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6 Winter Date Night Outfits That Are So Easy to Copy

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Getting dressed for a date night when temperatures drop can be just as daunting as the date itself (especially if it’s a first date). Cue the internal monologue, Are these heels overkill? Do these jeans make me look underdressed? However, with little help from our guide below, you’ll be good to go in no time. As for the date itself, well…that one is on you (with a little help from us, of course). From a classic leather jacket to a pop-of-color knit dress, read on for six winter date night outfits that can withstand ultra-low temps and are just as cozy as they are sophisticated.

10 Stylish Winter Skirts to Give Your Overworked Jeans a Break (Plus How to Wear Them)


Winter date night ideas Wear Head-to-Toe Black
Edward Berthelot / Getty Images

1. Wear Head-to-Toe Black

It’s date night—what better time than now to break out that LBO (little black outfit)? You can totally overnight rush your Nordstrom last-minute panic picks—we’ve all been there—or you can rummage through your closet to find a gorgeous black midi dress (open back is a plus), lived-in leather jacket and boots for a quick-thinking, classic look. The result is smart, chic and oh-so easy to recreate.

Shop similar styles: Madewell Washed Leather Motorcycle Jacket ($525); Coach Lane Carryall ($550; $275); Shutz Pointed Toe Boot ($238); Charles & Keith Saddle Bag ($76; $64)

Winter date night ideas Show Some Skin in a Mini Skirt
Edward Berthelot / Getty Images

2. Show Some Skin in a Mini Skirt

Cold weather doesn’t have to be the mini skirt’s seasonal coffin. Whether you’re heading to a dinner res or concert hall, there are plenty of ways to pull off this leggy look. The trick is to play with proportions. For instance, stick to knee-high boots that’ll keep your feet toasty and focus the eye on your mile-long legs. And as not to (quite literally) bare it all on the date, we suggest wearing a high-neck sweater and a midi-length leather coat which grazes the top of your boots for a *chef’s kiss* finish. And, of course, there are also tons of tights options, whether you want a barely-there sheer pair or a super-thick opaque.

Shop similar styles: Reformation Knee Boot ($398); COS Knee-High Leather Boot ($390) Abercrombie & Fitch Vegan Leather Coat ($180; $144); Reformation Mini Skirt ($98); Banana Republic Sweater ($120; $70)

Winter date night outfits Rock a Bold Chunky Sweater and Leather Pants
Streetstyleshooters / Getty Images

3. Rock a Bold Chunky Sweater and Leather Pants

When winter rolls around, so does our love affair with leather pants. Add an unexpected touch to this otherwise hard-edged, moto-inspired piece with a chunky turtleneck in a bold color and pair of eye-catching gloves. If you’re looking to push the envelope even further, take note from Grece Ghanem, the style maven pictured above, and lean into tertiary colors—like magenta and teal—when accessorizing to really garner attention.

Shop similar styles: Agolde Recycled Leather Fitted 90s Pant ($348); ALLSAINTS Turtleneck Jumper ($200); Banana Republic Flare-Sleeve Sweater ($150); ALDO Grandsole ($130; $98); Portolano Leather Gloves ($145; $73); H&M 90s Straight Leather Pants ($35)

4. Don a Statement Knit Dress and Wool Coat

Like a kiss goodnight, a statement dress leaves your date wanting more. Sweater dresses are incredibly comfortable, surprisingly sophisticated and subtly sexy thanks to that figure-hugging cling. Drape on your longest wool coat (bonus points if it hits at the same point as your dress) and some platform Dr. Martens or chunky loafers for a dramatic flair.

Shop similar styles: Polène Numéro Dix BAG ($360); Dr. Martens Audrick Platform Boot ($200); Mango Oversize Wool Coat ($170); Something Navy Sweater Dress ($165; $124)

Winter date night outfits Stick to the Basics
Edward Berthelot / Getty Images

5. Stick to the Basics

Sometimes the most timeless date night looks are the ones that require minimal effort. But how do you reach a balance between oversize and fitted? Take inspo from creator Carrole Sagba and simply couple a roomy quilted shacket with straight-leg blue jeans for a polished silhouette. Finish the look with sexy heeled leather boots and a classic baguette bag for the ultimate Carrie Bradshaw touch.

Shop similar styles: Reformation Nari Ankle Boot ($348); Kate Spade Shoulder Bag ($198); Everlane Rigid Way-High Jean ($108; $81); H&M Quilted Shacket ($70); JW PEI Eva Handbag ($60; $46)

Winter date night outfits Combine Trendy Basics
Jeremy Moeller / Getty Images

6. Combine Trendy Basics

The key with this one is to edit (i.e., stick to the basics of each trend). For example, revive your autumnal baggy jeans by wearing them with an oversize faux shearling jacket—the ‘it’ winter outerwear of 2023.  To finish off your look, take a styling cue from our French friends and slip on a wool beret for flair and warmth. Et voilà, you’re ready to throw a few strikes at the bowling alley.

Shop similar styles: Zara Double Faced Jacket ($129); Avec Les Filles Faux Shearling Jacket ($178; $134); Spanx Long Sleeve Turtleneck ($78); Free People Du Jour Beret ($28); Zara Wool Beret ($28)


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