Dress for the Message, Not the Attention#
The nine#
- Defaulting to flip-flops. Perforated leather shoes breathe genuinely well — the holes are there for that — and worn with no-show socks they’re barely warmer. A horse-bit loafer with linen trousers and a plain polo does more than any amount of sandal.
- All-white, all at once. White linen shirt, white chinos, white sneakers are all excellent separately. Together they’re a costume, and the full look belongs at an actual white party.
- Undershirts worn as shirts. The lightweight deep-V things sold in packs go under something. Sleeveless versions and tank tops are gym clothes, and gym clothes should stay at the gym.
- The wrong sunglasses, unprotected. Three shapes cover nearly everyone: aviators, whose teardrop suits most faces; wayfarers, a design that’s survived fifty years; and clubmasters, which give contrast without shouting. Then keep them in a soft case — leaving a pair on your chest and walking indoors is how lenses get scratched.
- Sunglasses indoors. Push them onto your head or into the case.
- Board shorts. Around 80% of men should skip them. They came from 1960s surf culture where there was a reason for the length, then got mass-produced in the eighties cut for thin, athletic bodies. They exaggerate a stomach and make a shorter, heavier build look stouter.
- Not switching to classic trunks. Elastic waist, shorter inseam. If you’re 5'6" or 5'7", the shorter cut does a lot for your proportions.
- Cargo shorts as the default. Fine as utility wear for a day out with kids. As the everyday choice they’re tired. A shorter, non-cargo cut in light grey or tan with a polo is the swap.
- Anything too tight. The look that arrives quietly after twenty or thirty pounds. If there’s material in the seams, have it let out. If there isn’t, put it away rather than wearing it.
The idea underneath#
Almost every item is the same decision: what do I want this to say?
Too-tight clothing on a genuinely fit man isn’t a fit problem, it’s a message problem — it broadcasts one thing very loudly in a room where you’d rather be known as the capable one. The cargo shorts say something too, just less deliberately.
That reframing is more useful than a list of bans, because it survives contexts the list doesn’t cover. Not “is this allowed” but “is this what I want the first ten seconds to communicate.”
Where I’d soften it#
The board shorts figure — 80% of men — is the kind of number that sounds researched and probably isn’t. And “most men shouldn’t wear X” advice tends to assume a fairly narrow idea of what a body should look like.
The defensible version is smaller and more useful: clothes cut for a build unlike yours will fight you, and swim shorts are one of the few places men never think about cut at all. That’s worth knowing without needing a percentage attached.
A few small things to try#
- Buy a soft case for your sunglasses today
- Try classic trunks alongside your board shorts and look at both in a mirror
- Move the sleeveless things to the gym bag permanently
- Before dressing for something that matters, decide what you want it to say first