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10 Stylist-Approved Valentine’s Day Outfits For Every Type of Date Night

From drinks with friends to a romantic evening at home, these cute combinations are bound to impress.


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For the past two years, couples and friends alike have celebrated Valentine’s Day in a low-key kind of way, complete with takeout and streaming services as their big plan for the night. But for 2022, the holiday of love (and we mean all love — romantic, platonic, familial, etc.), will likely look a little different — and by that, we mean semi-normal. Think dinner and drinks at a fancy restaurant, bottomless brunch, and group activities. It might be a good idea to make reservations in advance, not to mention start brainstorming Valentine’s Day outfits you might want to wear for the occasion.

It’s no secret that date nights have been pretty casual since the coronavirus hit, and if getting dressed up now feels somewhat foreign to you, you’re not alone. To spark some much-needed fashion inspiration, we reached out to celebrity stylist Tiffany Briseno. Below, she weighs in on what she’d wear to some of the most popular Valentine’s Day dates. Plus, we scoured the Internet for pieces to make her visions come to life.

A Romantic Dinner Out

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For a romantic dinner with your significant other, Briseno encourages you to lean into the sweetheart role with wide-leg, high waisted trousers (preferably in a red satin) and a sweetheart neckline bustier.

“To finish the look off, [add] some large statement earrings to fill up the negative space between your plunging neckline.”


valentines day outfits

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Whether you’re brunching with your besties or sipping mimosas with your special person, Briseno tells InStyle her go-to look for the meal would be a flouncy, lightweight dress and all white sneakers.

“To keep the look casual,” she adds, “I would have an oversized boyfriend denim jacket you can drape over the shoulders for a street chic vibe.”

Happy Hour

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When Valentine’s Day falls on a workday, the best game plan for date night or Galentine’s gathering is a happy hour with your favorite drinks. For the occasion, Briseno envisions “an A-line faux leather midi skirt with a vintage tee tucked in and a herringbone blazer.” And if heels aren’t your style (or you’re dying to get out of a pair by 5 o’clock), Briseno suggests swapping them out for some sneakers.

A Cozy Night In

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Here at InStyle, we firmly believe you can keep things casual and look cute, too. Briseno whole-heartedly agrees. The key is to be intentional with your loungewear, the stylist says via email, and nothing says intentional loungewear quite like a cashmere set. “You’ll be stylish and comfortable enough for a possible sequel marathon.”

A Galentine’s Celebration

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For Galentine’s 2022, Briseno is feeling a ’90s fashion moment. “I say bring out that bodycon knit dress and 90s inspired square toe strapped sandals,” she tells us. “Finish the look off with an equally 90’s-inspired rhinestone shoulder purse for full ‘ZAZAZOO.'”

Paint & Wine

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If you’re planning an artsy outting for Valentine’s Day, Briseno recommends keeping the fit casual with a pair of lycra bicycle shorts and an oversized button-up. For accessories, “add a bit of bling with your everyday gold necklaces,” Briseno says, adding “try layering 3 to 5 in the same type of length so a cool cluster effect.”

Spa Day

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“Before you throw that robe on, arrive in a boxy cable knit turtleneck paired with knit flared pants and sneakers,” Briseno says. This way, you’ll get your relaxation on, all day long.

Ice Skating

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Hitting the rink this Valentine’s Day? Ice skating is the perfect activity to wear a full-on winter outfit. “Corduroy trousers for that luxe texture paired with a cropped puffer coat in a metallic for an extra punch,” would be Briseno’s go-to. “For winter accessories, a wool beret and matching wool gloves. Try an oversized scarf to add more shape to your look.”

A Cooking Class

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For the makeshift chef on Valentine’s Day, Briseno says your outfit shouldn’t get in the way of your creation. To avoid a catastrophe, “try a silhouette like a jumpsuit or overalls with a great pair of combat boots and a tee,” she says. “Jazz it up with a classic gold hoop.”

A Hike or Bike Ride

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If you and your loved one are hitting a trail of some sort, your ensemble should be both comfortable and flexible. “Loose faded cargo pants, Timberland boots (because those need to come back), and a plaid fleece shirt undone with a cute microfiber racerback tank,” would be Briseno’s pick. “Fleece ‘camp socks’ are  also cool here!”

This is Ask the Experts, where our favorite fashion know-it-alls share their wisdom. Just because you can trust your style instincts doesn’t mean you should have to.

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