Outfits For ANY Date You Might Have Planned

This article was last updated on April 16, 2022

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So you’ve got plans tonight. And whatever message you want to send (“I’m awesome!” “We’re awesome!” “You’re actually not that awesome… but let’s stay friends?”), we’ve got the outfit for it. 

Much like an interview ensemble, your date-night look should let your personality shine through, but never overwhelm to the point that your patterned, bejeweled collar is shouting louder than your actual voice. With that in mind, we’ve pinpointed the five most common date-night scenarios and paired ’em with the bodacious, sophisticated outfits that are perfect for each. Now, if only there were a guarantee that your date would follow the same rules….

The First Date — For the crucial first date, keep things basic and covered up, but with the opportunity to do a little flirting. We like starting with a basic silk camisole and a nighttime blazer, and spicing things up with a mid-thigh skirt. 

Clockwise from the top left: Miss Selfridges Aztec Necklace, $18, available at Miss Selfridge; AllSaints Kovach Blazer, $295, available at AllSaints; La PerlaBlack Silk Cami Top, $120, available at Stylebop; Felder Felder Jill Embellished Metallic Leather A-Line Skirt, $310.50, available at The Outnet; Zara Ankle Boot with Metal Toe, $159, available at Zara.

The “Let’s Be Friends” Date — Man repelling is the name of the game here, but you still want to look fashion-forward and confident. This is your chance to try out some brave new trends like printed trousers and oversized vests.

Clockwise from the top left: Topshop Medallion Trousers, $80, available at Topshop; 3.1 Phillip Lim Vest, $486.50, available at Farfetch; Chan Luu Sequin Long Sleeve Top, $275, available at Calypso St. Barth; Pieces Kitt Earrings, $12.31, available at ASOS; Reiss Kristina Lace Up Bootie, $370, available at Reiss.

The Anniversary Date — You two have been together for what feels simultaneously like eons anda hot second. Up the fancy quotient (because this ain’t a regular Friday night bar hop for the two of you) with classic shoes, a pretty coat, and a body-hugging dress.

Clockwise from the top left: Marni Coat, $1,980, available at Marni; French Connection Dakota Baby Dress, $298, available at French Connection; J.CrewCrystal Starlet Earrings, $35, available at J.Crew; Kate Spade Normandy Park Dot Bag, $298, available at Kate Spade; Karen Millen Black Pump, $199, available at Karen Millen.

The At-Home Date — If you’re going to be spending the evening in, we like the idea of a cozy sweater worn with a pair of pants that have a bit of stretch to them (in case you’re going to be doing some couch cuddling). And in case things go well? Pretty lingerie!

Clockwise from the top left: BCBG Tribal Beaded Necklace, $88, available at BCBG; rag & bone Jean, $242, available at Otte; H&M Sweater, $34.95, available at H&M; Topshop Satin Soft Bra Set, $46, available at Topshop; Repetto Camille Mid Heel Ballerina, $280, available at La Garconne.

The Surprise Date — When you don’t know what the evening has in store (Apple picking? An amusement park? Dinner at The Ritz?), it’s important to cover all your bases. A wedge heel in a basic black paired with comfortable trousers, a jersey peplum top. and a moto jacket can be dressy or casual.

Clockwise from the top left: 3.1 Phillip Lim Trouser, $275, available at La Garconne; AllSaints Monolith Boot, $275, available at AllSaints; Rebecca Taylor Gina Jacket, $1,995, available at Rebecca Taylor; Mango Peplum Top, $49.99, available at Mango; Venezia Crossbody, $98, available at Nordstrom.

Market Research by Willow Lindley

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