The 6 Rules of Wearing Winter Boots in 2023

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Winter boots aren’t exactly the most stylish footwear option, but once that snow starts coming down and sidewalks turn into a maze of ice and slush, you’ll be glad you reached for your trusty lug-sole Sorels rather than your sleek new leather booties. But just because the weather calls for practical footwear doesn’t mean you have to forgo style all together. Here are the six rules for making winter boots look fashionable and cool in 2023.

11 of the Best Winter Coats for Short Women (Because No One Wants to Look Like a Marshmallow)

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1. Stick with Leggings or Skinny Jeans for Easy Tucking

Wide-leg pants and loose denim may be some of the trendiest pant options right now, but one item they don’t play nicely with is winter boots. Leggings, skinny jeans or other slim-fit pants will fit much more smoothly into the shaft of your boot and create a nice lean line that elongates your legs.

Shop similar styles: Madewell Larsen Double-Breasted Blazer ($188); Quince Mongolian Cashmere Turtleneck Sweater ($80); Zella Live In HIgh-Waist Leggings ($59); Tory Burch Lee Radziwill Small Double Bag ($998); Sorel Brex Boots ($180)

2. Or Choose a Cropped Pant That Hits the Top of Your Boot

If you really can’t give up on your beloved straight-leg jeans (or you’re part of the “death to skinny jeans” movement), opt for pairs that hit right at the top of your boot like Coterie member Tyla-Lauren Gilmore. Then you won’t have to deal with trying to stuff all that extra fabric into your socks, nor will you have to worry about the hem of your jeans getting snowy or dirty if they’re layered over the top. (P.S. This works best with boots that are ankle height rather than mid-calf or higher. A taller boot plus super cropped jeans will throw off your proportions too much.)

Shop similar styles:Nordstrom Recycled Cashmere Blend Beanie Hat ($44); ASOS Faux-Fur Coat ($171); Agolde Pinch-Wait High-Rise Kick Jeans ($188); The North Face Chilkat V 400 Waterproof Boots ($159)

3. Make Super Practical Boots Look Chic by Repeating Colors

Let’s be honest, the best winter boots are frequently the least stylish (not always, but often). So how do you make sturdy, rubber-soled, lace-up boots look cute enough for meeting up with friends? Take inspiration from Grace Atwood and repeat the colors of your boot elsewhere in your outfit. Her chic beige jacket and chocolate cashmere turtleneck perfectly complement her tough winter booties and help to elevate the look overall.

Shop similar styles: Buck Mason Baja Twill Field Shirt Jacket ($128); GAP MerinoTurtleneck ($70); Abercrombie & Fitch High-Waist Skinny Jeans ($89); Cuyana Mini Double Loop Bag ($228); UGG Adirondack III Waterproof Boots ($250)

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4. Lean Into the Rugged Vibes with Cabincore Staples

Winter boots will always have something of an outdoorsy, sporty vibe, so why not lean into it with other cabincore styles? Rather than trying to make your boots into something they’re not (sleek, pointy-toe leather shoes that pair beautifully with shirtdresses and blazers), embrace their ruggedness with flannel, shackets, denim and wide-brim felt ranchers.

Shop similar styles: Blank NYC Plaid Shacket Coat ($158); Sheertex Classic Sher Rip-Resist Tights ($59); Kamik Ariel F Winter Boots ($140)

winter boots style rules boots with dresses
Michael Campanella/Getty Images

5. If You Plan to Wear Dresses or Skirts, Stick with Black Boots

Black boots plus black tights will make your legs look long and lean, even if said boots are chunky, as most winter boots tend to be. Opt for a style that is all black—upper, sole, shearling, shoelaces, etc.—to really play up that leg-lengthening effect.

Shop similar styles: Everlane ReNew Long Liner Coat ($198); Boden Chunky Fair Isle Cardigan Sweater ($190); J.Crew Gwyneth Slip Skirt ($90); Spanx Tight-End Sheer Tights ($28); Sorel Lennox Lace Cozy STKD Waterproof Boots ($210)

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6. Leave the Moonboots in the ‘60s

Super puffy moonboots and chunky UGGs are not the way to go if you’re prioritizing style. No matter what, they end up looking comical or like a costume (which is fine if that’s what you’re going for), but lace-up styles and slimmer fits will always look much more chic and are every bit as warm and cozy.



Abby Hepworth is an RRCA-certified running coach who has worked in fashion for over 10 years. Want to know what shoes are in this season? She's got you. Need recommendations on...