How To Dress Warm—But Still Cute—When Going On a Winter Date

As much as I love the holiday season and snow days, dressing for winter weather can be a challenge. Most days, my cute outfit ends up hidden by bulky layers and boots in an attempt to stay warm. The other days, I (stupidly) decide to wear what’s cutest rather than what will keep me warm, and I end up regretting it 10 seconds after stepping outside. Sometimes it seems like an impossible task to dress cute and stay warm at the same time. What’s a girl to do? 

As if getting dressed for a date​ isn’t stressful enough already, for the next few months of winter we’ll have to factor weather into our outfit decisions as well as style. For a winter date, the old me would most likely choose to dress cute instead of warm, and I’d end up freezing my butt off. But for the new year, I’ve decided to turn over a new leaf and find the right balance of cute and warm.  Lucky for you, I’ve rounded up some of the my best winter date styling tips that’ll keep you looking just as cute as you are cozy.  


  1. 1. Throw on a statement coat

    If you’re all about bold fashion and making a statement, make your coat the star of the show. Rather than your basic black puffer, go for a fun, trendy coat that will elevate your outfit rather than hide it. Fur, sherpa, or leather are great options that will look good and keep you warm. 

    Fashon blogger Katie Sands paired her fur coat with all black underneath so that the coat was the focal point of the outfit.  You can recreate her look with this faux fur coat from Kohl’s, ($98; shop now) these jeans ($25; shop now) and these killer boots ($135; shop now). 

  2. 2. Embrace the sweater weather 

    If you’re going on a casual date, there’s no need to spend hours concocting the perfect look. Just tuck a ​cute sweater ​into jeans and you have the perfect “I didn’t try too hard but still look good” look that every girl wants.

    I love the button details on blogger Rachel Martino’s sweater. Bonus: you can layer a long sleeve tee underneath your sweater for extra warmth and no one will know.  Steal Rachel’s cute and cozy aesthetic with this wrap sweater from Abercrombie ($68; shop now).

  3. 3. Elevate your basics

    Amp up your basics by opting for renditions of simple pieces in fun fabrics. Puffer coats are being revamped in luxe velvets and cozy sherpas this season, so be sure to pick one up to put a more fashion-y twist on your everyday staple. I am obsessed with sherpa puffer from Abercrombie ($160; shop now

    One of my favorite pieces for winter weather is leather leggings. They look so chic with a touch of badass style. Pair yours with a sweater and take your everyday uniform up a notch. Pick up a pair of these vegan leather leggings from Express ($50, shop now) and automatically take your winter looks from girl-next-door to fashion blogger. 

  4. 4. Make tights your new BFF

    When that brand new skirt is calling your name, layer on a pair of tights to keep your legs warm. Basic black ones will go with just about everything in your closet. It may not seem like that sheer layer of fabric will make much difference, but trust me: it makes a difference.  Stock up on these ones from Urban Outfitters ($5; shop now).

  5. 5. Stay bundled in cozy accessories

    For an outdoor winter date - think ice skating, sightseeing, sledding - opt for cozy accessories like hats, scarves, and gloves. Steer towards colors that go with the rest of your outfit so they look like a conscious choice rather than an afterthought. Neutrals are always a good idea!

    This cozy blush hat ($1; shop now) matches Lauren Conrad’s sweater perfectly.  Pair yours with a knit scarf ($10; shop now) and some fuzzy gloves ($18; shop now) for maximum coziness.

  6. 6. Rock some long hemlines

    For all you die-hard dress wearers out there (myself included), stick to longer hemlines this season in thicker fabrics, like velvet. Luckily, longer skirts and dresses are trending right now, so you’ll have plenty of options when searching for long hemlines.  

    This checked skirt from Topshop ($75; shop now) would look great paired with a black long bodysuit ($29, shop now), a denim jacket ($70; shop now), and black booties ($50; shop now). 

Plummeting temperature doesn’t have to mean your style plummets as well. Choosing flirty looks that will still keep you warm may seem like a tall order, but with these basic adjustments, you’ll be ready to take on any winter date. 

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