First Dates: What to Wear and What NOT to Wear

A first date outfit isn’t there to impress. It’s there so you feel good enough in it to forget about it, and put all your attention on the person across from you.

Do: Dress for where you’re going

Start with the place (here are 20 of the safest places to meet). Coffee, a museum or a walk in the park calls for fresh sneakers, good jeans and a layer you like. A sit-down restaurant or a show calls for a step up: a shirt with a collar or a great knit, tailored pants, a simple dress or a sharp jumpsuit. When in doubt, aim slightly above what you think everyone else will wear.

Don’t: Wear something for the first time

A first date is not the moment to test-drive shoes you’ve never walked in, or a fit you’re not sure about. Wear something you already know feels good, sits right and looks like you. Save the experiment for date 3.

Do: Pick 1 thing that’s yours

A watch you love, a ring with a story, a jacket in your color. A single personal piece gives the other person something to ask about, and it says more about you than a logo ever could.

Don’t: Overdo it

Loud logos, heavy fragrance, an outfit that looks like it took 3 hours. Effort is good. Visible strain isn’t. If you have to ask whether it’s too much, it probably is.

Do: Get the basics right

• Clothes that fit. Tailoring beats price every time.
• Shoes that are scuff-free and broken in.
• Fresh breath, neat hair, trimmed nails.
• Fragrance: 1 or 2 sprays, not a cloud.
• Check the forecast. Nobody looks good shivering or soaked.

Don’t: Dress for someone else

Wearing something revealing because you think it’s expected, or dressing up as a version of yourself you don’t recognize, usually backfires. The best first date outfit is the one that looks like you on a good day.

Take it for a spin

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