What to Wear for Date Night, According to a Stylist

Date night can mean a lot of different things if you ask us. While there's the more traditional route of grabbing dinner or drinks with a significant other, sometimes, our big plans include family-friendly movies at home, partying with friends, or an evening dedicated to self-love. Still, no matter what occasion is on your calendar,

Date night can mean a lot of different things if you ask us. While there's the more traditional route of grabbing dinner or drinks with a significant other, sometimes, our big plans include family-friendly movies at home, partying with friends, or an evening dedicated to self-love. Still, no matter what occasion is on your calendar, clothes can add to the fun.

When deciding what to wear to date night, there's no one-size-fits-all approach. Looks can range from Rihanna's barely-there maternity wear to Cameron Diaz's casual-cool style — and everything in between. So, to help us out, we turned to celebrity stylist Tiffany Briseno, who weighed in on what to wear to date night based on where you're going. From super sexy romantic vibes to couch-ready, check out 10 stylist-approved date night outfits below.

Meet the expert

Tiffany Briseno is a Los Angeles-based celebrity stylist. Her clients include Shawn Mendes, Michelle Yeoh, and Catherine O'Hara, among others.

For a Romantic Dinner Out

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For a romantic dinner date night with your significant other, Briseno suggested leaning into the sweetheart role with wide-leg, high-waisted trousers 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," she advised.

For Brunch

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

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

However, if you're feeling fancy, an oversized black blazer works too.

For Happy Hour

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When date night falls on a workday, the best game plan is a happy hour with your favorite drinks. For the occasion, we love a classic white button-down with a maxiskirt and boots or a similar variation. Briseno envisioned "an A-line faux leather midiskirt with a vintage tee tucked in and a herringbone blazer."

For a Cozy Night In

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Here at InStyle, we firmly believe you can keep things casual and look cute. Briseno wholeheartedly agreed, stressing that the key is to be intentional with your loungewear. Nothing says intentional loungewear quite like a cashmere set. 

"You'll be stylish and comfortable enough for a possible sequel marathon," the stylist noted. 

For a Celebration with Friends

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We may be in the 21st century, but Briseno is feeling a '90s fashion moment. 

"I say bring out that bodycon knit dress and '90s-inspired, square-toe strapped sandals," she told us. "Finish the look off with an equally '90s-inspired rhinestone shoulder purse for full 'zazazoo.'"

For a Paint and Wine Night

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If you're planning an artsy outing, Briseno recommended keeping the fit casual with a pair of leggings or lycra bicycle shorts with an oversized button-up. For accessories, turn to your everyday gold necklaces, she suggested.

"Try layering three to five in the same type of length so a cool cluster effect," she added.

For a 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 said.

This way, you'll get your relaxation on all day long. For a pop of color and that something extra, throw on a puffer vest.

For Ice Skating

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Ice skating is the perfect date night activity to wear a full-on winter outfit, and "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," she said.

For a Cooking Class

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For the makeshift chef, Briseno noted your date night outfit shouldn't get in the way of your creation.

"Try a silhouette like a jumpsuit or overalls with a great pair of combat boots and a tee," she suggested.

Accessorize with classic gold hoops, she added.

For 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.

Briseno recommended "loose faded cargo pants, Timberland boots, and a plaid fleece shirt undone with a cute microfiber racerback tank." "Fleece 'camp socks' are also cool here," she told us.

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