy and a pair of tan. They look like tailored cotton shorts, and they dry extremely quickly. Four pockets, an internal drawstring, belt loops, and tough mesh pockets(for drainage), 2-way stretch, etc. You can go from beach to bar, etc., rather quickly because they dry so quickly... and they don't look like swim trunks. 8" inseam on a size 34.
Those and J Press Madras buttondown shirts, with sky/faded denim colored Vans or navy Supergas, or the old standby of a pair of Quoddy 3-eye boat shoes.
For headwear, I have a Brooks Brothers porkpie and some other brand bucket hat. Not the coolest look, but better than most of my peers out there!
If I have to get a little dressier, again(and not a paid endoresement), Outlier is my new go-to. Their "60/30 chinos" are the greatest things ever made... They have 4-way stretch, made of cotton and Schoeller fabric, repel water and stains, and you don't sweat through them, as they're great at regulating temperature. They're cut like and look like regular cotton chinos, but you could go for a jog or do yoga(!!) in them as they're so stretchy. 11" rise and 8" hem, so they're trim but not slim or low-cut if you dig. I asked them about putting a crease in them, and they weren't 100% sure about it not damaging the fabric(the only thing that I think can do that), so I've held off. They're a little dear.
I have a pair of olive ones and a pair of dark khaki/tan ones, and they can easily go a week between washes. I'd live in them if I could. I travel for a living, and they're great for that, as they wash/dry quickly and store pretty small, and repel everything.
Those and a nice madras, linen, or OC buttondown from Gitman, J Press, Michael Spencer, or Ratio, or a navy, green, or red Lacoste polo, and Alden Cape Cod cordovan loafers or tobacco suede Astorflex desert boots with mid-ankle merino wool socks. Cool evenings I have a Paul & Shark crewneck jumper(the one with the buttons on the shoulder), or a natural color Baracuta G9.
These last things are probably too "skinhead" for most of the British here, but in New England you really have to be ITK to notice. Most people just think I'm off to security detail or something, haha.