Leave off the branding#
A designer logo across the chest tells people which shop you went to. That’s the entire message.
The usual line is that it reads as insecurity, which overstates it. What it actually reads as is an audience — it says you were thinking about who’d see it. Wearing nothing on the front says nothing about who you were dressing for, which is the more interesting position to be in.
Don’t match the set#
A pocket square that exactly matches your tie announces that both came out of the same packet.
Coordinate the tone, keep the pattern and the colour distinct, and let them look like two decisions rather than one purchase. A plain white square in a presidential fold works with almost everything and never looks like a set.
And no square at all is a legitimate choice, not a failure to accessorise. Plenty of well-dressed men simply don’t.
Leave the trend alone#
Hairstyles date faster than clothes and you can’t put a haircut back.
Undercuts and man buns are both firmly stamped with the decade that produced them. A side part, a slicked back, or a crew cut will look the same in photographs in twenty years, and they suit a far wider range of faces.
Some of these are etiquette, not taste#
Two on this list aren’t really style questions at all, and they’re the ones people get wrong most.
Never outshine the groom. At someone else’s wedding, dress conservatively and stay a step back — a stone linen single-breasted suit rather than anything that makes people look twice. Being the best-dressed man at a wedding you aren’t getting married at is a social error, not a win.
Take “black tie optional” as black tie. Optional means the host would prefer it and is being polite. Equally, don’t wear black tie when the invitation doesn’t ask for it — turning up over-dressed reads exactly as badly as turning up under-dressed, just louder.
The small stuff#
- Velcro. On shoes, and especially on a wallet. Somebody once named a velcro wallet as their single biggest dating turn-off, which is harsh and not wrong. Buckles, laces, slip-ons, leather.
- Pre-tied bow ties. Too symmetrical, too even, and it shows across a room.
- Flip-flops away from sand or a pool. Loafers, espadrilles, or proper leather sandals do the same job in public.
- Sweatpants outside a gym. Karl Lagerfeld’s line was that sweatpants are a sign of defeat, which is very funny and slightly ridiculous as a law. The practical version is gentler: linen drawstring trousers give you the same comfort and don’t look like you gave up. Wear what you like at home.
Why subtraction beats spending#
Every item here is free. Not buying the logo shirt costs nothing. Skipping the matching set costs nothing. Choosing a haircut that won’t date costs the same as one that will.
That’s the actual finding, and it’s a bit deflating if you were hoping to solve this with a purchase: restraint reads as status, and restraint is not for sale.
A few small things to try:
- Take the most-branded thing you own out of rotation for a month.
- If your tie and square match, change one of them.
- Ask for a classic cut next time rather than the one on the wall.
- Read the dress code on the invitation literally, then follow it.