18 Plus-Size Date Night Outfits for Every Occasion

From sexy nights in to after-work happy hours, fashion experts share their best ideas.

18 Plus-Size Date Night Outfits For Every Occasion
Photo: Getty Images/InStyle

Whether you're going on your first or one-thousandth date, getting dressed for the occasion can be, simultaneously, exciting and stressful. There are a lot of emotions that can hinder getting ready when you're aiming to 'dress to impress,' no matter how long you've been seeing someone.

This is especially true in a pandemic-era world. You want to feel and look your best, but if for the past almost two years that's translated to stretch-waist pants and loungewear, you might not even remember how to put together your date night outfit (and you're certainly not alone in that). So where do you go for inspiration? Probably social media like the rest of us. But if you don't have time to scroll through feeds upon feeds for the perfect plus-size date night outfit idea, we've got you covered.

To save you time and, potentially, a chair full of rejected clothing combos, we reached out to plus-size stylists and bloggers for their recommendations and categorized them by the type of date you have planned. Ahead, we've rounded up 18 of their best date night outfit recs that are sure to wow.

Plus Size Date Night Outfits
Streetstyleshooters/Getty Images

A Sexy Night In

In an exclusive interview with InStyle, plus-size fashion blogger Hannah Schneider poses the question, "Why go out when you could stay in, make some hot cocoa, and curl up with your honey by the fireplace?" We agree. If you and your person have plans to, well, not make plans (wink), Schneider says her go-to outfit would be a comfy-cute matching set (she favors this one from ThirdLove), a floor-length robe, and some comfy slippers.

"Add a red lip to make the night extra sultry," she says.

Ice Skating

Dia & Co stylist Kelsey Thomas says a cozy cable-knit sweater and black leather leggings is the ideal combo for anyone hitting the ice this season. As for accessories, she suggests adding warmth "with a long faux fur coat and mittens."

Hoping to work a bit of shimmer into your outfit? "Pair the look with a gold pendant necklace and a metallic beanie," Thomas tells us.

Wining and Dining

As far as Thomas is concerned, the quintessential dinner ensemble is a ruby red dress and some sling-back heels. "Adorn with a structured black trench coat and a suede clutch for an element of fun," she says, adding that if you really want to go all-out glam, "accessorize with a simple emerald necklace and dangle earrings."

18 Plus-Size Date Night Outfits For Every Occasion
Getty Images

Cooking Together

Comfort is key when you and your significant other are playing chef, so that's the theme Schneider is sticking with for this date night outfit idea. "Slip into a pair of your baggy jeans (I love this pair from Abercrombie), a classic white tee, and a flannel to finish off the look," she tells InStyle. "Throw on a headband or a chic hat to complete the look, and you're ready to go. Fuzzy socks are recommended for maximum comfort."

A Gallery Viewing

Venues such as galleries and the theater are usually riddled with creatively-dressed people. If you find yourself attending a viewing or show, designer of limited edition and one-of-a-kind artisan wear for plus sizes at Bergdorf Goodman, Amy Zerner, tells InStyle her recommendation would be "a monochromatic top and pant outfit with a flattering, comfortable, and unique wrap to cover."


An entire afternoon dedicated to shopping? We can get behind that. Plus-size blogger Kat Stroud says thrifting is among her and her husband's favorite date activities, and the key when choosing an outfit, she says, is to be "comfortable while fashionable." Her go-to look is a peasant top and pant set from Pinecone Row. The top, she notes, has a dramatic sleeve and cold shoulder while the pants "are a work of art and I loved how the fabric moved when I walked while keeping me warm."

Plus Size Date Night Outfit
Melodie Jeng/Getty Images

A Walk In The Park

A nice walk in the park on a sunny afternoon also tops Strouds list of most romantic date ideas. To stroll with her S.O., she tells InStyle "this cozy black sweater from Eloquii that has the cutest pleated detail in the shoulder," is a staple. "I chose to pair it with denim overalls from Fashion To Figure for a crisp chilly walk in the park, and finished the look with slide on sneakers," she tells InStyle.

