Girls have it easy. Hot day? Pop on a little cotton dress, some sandals, and you're done.
I'd like to wear sandals, too, I really would. I'm jealous of the selection you girls have. We've got flip flops and Tevas, but I'm not a drunken frat boy (anymore) nor am I a practical middle-aged lesbian (yet).
So that leaves Converse or... oxfords! I know they're not traditional hot-weather wear, but I'd pair these Rachel Comey shoes from Frances May (1013 SW Washington) with rolled-up chinos or even shorts... the right shorts.
Which are NOT a long, baggy pair. Gone! With all the biking in this town there are some fantastically muscular legs and I want to see them.
Option 1: Mid-thigh or above. I like the Dunderon shorts at Frances May because they've got a full leg, not quite so '70s gay porn. Which I guess could be a deterrent, depending on your perspective.
Option 2: Above-the-knee skinny shorts. Less daring, still cool. Adam Arnold (727 SE Morrison) makes his to measure, so no thigh strangulation. If you want options, Local35 (3556 SE Hawthorne) has a huge selection.
Sunglasses look slightly ridiculous on everyone—just buy a pair you love and own it. Winn Perry (2505 SE 11th) carries my current crush—Moscot's crystal frame with optical-grade lens—for $199.
More practical perhaps is the secret stash of super-cheap, super-cool sunglasses at Stand Up Comedy (811 E Burnside). You have to ask for them and the stock is constantly changing. It's like a sunglasses speakeasy!
As for shirts, my absolute favorite—a navy-and-white striped Russian sailor shirt—is from military surplus superstore Andy and Bax (324 SE Grand). I don't know what the hell it's made of (the label's in Russian!), but it's soft and I wear it on hot and cold days alike so I've decided it's Merino (that's $19).
I'm also a big fan of the little short-sleeve shirts from Spanish label Armand Basi at Parallel (122 NW Marshall). But, you know, you can never, ever go wrong with a shrunken Hanes white cotton V-neck. They look good on everyone—girls included.