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Occasion Guide

Date night outfits.

The best date outfit feels like the best version of you: something you are comfortable in, with one detail that makes you feel great.

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Woman in a burgundy satin slip dress and black blazer on an evening street

Match the date

First date drinks

  • Fitted top or silky camisole
  • Straight-leg jeans
  • Heeled ankle boots

Dinner out

  • Slip or wrap midi dress
  • Strappy heels
  • Leather jacket

Daytime date

  • Sundress or linen set
  • Clean sneakers or sandals
  • Crossbody bag

Date tips

Do

  • Wear something you have worn before and love
  • Choose one focal point — a color, a neckline, a great shoe
  • Dress for the venue

Don’t

  • Debut shoes that hurt
  • Wear something you will fidget with all night

Frequently asked questions

What should I wear on a first date?

Something comfortable that you already know looks good — great jeans with a nice top, or an easy dress — matched to the venue.

What should I wear for an anniversary dinner?

Dress up a level: a slip or wrap dress, or a silky top with tailored trousers.

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