19 Cute and Cozy Winter Date Night Outfit Ideas

by Sara Wennerstrom / Feb 23, 2023

Twinkling lights, freshly-fallen snow, hot cocoa by the fireplace: Wintertime sparks romance. Celebrate the season with a date night excursion, decked out in bold holiday colors, cozy fabrics, and statement accessories to boot. Try these winter date night outfit ideas for inspiration.


19 winter date night outfit ideas


Whether you’re going for a hot coffee date or going ice skating, the perfect date night outfit elevates the occasion. Make a statement on your dates this winter season with the below outfits ideas.


  1. A layered slip dress

Transform a chic, warm-weather slip dress into a winter date-night staple by layering it over a fitted turtleneck sweater or a lace, sheer long sleeve. Add a pair of ankle boot heels and the Cadence shoulder bag to create a comfortable and cute outfit perfect for an intimate dinner or semi-formal event.


  1. Jumpsuit

No-fuss and simple, just step into your jumpsuit and you’re in your winter finest. Dress a jumpsuit up or down so it fits right in at a ski resort dinner or a night at the movies. For a more laid-back look, pair your jumpsuit with some sneakers and sunnies. Or, if you want to dress it up, choose heeled booties and a pair of hoop earrings.


  1. Dad jeans and a cozy knit

For casual occasions, dad jeans and a cozy knit hit all the right notes. The outfit is comfortable and effortless, yet doesn’t miss a beat. Add a bit of cheer to the season with a brightly colored knit such as sky blue or forest green. Complete your look with a matching bag and stud earrings for a gorgeous yet simplistic look. May we recommend the vegan Maestra bag that you can wear as a backpack or a shoulder bag?


  1. Mini skirt and tights

Fewer outfits are as glam as a mini skirt and sheer black tights. Whether you choose a classic black or a gingham-style skirt, this pairing adds a feminine twist to your date night ensemble. Pair with a cozy knit and layered necklaces, and you’re ready for a night out on the town.


  1. Blazer dress and thigh-high boots

A black mini blazer dress and thigh-high boots brings sophistication and edge to wherever date night takes you. To add a little flair to your ensemble, throw on some black boxy sunnies (snow can be quite bright!) and a bright statement purse, like the Cavalla Saddle bag in a beautiful, instantly-warming fuschia.


  1. Boyfriend jeans and a sherpa jacket

For a casual date night, try out boyfriend jeans and a sherpa jacket. It’s cute and trendy without pushing the fashion envelope. Whether you prefer a neutral sherpa jacket or plaid printed one, either option will tie your outfit together and keep you cozy. Add a pair of chunky boots and stud earrings, and you’re set to jet.


  1. Button-up and oversized sweater vest

Bring on the iconic Upper East Side school-girl vibes with a sleek button-up and oversized sweater vest. The key to styling this right is to go for longer pieces while being strategic about which pieces go longer. This is what keeps this look from wading into frumpy territory.


Choose an oversized sleek white button-down, then throw over a long neutral-toned sweater vest. Then, add a pair of black tights, a short mini skirt, and a sleek scarf for the perfect semi-formal date-night look.


  1. Wide-leg leather pants and a fitted top

Leather’s warmth lends itself well to a chilly winter excursion. Balance out the wide leg of these pants with a fitted top in a coordinating color. Finish your look with a pair of kitten heels and dangle earrings to take this outfit into more formal territory.


white turtleneck and soft pink handbag 


  1. Jeans and a long cardigan

Some date nights don’t require you to go full-out on the glam. If you’re heading to a movie or a casual dinner, pair your favorite jeans with a long, cozy cardigan. The cardigan will feel like a soft blanket as you settle in for dinner or a movie, all while adding a bit of flair to your classic ensemble. Add a few cuff bracelets and bold matte lipstick to make a statement.


  1. A matching set

If you’re struggling to decide what to wear for your upcoming date night, a matching set makes the decision for you. Whether you’re going out to a winery or a cozy cafe, there are plenty of matching set options for every occasion. For a casual affair, choose a ribbed sweater set complete with wide-leg pants. Or, if your date is at a more formal venue, opt for a midi skirt and cropped sweater matching set.


Complete your look with the Aria belt bag you can wear around your chest or waist or carry as a shoulder purse or clutch. Choose a neutral hue, such as cream, or add some holiday color with a forest-inspired hue.


  1. Athleisure and a puffer jacket

For those casual date nights when you’re shopping or ice skating, choose an outfit that prioritizes comfort first. Matching athleisure sets, or leggings and a long sleeve tee with a puffer, are still put together without fuss. Add a pair of fur boots, and you’re ready for an evening full of fun.


  1. Leather pants and a blazer

Leather pants and a blazer are a polished pair. Style your leather pants with a fitted top and oversized blazer. Add a bold lip and matching crossbody bag like our Cadence Crossbody to take this look to a whole new level.


  1. Satin top and trousers

Classy, dressy, yet not over the top, a satin top and trousers is just right for a nice occasion. It’s elegant, formal, and comfortable to boot. Spice up your classic fit with some statement earrings and low heels.


  1. A pantsuit

Sharp and sure to make a statement, a pantsuit belongs at date night as much as it belongs at the office. Choose a neutral pantsuit, such as black or cream, or go bold with a holiday wine-red or deep forest green. You can play with the fabric here, too — try velvet for winter vibes.


  1. Printed pants with a neutral top

Instead of pairing bright tops with black or denim bottoms, switch things up and go for bold on the bottom. Whether you prefer a gingham style or an abstract pattern, either choice will bring the party to your date night. To bring the right balance to this outfit, pair your pants with a neutral-hued long sleeve in white, tan, coffee, or black.


  1. Turtleneck dress

If cozy cute is your go-to aesthetic this winter season, a turtleneck dress is a great date night option. A turtleneck dress lends style without skimping on the warmth. Pair your dress with a cute clutch, tall boots, and a statement belt (or a belt bag!) for a glam look.


woman wearing crossbody designer bag


  1. Corduroy bell bottoms with a cropped knit

Bell bottoms – and flared jeans in general – are back in a big way. Go for a flirty, fun, and festive look for your next winter date night with corduroy bell bottoms, paired with a cropped knit sweater. Comfy and casual, this look is effortless without sacrificing warmth or style. Add a pair of heeled ankle boots and a scarf to make your outfit pop.


  1. Leggings and a half zip

Staying home for date night? There’s an outfit for that, too. Try a pair of leggings and a half zip, so you’re not tempted to stay in pajamas while you want to impress. Not into the half-zip? A cashmere capelette hits all the comfort marks without giving up on polish.


  1. Overall dress and a turtleneck

Overall dresses aren’t just for the farm. Great for layering, pair a turtleneck underneath an overall dress for a look that isn’t too fancy but still brings elegance and style. Add a pair of tights for a bit more warmth, and complete the look with a dainty necklace and a shoulder bag.


woman in printed dress with oversized designer bag


Show up for winter date night in style


No matter what your date plans are this winter, you’ll want to go out in style. The right one-of-a-kind accessories can elevate your look to something special and meant to impress. SENREVE offers a vast collection of handbags and accessories that are bound to make a statement. With multiple styles and color options to choose from, you’ll find the perfect piece to accessorize your date-night outfit.