When the cold weather comes around, it can be easy to go out and shop for the first black boot you see. But when it comes to narrowing it down to the best option on the market, it can be difficult. You're left with hundreds of options, and you may even leave a site more confused than when you first started shopping. In an effort to find the boots of the season, I reached out to the experts, Net-a-Porter's senior fashion market editor Libby Page and Shopbop's fashion director Caroline Maguire. Since it's their jobs to pinpoint the fashion direction of the most popular retailers (that we love here at WWW) I knew they'd deliver a slew of good picks.
Ahead, you'll find the black ankle boots they think are the best of the season. They know exactly what their customers want and need, so If you're shopping for a staple black ankle boot, the options below will be sure to stay with you for a long time. Keep scrolling to uncover your perfect pair—and complete your winter wardrobe once and for all.
Shopbop
"Dr. Martens check the boxes of both style and comfort. The platform sole and cozy faux fur lining are sure to keep you warm as you venture out into the cold!"
"Our customer loves the lug sole Chelsea boot this season, it’s a boot that everyone can pull off! These Chelsea boots are a great pull-on option when you just can’t be bothered with laces."
"These boots are perfect to give your look (and height!) a little boost."
"The rubber trim paired with a platform sole is sure to make a statement wherever you go. It's a bold look that is both on-trend and practical!"
"The white stitching and pull tabs add a feminine flair to these lace-less lug boots, making an effortless look that’s both versatile and chic."
Net-a-Porter
"Comfort is key this season, so I’ve opted for flat boots from the most dominant trend we’ve seen in the market, the ‘Chunky Chelsea’."—Page
"The rubber sole here is great and adds a practical nature."
"For the days where I want to add a little sharpness to my outfit, Bottega Veneta and Khaite smarten up any look."
"The sleekest lace-up combat boot."
Shop More Black Ankle Boots:
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Forget What You've Heard—Ankle Boots Are Still In, and This Expensive-Looking (But Just $50) Pair Is ProofGrab them before they're gone.
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This "Ugly" Shoe Trend Is Officially Back From 2016—But This Time, It's BetterSpotted in London and NYC.
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This Is the 2025 Way to Wear the Ankle Boot Trend Everyone Bought 4 Years AgoPSA: Don't toss them yet!
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Forget Flats—Everyone With Good Taste Is Wearing These Boots With Jeans and a JacketPut these on your shopping list.
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Just a Reminder: *This* Is the Best Pant Style to Wear With Every Type of BootThey're model-off-duty approved.
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Not Skinny, Not Wide-Leg—J.Lo Just Wore Ankle Boots With 2025's Most-Wanted Pant TrendCopy this fall outfit ASAP.
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New Yorkers Will Wear This Celeb-Concocted Ankle-Boot Outfit for the Next 3 MonthsSydney Sweeney just modeled it for us.
