What To Wear On Every Type Of Date

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We’ve all been there: You’re super excited about your upcoming date until the fear of what to wear sets in, sucking all the joy out of the situation. Achieving the perfect balance between stylish and approachable can be quite the challenge. Fear not, we’ve put together five adorable outfits for the most common date activities, including everything from seeing live music to meeting the parents. So you can focus on brushing up on engaging conversation topics.

Photo: Adam Katz Sinding

Meet the Parents Date

Ginny Crossbody Bag

$1,005

Salvatore Ferragamo

Bibi Butterfly Flats

$640

Sophia Webster

Sleeveless Silk Tea Dress

$1,385

Peter Pilotto

Four Square Clip-on Earrings

$846

Vaubel

Cocktail Party Date

Imitation Pearl Dangling Earrings

$68

Kenneth Jay Lane

Box Clutch with Embroidered Beading

$195

Santi

French Lover Sandals

$1,388

Aquazzura

Lisle Dress

$3,446

Roland Mouret

Formal Party Date

Black Wire Rose Earrings

$195

Oscar de la Renta

Matilda Pumps

$1,777

Givenchy

Deep V-Neck Draped Evening Dress

$3,687

Thakoon

French Plexiglas Clutch

$295

Cecilia Ma

Festival Date

Illesteva Leonard II Red Sunglasses

$290

J.Crew

Extra Thin Safety Chain Bangle

$309

Eddie Borgo

Banff Hat

$1,261

Filu Hats

Kiss Me Sneakers

$660

Charlotte Olympia

Panelled Denim Shorts

$443

T by Alexander Wang

Fringed Flannel Trapeze Top

$235

Sea

Casual Day Date

Zepella Sandals

$1,167

Marsell

Maison Martin Margiela X Mykita Sunglasses

$894

Mykita

Addition Asymmetric Layer Striped Shorts

$643

Thakoon

Pleated Hem Flared T-shirt

$718

Chloé

Japanese Shantung Straw Fedora

$199

Stetson Handmade Cary