4 min readFormulating the perfect date night outfit is inevitably more difficult to nail down in winter than in summer. With one-and-done dresses and slip-on sandals packed away, a winter date calls for a look that combines practical warmth and flirtatious confidence.
The key to a memorable winter date night outfit is to incorporate outerwear that feels intentional rather than obligatory, worn over pieces you’re excited to reveal once you’re inside. If you’ve found yourself defaulting to the same trusty sweater-and-puffer rotation, consider this your cue to rethink the date night look.
To inspire your next evening out, we’ve curated 15 standout street style and celebrity ensembles that prove cold-weather romance is very much alive. Whether it’s first-date drinks, a bundled-up stroll through the park, or a long-awaited anniversary reservation, there’s a look to match the mood.
From Hailey Bieber’s hot-girl top-and-trouser pairing and Dakota Johnson’s alluring take on modern suiting to ELLE’s senior fashion commerce editor’s casually cool winter white ensemble, shop the best winter date night outfit ideas ahead to wear now.
Mini Skirt With Sheer Tights
A miniskirt styled with sheer tights is a go-to look for a winter date. Style a zebra-print mini like the Giggly Squad host, Paige DeSorbo, with a fitted, neutral-hued knit, and complete the look with sharp pointed-toe pumps.
Cult Gaia Callie Knit Top
Naked Wardrobe Zebra Stripe Miniskirt
Jenny Bird Tome Hoops
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A Flirty Top and Low-Rise Trousers
We can always count on Hailey Bieber for a head-turning look, and this black outfit, featuring a romantic square-neck top and low-slung, wide-leg trousers, is no exception. Throw on an oversized leather blazer and ’90s-inspired slingback pumps to finish the subtly sexy ensemble.
Kookai Ariel Low Rise Pant
Coperni Belt 65 Slingback Pumps
A (Mostly) White Ensemble
For a daytime winter date, channel Dale Arden Chong, ELLE’s senior fashion commerce editor, in a voluminous, fuzzy coat, a classic cotton tee, and an effortlessly cool pair of jeans—all in winter white tones. Finish the look with sophisticated satin mules.
Cos Cotton Long-Sleeve T-Shirt
Slvrlake Mica Wide-Leg Jeans
Winter Florals
For a look that works now and into early spring, choose a floral-print midi dress to wear under a polished cocoon coat like the one Nicky Hilton Rothschild wore during New York Fashion Week.
Alice + Olivia Waverly Cocoon Coat
Reformation Lilibet Ruffle Trim Midi Dress
Manolo Blahnik Maren Pointed-Toe Pump
Heaven Mayhem Whisp Earrings
A Playful Shearling Coat
If your date night plan involves a concert or a bit of dancing, we love Lola Tung’s bold outfit. Style a similarly rich red shearling jacket with an asymmetric skirt, pointed-toe pumps, and a mini bag.
Ducie Rochelle Shearling Jacket
Lioness Safari Midi Skirt
Aquazurra Voile Tulle Pumps
Verafied Lizard Café Mini
A Cozy Blanket Coat and Heels
Blanket-style coats, like the one worn by Bridgerton star Yerin Ha, combine comfort and elegance. Opt for a draped, extra-long coat and style it with polished silk pants and peep-toe pumps.
Mango Funnel-Neck Trench Coat
A.L.C. Naomi Asymmetric Mock Neck Sweater
Toteme Wool and Silk Slim Pants
Favorite Daughter Yara Peep Toe Pump
A Classic Midi Dress and a Lightweight Sweater
For another outfit that effortlessly adapts from winter to spring, pair a timeless A-line midi dress with a cashmere sweater (and wear it over the dress as an extra layer or tie it around the shoulders when you’re indoors).
Proenza Schouler White Label Nyssa Dress
J. Crew Perfect Cashmere Crewneck
Mansur Gavriel Soft M Tote
An Updated Coordinated Set
Emulate Dakota Johnson’s recent Calvin Klein outfit that is equally striking and understated by pairing a modern suiting-inspired top, a slinky long skirt, and knee-high boots.
Cinq à Sept Mckenna Knot Waist Shirt
Now 46% Off
Allsaints Darya Bias Cut Skirt
Marc Jacobs The Mel Leather Boots
Freja New York Mini Chrystie Bag
A Statement Jacket and Sleek Jeans
For a low-key coffee date, cozy up in a gray faux-fur jacket and high-waisted jeans. Take a cue from Natalie Bryant and finish the ensemble with slick leather booties like Natalia Bryant.
Staud Soprano Jacket
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Mother The Kick It High-Rise Flared Jeans
Loeffler Randall Thandy Ankle Boots
Madewell The Essential Leather Belt
A Classic Fair Isle Sweater and Jeans
This street-style look featuring a chocolate brown suede jacket, cuffed denim, a Fair Isle sweater, and kitten-heel boots is ideal for a casual stroll in the park and weekend brunch.
Nili Lotan Chrissy Fair Isle Cashmere
Aritzia The ’90s Vintage Lo-Rise Straight Jean
A Leopard-Print Coat and Heels
Allow the coat to take center stage with a leopard-print topper, as demonstrated by Love Story actress Sarah Pidgeon. Once indoors, let the little black dress do the talking.
Veronica Beard Svetlana Cutout Dress
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Wolford 50 Denier Sheer Tights
Schutz Lou Pointed High Heel Pumps
A Bright Pop of Color
We love an unexpected yet intentional pairing of pieces. As exhibited by Tessa Thompson, donning a bright yellow anorak-style jacket, a cropped button-down, and a top-stitch midi skirt makes for a memorable ensemble.
Thom Browne Classic Crop Cotton Poplin Button-Down
Prada Re-Nylon Blouson Jacket
Ami Midi Denim Skirt
Now 60% Off
Malone Souliers Bettina Pumps
A Knit Polo Sweater and Romantic Skirt
The preppy polo sweater continues to trend into spring. Wear it now with a pencil skirt and knee-high boots, and then top it off with your go-to wool coat to brave the cold.
Guest In Residence Port Polo
Tory Burch Embellished Mirror Skirt
Now 50% Off
Reformation Nylah Knee High Boot
Proenza Schouler Silo Shoulder Bag
A Fur-Trimmed Coat
An all-black outfit is an effortless choice for an evening out, and this Rihanna look is anything but boring. Build your look around a leather trench coat, complete with fluffy trim, as the hero piece with a sheer tee and sleek trousers.
Nour Hammour Dakota Shearling-Trimmed Leather Coat
Aritzia The Effortless Pant
Jimmy Choo Isa Embossed Leather 95 Slingback
A Romantic Dress With Western-Inspired Details
Try a romantic, Western-inspired outfit à la Lana Del Rey at the Ralph Lauren fall/winter 2026 show. Pair a ruffled maxi dress with cowboy boots, a leather blazer, and a charm necklace.
Polo Ralph Lauren Glossed-Leather Blazer
DÔEN Ischia Floral Maxi Dress
Now 50% Off
Tecovas The Annie Western Boot
Logan Tay Bleecker St. Necklace
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