A Few Rules I Actually Follow
What Does It Mean to Be Overdressed Now? · a two-part series
- Part 1: What Does It Mean to Be Overdressed Now?September 29, 2026
- Part 2: A Few Rules I Actually Follow ← you are here
Part 1 was about why the old rule stopped being enough. This part is the list I actually use: the specific calls people ask me about most, the rules I won't bend on, and the grooming and fragrance habits that do as much work as the jacket.
What that actually looks like
A few situations people ask me about most, translated into an actual outfit:
- Wedding, evening, black tie optional: a dark suit or a tuxedo, your choice, with a real tie and proper shoes. A sport coat isn't in the running.
- Wedding, informal daytime: a lighter suit or odd jacket and trousers, tie optional. Save the tuxedo for evening, and check the invitation before assuming a daytime slot settles it for you.
- First dinner with someone's parents: a sport coat over a button-down beats a full suit, which can read like an interview for the relationship instead of a visit.
- A work dinner with executives you don't know well: one notch above your own team's daily standard, not the executives'. You're representing your group, not auditioning for it.
- A backyard cookout: assume casual unless the invitation tells you otherwise. Showing up dressed past it just says you skipped that part.
- A funeral: dark and unremarkable, nothing that draws an eye, or a nose, across the room. No perfume. This is the one occasion where blending in is the entire point.
- A job interview: a notch above what the office actually wears day to day, checked beforehand against the company's own team photos if you can find them.
Texture over trend
Fit gets most of the attention, but texture is where an outfit starts to look considered instead of assembled. I usually prefer contrast in texture and proportion over adding more pattern. A chambray shirt looks more thought-through against fine-wale corduroy than against flat cotton chinos, and a smooth shirt reads better under a textured knit than under another smooth layer. I like the same kind of contrast in silhouette: a fitted top over a fuller leg, a wide-leg or barrel-cut trouser, rather than two fitted pieces together. That's a preference, not a rule; plenty of well-dressed people build the outfit the other way.
Rules I won't bend on
A short list I'd apply no matter what the room is doing:
- Cargo pants and cargo shorts belong to people who need the pockets for a job, construction, carpentry, plumbing, not to whatever trend cycle keeps trying to bring them back.
- Socks with sandals are a mistake no context excuses, however confidently it keeps coming back around.
- White socks with black shoes are also a no-no, unless you're a Michael Jackson impersonator.
- One subtle necklace, one or two rings. Past that you'd better actually be in the band. Accessories should read as chosen, not accumulated.
- One watch. Two doesn't read as interesting; it reads as a decision you couldn't make.
- Suspenders or a belt, never both. They do the same job. Wearing both looks like you don't trust either one to do it.
- Take the brand label off your jacket sleeve. It's stitched there for the salesman, not for you. Let the person admiring the jacket wonder instead of read it off your arm.
Grooming counts as dressing
Clothes are the part people mention, but grooming does half the work before anyone notices the jacket. A sharp suit over an overgrown haircut or three days of patchy stubble undercuts the whole effort. Beard or clean-shaven both work fine; a beard that's neither, grown out just short of a real one, doesn't.
Hands stay in view for the whole meal, so neglected nails are more visible than people think. Keep them trimmed, and clean underneath. Chapped lips are a small thing, and an easy one to fix, so there's no reason to leave them that way. Nose hair and ear hair are the two things everyone else can see and nobody will ever mention to you directly, which is exactly why they're worth checking yourself rather than finding out secondhand.
None of this is vanity. It's the same instinct as ironing a shirt: the details handled in private are what make the effort in public look effortless.
Condition beats cost. A modest jacket that's clean, pressed, and cared for usually reads as more deliberate than an expensive one that's been neglected. Clean shoes, no obvious lint, no heavy pilling, a collar that isn't frayed or worn at the edges: that's most of the work, and none of it costs anything but attention.
A few sprays, not ten
A common starting point for an eau de parfum is two or three sprays, held about five inches from the skin, aimed at a pulse point like the wrist or the base of the throat, then left alone to dry down instead of rubbed in. Rubbing can change how a scent develops. Past a certain point, another spray mostly makes your scent cloud larger, which is the fragrance version of the outfit nobody can stop looking at. I wrote a longer piece on choosing fragrance for specific occasions, room size and standing distance rather than notes or seasons, if this is the kind of thing you'd rather have sorted out ahead of time than guessed at in the mirror.
Why have rules at all
None of this is really about the rules themselves. It's about deciding all of it before you leave the house, so you're not still working it out once you're in the room. Get dressed, check the details, then stop thinking about your clothes and pay attention to the people you're with.
That's the same idea Part 1 arrived at, from the other direction. Clothes are supposed to serve the room. The moment they start asking the room to serve them, something's gone wrong, whether that's overdressing or just not being able to let the outfit go once you've got it on.