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Winter Date Outfits to Try When You're Short on Ideas

People, Urban area, Street fashion, Eyewear, Street, Fashion, Cool, Snapshot, Jacket, Glasses,
Christian VierigGetty Images

Winter date nights can be romantic. Indoor bars and candlelit restaurants feel charming and inviting, all while giving you the perfect excuse to cozy up to the person you're seeing. (It's dark! And the music is loud!) Which all sounds fun—when you're not being blasted by strong gusts of wind or pelted with hail when you step outside, that is. You have to take in all these factors for wintertime dates, which affects how you'll dress for said dates. Don't worry; we have all your cold-weather battle outfits ready for every chick-flick-approved date spot. Let the snuggling commence.

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Saturday Night Dinners
Clothing, Trench coat, Coat, Overcoat, Purple, Outerwear, Footwear, Violet, Pink, Fashion,
Design by Morgan McMullen

It's been forever since you both actually left the house to do a proper sit-down dinner date, so dress up to celebrate. Don't let winter stop you from slipping into a dress, like this sleeved one from & Other Stories. Style with leather knee-high boots and tights. This outfit is simple to throw together—a tailored wool coat adds a polished feel—and even easier to shimmy out of and into pajamas once you're back home.

Shop the pieces: 1. & Other Stories dress, $119; 2. Max Mara wool coat, $3,890; 3. Tory Burch handbag, $528; 4. Loeffler Randall boot, $695; 5. H&M black tights, $10

Friday Night Concerts and Shows
Clothing, Outerwear, Jacket, Footwear, Hood, Sleeve, Shoe, Hoodie, Trousers, Coat,
Design by Morgan McMullen

My number one concern at concerts or shows where you have to stand is having my field of vision cut off by a tall person in front of me. Hence, I swear by heeled combat boots, which give off a cool don't-get-in-my-bubble vibe and look fashionable. You can't go wrong with a sexy black bodysuit like this one from Alix NYC and a fanny pack, so you can keep your hands free for drinks or to hold your partner's hand as you guys sway to the music.

Shop the pieces: 1. Alix NYC top, $165; 2. The Arrivals puffer jacket, $395; 3. Everlane black jeans, $68; 4. Longchamp fanny pack, $185; 5. Louis Vuitton ankle boots, $1,420

Exploring Museums
Clothing, White, Jeans, Denim, Fashion, Trousers, Textile, Sleeve, Fashion illustration, Pocket,
Design by Morgan McMullen

The soft colors on this translucent Chloé top reminds me of the hues used in impressionism art. If you see what I see, you'll get why it works as an option for the museum. Paired with mom jeans and sneakers, since you'll be walking around a lot, the look is dressy but not too over-the-top, since you mingle with guests. Most museums have coat check, but just in case you don't feel like waiting in line, choose a lightweight coat you won't mind carrying on your arm. This bomber-style shearling number will keep you warm and isn't heavy.

Shop the pieces: 1. Chloé shirt, $1,850; 2. BLANKNYC jacket, $138; 3. H&M mom jeans, $30; 4. Staud handbag, $325; 5. Golden Goose sneakers, $411

A Weekend on the Slopes
Clothing, White, Black, Footwear, Fashion, Outerwear, Dress, Sportswear, Sleeve, Shoe,
Design by Morgan McMullen

Looking for outdoorsy activities to do with bae? Snowboarding, skiing, and iceskating check off some basic wintertime date ideas. This outfit works for all three scenarios, but especially when you're on the slopes. It's important to be armed with the right waterproof pieces, from your jacket and inner layer (I love this jumper) to your accessories. This water-resistant fanny pack from Hunter will keep all your valuables safe while the Sorel boots keep your feet toasty in the snow.

Shop the pieces: 1. Banana Republic turtleneck, $47; 2. Bogner jacket, $1,450; 3. Kate Spade New York beanie, $58; 4. Perfect Moment pants, $680; 5. Hunter fanny pack, $60; 6. Sorel boots, $170

Sunday Afternoon at the Movies
Clothing, Footwear, Fashion, Outerwear, Headgear, Design, Boot, Shoe, Jeans, Cap,
Design by Morgan McMullen

The two places you won't find me in jeans are on the airplane and at the movies. (I like to be comfortable while gorging on buttery popcorn and Sour Patch Kids.) An alternative bottom I always turn to is leather leggings, which feel like a step up from sweatpants, paired with a cute sweater and easy-to-slip-off-boots. Since you'll be sitting or reclining for at least two hours, you might as well feel like you're wearing pajamas at home. This ensemble even works for a post-movie dinner at your favorite neighborhood restaurant or a stroll through the park.

Shop the pieces: 1. Rails sweater, $248; 2. Nanushka houndstooth jacket, $697; 3. Zara beanie, $20; 4. Spanx leggings, $128; 5. Chloé bag, $1,450; 6. Koio boots, $348

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