Rain Date

If rain is in the forecast, but you're too excited to cancel, plus-size model and TikTok influencer, Shyla Day says grab your umbrella. "There is no rain check happening here," she says via email. "Pair your little black date dress with a warm, patterned long-sleeve to update the look for the wintertime, layer a pair of fleece-lined, flesh colored leggings underneath your pantyhose, and throw on some booties. You've got yourself a rain-proof, chic, rainy date outfit."

Happy Hour

If you're meeting for drinks, CEO and founder of Crystal Cave Style, Crystal Cave recommends something a little dressy and sexy, but not over-the-top. "I love how mesh adds a subtle hint of sex appeal without trying too hard," the founder and creative director of Poppy RowI tells us. "I recently wore something similar to a first date at a pub and paired my Good American jeans and mesh bodysuit from Poppy Row with a leopard skinny belt (similar here) and sparkly sneaker slides."

Plus Size Date Night Outfits
Emma McIntyre/Getty Images for Glamour x Tory Burch


If you're heading out on a socially distant hike, Cave recommends leaving your old gym clothes at home and, instead, opting for something that feels more put-together. "I'd style the traditional leggings and a long sleeve top with a bomber jacket," she tells InStyle. "It's the perfect streetwear look, while being ready to hit the trail."

Going to the Movies

Streaming services are great, but if you're gearing up to the movies IRL (and nosh on theater popcorn) fashion stylist and founder of Swiminista Andréa Bernholtz has the perfect date night outfit idea. She envisions a white button down with a pair of cargo pants, boots, and a sweater over your shoulders. "And don't forget a cute crossbody bag," she adds.

Sporting Event

To support your team (or theirs) you could wear the team jersey, but you could also stay neutral with a pair of athletic shorts and a classic triangle Sexy bikini top," Bernholtz tells InStyle. "A bright, fun visor, bum bag, and knee-high athletic stripe socks with a white pair of trainers will finish off the look."

A Day at the Amusement Park

For a day of greasy carnival food and fast rides, plus-size TikTok sensation Jerri Cooper says a light blue ripped cropped denim jacket with a white tube top and your favorite ripped jeans is the fit. "Lace up your Air Force 1s, throw on your sunglasses, and grab your designer backpack as you walk out the door," say Cooper. "Now you're ready to have the time of your life!"

A Night On the Town

Curvy influencer and certified body positivity expert Gabrielle Richards says if you live somewhere like Miami, where it's common to go to multiple venues for date nights, layering is key. The senior brand manager of Shapermint says the brand's Empetua Scoop Neck Cami is her favorite and a "closet staple as you can wear it on its own or underneath a shirt." She also recommends adding an animal print bomber jacket to your wardrobe, "as this can work with denim, skirts, and dresses." She tells InStyle, "You can use the cami as a base layer with the bomber jacket paired with a bright pleated skirt. This look works with a fashion sneaker or heels."

Going Dancing

If you're hitting the club, you'll want a trusty dancing shoe. Plus-size influencer Toni Rogers recommends a comfortable block heel for the occasion paired with a leather dress. But if block heels aren't your style, no worries. Roger says, "you can easily change up the look by trading the heel for a bootie or over the knee boot."

Plus Size Date Night Outfits
Stefanie Keenan/Getty Images for Constellation Immersive

Netflix Marathon

Netflix (or Hulu, or Amazon Prime, Disney+, etc.) and chill is another date night activity where comfort is a priority, but Stitch Fix stylist Stephanie Valponi isn't reaching for loungewear. "My go-to suggestion is usually black denim," she tells us. "This still demonstrates a casual vibe while taking it up a notch." Fabrics like Lycra offer comfortable stretch, Valponi adds, while suggesting that the bottoms would pair well with an off-the-shoulder sweater layered over a fitted tank or bodysuit. "Adding a shacket is another great option to either layer over the total look or pair with a simple tee underneath. This will accentuate your shape while still allowing you to snuggle up on the couch comfortably."

First Date

If it's your first time meeting up with one another, fashion and celebrity stylist Kelly Augustine highly recommends keeping things cute and casual with a pair of skinny fit denim that hugs all the right places. And if it's a first time app date, she adds, "I usually go for a turtleneck."

Game Night

Have your game face on? Good. Now, add a hoodie or an oversized knit cardigan with a block heel bootie, says Augustine. The look "shows effort," she tells us, "but you're not trying too hard."

Related Articles