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How to Dress for a First Date This Summer

Outfit ideas that extend beyond “jeans and a cute top.”

Style Equations
Street Style Outfits
Photos (L-R): Edward Berthelot/Getty Images; Jeremy Moeller/Getty Images

The “what to wear on a date?” conundrum has often plagued many a fashion girl. We often consider tampering the avant-garde-ness of our wardrobe for a first romantic. That said, you still want to give your prospective partner a taste of what they’re getting themselves into—they should take you for who you really are, tabi boots and all. As a general rule of thumb, you should wear whatever makes you feel best. However, first dates are often about cultivating just the right amount of mystique. If you are still feeling perplexed—read: if the group chat has yet to put forth any viable ideas—we’ve recreated three looks that satisfy any first date need this summer. Bonus: none of them feature the overworn jeans-and-a-cute-top ensemble.

T-Shirt + Embellished Mini Skirt + Slingbacks

Photo: Jeremy Moeller/Getty Images

Temper an embellished mini skirt with an oversized t-shirt–sporting your favorite band or logo can serve as a subtle icebreaker. Add a pair of lady-like kitten heels to make it feel polished.

Box Logo Tee

Opening Ceremony
$175 $75

Bianka Sling Heels

Sam Edelman
$140

Yellow Small Scrunch Pouch

Jil Sander
$1360 $911

Knit Tank + Relaxed Denim + Boots

Photo: Edward Berthelot/Getty Images

While this knit tank feels sultry, the relaxed-leg denim keeps the overall feel easy. Add a bright bag and a pair of Western boots to keep some flair in the equation.

Orange Leonora Bag

Paloma Wool
$300 $210

Scarf Top + Plisse Skirt + Loafers

Photo: Edward Berthelot/Getty Images

Grab any silk scarf (just make sure it’s a large one) and tie it around your chest to create a flirtatious top. We especially like it paired with a Pleats Please Plissé midi skirt. Keep the look functional with a pair of loafers and socks.

Birds Shawl

Dior
$1050

Technical-pleated Midi Skirt

Pleats Please Issey Miyake
$465

The Yves Sock

Comme Si
$30

Bowery 14kt Gold-plated Necklace

Joolz by Martha Calvo
$197
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