In The Mood For Love? Try These Winter Date Night Outfits

“The date starts way before you show up on the date,” Logan Ury, director of relationship science at dating app Hinge and author of best-selling How To Not Die Alone tells Vogue. “The date starts hours before; when you’re getting into the mindset for the date. So, whether you think the date will go poorly, or you think the date will go well, you’re right,” she explains. “The way to get into the right mindset for dating is wearing an outfit that you feel great in.”

Surely, nobody actively tries to wear an outfit they feel less than great in, but high-stakes situations can lead to sartorial overthinking. There’s a lot to juggle: cultural norms to adhere to, the desire to honor your personal style, and the activity you’re doing on said date, to name a few. All valid considerations that can muddy the waters between what you may “want” to wear and what you feel you “should” wear. While your outfit may look the part, if it doesn’t get you in the right headspace, it’s already wrong.

And if you are what Ury calls a “hesitator” (someone who feels they aren’t ready to date until they’ve lost ten pounds, landed a new job, cleaned up their apartment, etc.), you can get debilitated by the task of finding a good date night outfit that helps exude confidence. “How do we reduce the friction to actually get them out there and get them dating again?” Ury asks rhetorically, “Because nobody is ever one-hundred percent ready for anything, and nobody is ever 100 percent ready for dating,” One of Ury’s solutions? Having a few fantastic date outfits ready and on hand. “Not having any clothes that are flattering, or that fit well, or that you’re comfortable in could be yet another excuse for why you think you shouldn’t go on a date,” she says.

Her recommendation is to have “three to four outfits that you feel comfortable in, that you feel make you look attractive, desirable, confident—an outfit that helps you look and feel your best. Then, you are going to bring that confident, sexy, flirty energy to the date,” she explains. In order to ensure you’ve hit the fashionable-mark is by testing it out in advance. “Make sure you have a bra that is comfortable, not one where the straps are constantly falling off, and you’re adjusting it, or your pants aren’t so tight that you can get them on, but you can’t comfortably sit at a picnic,” she explains. “A date is all about bringing your best, most confident self… part of that is having an outfit that really makes you feel your best.”

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