These First-Date Outfits Will Make You Want to Start Swiping Again

Cheers to cuffing season and bold tops!

Looks from the Chanel Fall 2015 collection.

The first Sunday of the year is apparently the busiest day for dating apps. Call it “cuffing season” or a New Year’s resolution that stems from incessant nagging and loneliness or a certain fast-approaching February holiday, but whatever the reason, people are swiping into 2020 at record speeds.

Perhaps you took the plunge and began shopping for a partner. At first, you’re met with a slew of fluffy dogs, solo shots taken in front of the Vessel (if you’re looking in the Tri-State area) and individuals who proclaim a love of travel. Swipes and hearts turn into chats and before you know it you’re making plans to meet up with this person who really visited Hudson Yards and took a picture with the honeycomb-like structure.

Whether it be evening drinks at a chic cocktail bar or a daytime coffee, the outfit you wear to try out this human you found online is of utmost importance. So in the spirit of getting back in the game, we’ve whipped up five first-date outfits that’ll make you feel extra confident going into your next Hinge meeting. We can’t promise they’ll guarantee a second date, but you can rest assured that failing to secure one won’t be your outfit’s fault. Happy shopping!

The ‘Drinks at a Chic Cocktail’ Bar Look

A colorful, body-hugging knit dress is a playful alternative to jeans. Dress up the look with black, square-toe booties and a cool leather blazer. For accessories, lean towards chunky gold jewels, which will help turn an otherwise simple outfit into one that appears only to be intentionally understated.

Mango Chunky Knit Dress, $50, available here.

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The ‘Drinks at a Speakeasy’ Look

Maybe save the Molly Goddard frock for your second romantic outing, but if you’re feeling the sheer trend, then opt for a see-through top and jeans. Pair with a statement cuff and shoes for an ensemble that’s worthy of a repeat with someone else.

Khaite Bell Sheer Speckled Tulle Top, $432, available here.

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The ‘Late-Night Comedy Show’ Look

For more of a casual vibe, seek out a shirt dress and some cowboy boots. The addition of a chain necklace and a mini croc bag will help the outfit go from country music star to street-style maven.

Musier Dress Claudia, $149, available here.

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The ‘Cultural Outing Date’ Look

When teamed with a bold silk-satin blouse, your go-to denim bottoms suddenly become special. Spritz on an alluring vanilla scent and layer on dainty necklaces, and you’ll be picking up random strangers en route to your virtual match.

Orseund Iris Le Funk Cobalt Blue, $275, available here.

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The ‘Date That Involves A Lot of Walking’ Look

Sneakers should never be out of the question when it comes to getting dressed for a special encounter. If you’re a strictly-flats person or your rendezvous involves a lot of walking, wear your comfy kicks with a slinky slip dress. Complete the look with a jean jacket and pearl earrings.