"Sometimes you have to show a little skin. This reminds boys of being naked, then they think of sex." —Cher, Clueless
While living by key "Clueless" quotes is one way to go—we think the key to first date chic is a mix of keeping it simple, cool and reflective of your personal style. Shop ten looks, from classic denim to the little red dress, that help your date never regret swiping right.
Who: Jeanna Damas
What: A pretty blouse and cropped trousers gives that ideal French girl chic.
Isabel Marant 'Etoile' blouse, $405 , matchesfashion.com .
Who: Julia Restoin Roitfeld
What: It doesn't get easier—or more eye-catching—than a red dress. Opt for sleeves for a more laid-back approach.
Altuzarra dress, $1,950 , matchesfashion.com .
Who: Kendall Jenner
What: Leather pants, trainers and a little leopard lend you and your aura a little edge.
Alice + Olivia jacket, $595, aliceandolivia.com .
Who: Lauren Santo Domingo
What: A well-fitted jacket and jeans gives a sleek yet powerful vibe.
Veronica Beard jacket, $595 , veronicabeard.com .
Who: Kate Bosworth
What: A pretty, but not too twee floral is feminine—and perfectly balanced by a leather jacket.
Erdem dress, $707 , matchesfashion.com .
Who: Evangelie Smyrniotaki
What: Skinny leather pants make a statement—worn with a cozy sweater for comfort.
Isabel Marant pants, $1,705 , matchesfashion.com .