Dressing for 90-Degree Days Without Looking Sloppy

Twenty minutes into a July walk from the train, the back of your shirt has stuck to you in a shape roughly like a map of Ohio. You’ve still got a meeting at ten, and then lunch outside, and the forecast says 93°F by two.

Most advice about what to wear in hot weather tells you to wear less. That’s half right, and it’s the half that makes men look sloppy: the baggy shorts, the faded T-shirt, the sandals that slap. You can be cool and still look like you got dressed on purpose.

The plain answer: choose loose, light-colored clothes in open-weave natural fabrics like linen, seersucker and tropical wool, keep the fit close without being tight, and wear unlined shoes with no-show socks or none. Fabric and fit keep you cooler than bare skin does, and they’re what make you look sharp at 90°F.

Fabric decides almost everything

Heat is a fabric problem before it’s a style problem. What matters is how much air moves through the cloth and how fast it lets sweat evaporate. Tight weaves and synthetics trap both. Open weaves let your body do its job.

I fought linen for years because it wrinkles. I’d iron a shirt, sit on a train for twenty minutes and stand up looking like I’d slept in it. I was wrong to care that much. Linen wrinkles in soft, broad folds that look lived-in rather than neglected, and it’s the coolest shirt fabric you can buy. I’ve made my peace with the creases, and so will you after one August.

Tropical wool surprises most people. Wool sounds like winter, but a fine, open-weave suit cloth at 7 to 9 ounces breathes better than plenty of cotton and springs back from creases overnight. If you’re wearing trousers to work in July, they should be tropical wool or linen. There’s more on what those numbers mean in my colleague’s guide to suit fabric weights.

Color matters less than people think, but it still matters. Pale colors reflect more sun, and they hide sweat better than mid-tones. Light blue and gray are the worst for showing it; white, tan and navy are the most forgiving.

What to wear in hot weather starts with your shoes

Feet sweat more than almost any other part of you, and hot, damp feet make the whole body feel worse. The fix is shoes that are unlined or lightly lined, with no-show socks or none at all.

For weekends and casual summer days, my pick is the Sperry Authentic Original Boat Shoe, at $100. It’s a hand-sewn moccasin with rawhide laces and a siped non-marking sole, built for wet boat decks and well suited to shorts and linen. The leather softens quickly and there’s very little between your foot and the air, which is exactly what you want at 90°F.

It has two limits, and both matter on a hot day. The cushioning is thin, so it’s a poor choice for a long city walk. I’d cap it at about two miles of pavement before your feet start to complain; beyond that, wear something with a real insole. And it looks out of place with anything heavier than chinos. With linen trousers, shorts or light cotton it’s right at home. With wool suit trousers, it looks like you got lost on the way to the marina.

For the office, a leather penny loafer or an unlined suede loafer does the same job with more polish. Either way, give each pair at least 24 hours between wears. Leather needs that long to dry out from a day of summer sweat, and a pair worn two days running starts to smell by Wednesday.

No-show socks are worth buying in a pack of six. They protect the lining of the shoe and keep your feet from sliding around, and nobody can see them. A light dusting of foot powder in the morning helps too.

In heat, the shoes you can’t see into matter more than the shirt everyone can see.

Shorts, if you’re going to wear them

Shorts are where most summer outfits go wrong, and almost always it’s the length. Long, wide shorts that hit below the knee look like you borrowed them. Shorts that end two to three inches above the knee look intentional.

For most men, that means a 5- to 7-inch inseam. Shorter men and men with slimmer legs suit the 5; taller men suit the 7. Leg width should be close enough that the hem doesn’t flare out. Flat-front chino shorts in khaki, navy or olive will do almost everything you need.

Wear them with a boat shoe or a canvas sneaker and a shirt with some structure, like a short-sleeve camp collar shirt or a polo, and you’ll look put together in the worst humidity of the year. The T-shirt and flip-flop combination is fine for the beach and nowhere else.

The office in July

If your office has a dress code, the heat doesn’t cancel it. It does change how you meet it. Tropical wool or linen trousers in a light gray or tan, a cotton or linen shirt that fits close through the body but isn’t tight, and a loafer will keep you as cool as anyone in a dress shirt can be.

Jackets should be unlined or half-lined. A fully lined summer jacket is a contradiction. Wear it on the walk in, take it off at your desk and put it on again for meetings.

Skip the undershirt if you can, or wear a thin one in a color close to your skin tone. A white undershirt under a light shirt shows through as soon as you sweat, and it traps heat against your back.

And empty your pockets. Light summer trousers show everything, and a thick wallet in the back pocket pulls the fabric into a lump. I switched to a thinner wallet for exactly this reason, and I haven’t gone back.

Evenings, weekends and travel

Summer evenings cool down less than you’d hope, but even a few degrees makes a difference. Linen trousers, a linen or cotton shirt with the sleeves rolled twice and boat shoes will carry you through most dinners outdoors. If it’s a first date in summer, the same rules apply: one notch above the venue, nothing that looks new.

Sunglasses are the other thing worth getting right. A pair that fits your face rather than the one a store happened to have will look better and stay on when you sweat; there’s a fit guide to bridge, lens and temple sizing if you want to understand why some pairs slide down your nose.

If you’re flying somewhere hot, pack linen and tropical wool, and leave anything polyester at home. My carry-on plan for a week in one bag works for summer too, with a second linen shirt swapped in for the sweater. There’s more on dressing for the weather in the rest of Field Guides.

The verdict: For 90-degree days, build every outfit on breathable natural fabrics (linen and seersucker for weekends, tropical wool for the office) in a fit that skims rather than clings. For casual days, wear the Sperry Authentic Original at $100 with shorts or linen, but keep it off long city walks and away from wool trousers; for the office, wear an unlined loafer and rest each pair a full day between wears.