Welcome to fantasy date night, where the stakes are high and the man on your arm doesn’t just have a kind heart or a charming sense of humor: He is famous—iconic, even!—and eternally swoon-worthy. Maybe you’d transport back in time with the wide-grinned Jack Nicholson and tango on the Studio 54 dance floor, or recline in Steve McQueen’s arms à la Ali McGraw by the pool. Or, maybe you fancy the pop stars and their private jets of today—we’re looking at you, Harry Styles and Pitbull. Here, see who twelve editors picked (anonymously!) as their dream dates—as well as a fantasy wardrobe to fit the otherworldly occasion.
1. Who: Jack Nicholson in the seventies
Date: Melting on the Studio 54 dance floor or canoodling, drinks in tow, at an Academy Awards after-party
Look: Something slinky, something minimal, and something very Anjelica Huston
2. Who: Paul Newman, not on screen but in the kitchen
Date: Dinner at his place—he’s cooking, and it’s probably organic.
Look: A charming garden swing dress with a bucolic-luxe headband to give off that all natural farm-to-table vibe
3. Who: Taylor Kitsch, as Tim Riggins from Friday Night Lights
Date: Of course, it’s a football game. But this time, he’s not getting pummeled on the field; instead the pigskin-tossing hero is right by your side. After, hit up the local watering hole for dinner and drinks.
Look: Keep it Texas casual—great jeans, a sweater, and sandals make for a touchdown ensemble.
4. Who: Pitbull, the rapper
Date: It’s all about the 305, baby. It’s about going full-on Miami—all South Beach glitz and glam—no Wynwood hole-in-the-walls for Mr. World Wide and his lady.
Look: Anything less than standout isn’t worth it. Keep it flower-fied with heaps of contrast. It’ll sow the seeds for a fruitful jet-setting union. #DALE
5. Who: Jude Law as Dickie Greenleaf from The Talented Mr. Ripley—minus the murder and the wandering eye.
Date: Spend all day running around in the sun, then duck into a clandestine little restaurant for a drink and dinner. Cap off the night with too much dancing.
Look: Something ladylike but also with a sliver-of-skin sexy, like a gingham crop top and denim mini. Keep it shoreside-friendly with slide heels.
6. Who: Steve McQueen, “The King of Cool”
Date: Pool lounging and remember, it’s two-to-one beach chaise lounge chair.
Look: Full-on Ali MacGraw in a high-waisted two-piece and a swing-by-your-side bag for those spontaneous grab-and-go moments.
7. Who: Mark Duplass, the very handsome, and very talented director
Date: Head to IFC for a supremely indie doc followed by a beer-soaked dinner in Chinatown.
Look: It’s all about mumblecore princess—a surprisingly sexy dress in plaid or a menswear-style grungy fabric, kitten-heeled boots, oversize yet tailored jacket, and underwear that reveals itself in subtle ways.
8. Who: Evan Peters from American Horror Story. Very funny, understanding, a little intense, but extremely cute.
Date: Hiking! All of Peters’s characters seem like they’ve seen a lot of rough-and-tumble throughout their many Franken-lobster-claw-hand-apparition lives. Unlike a city slicker, he can stand for a few hours in the wild.
Look: Elevated sporty—a simple sweatshirt, floral-print Spandex, a loose tank, and a pop-of-contrast cross-body bag.
9. Who: Guillaume Canet, the brooding French actor and director
Date: It doesn’t have to be Stateside. Head to the City of Love, specifically to La Cigale Récamier for soufflé.
Look: Poppy prints and a graphic pleated shift dress fit for one night in Paris.
10. Who: Harry Styles, tousled-tressed dreamboat of One Direction. Or the embodiment of a million fan girl (and boy) screams.
Date: It starts on stage, and ends with clothes. First hang backstage at a concert serenaded by the heartthrob du jour. After, you’ll have two options: Maybe you’ll jet off to Paris or Tokyo. Then, depending on where you land, opt for a late-dinner at Septime or stop by the local fish market before breakfast. Cap off the jet-set jaunt with shopping at Rose Bakery at Dover Street Market Ginza.
Look: Those who stay together, dress alike. Therefore, keep your ensemble in the style of Styles—a bomber jacket, a simple tee, black skinny jeans, and a hybrid sneaker moccasin.
11. Who: Louis Garrel, French actor with a brutish pout
Date: Be young, be free. Jump metro turnstiles, stumble into empty movie theaters with a bottle of wine, and take a long walk back home. After all, when you’re in love, that’s all you need.
Look: Vaguely late sixties with loss of innocence vibes à la The Dreamers. Show off the shoulders but keep the rest covered.
12. Who: Brad Pitt as Tristan in Legends of the Fall
Date: Kissing in a meadow that looks as if it’s just been drizzled with a thousand prairie flower bouquets.
Look: He’s a wild cowboy with golden locks and you are sweet and stunning, as is your ensemble. The frock is pink, strapless, and dainty, and the shoes are sky-high because this is a fantasy and you can walk on a heel of any height—even if you are frolicking through a hilly meadow.
