A trusty combat boot
Dr. Martens 1460 Mono Smooth Leather Lace Up Boots
Dr. Martens are a classic go-to for combat boots. You can opt for the brand’s signature yellow stitching or go a slightly more subtle route with solid black. These may require some time to break in, but they’ll be well worth it.
Rave Review: “I’ve been wanting a pair of these for years and finally treated myself to a pair as a Christmas present. It definitely makes a difference if you treat them with some leather conditioner to soften and protect them before you wear them out. Some thick socks help with the break-in period too. They honestly feel like they are going to last forever.”
A cut-out boot
Steve Madden Alyse Fashion Boot
Show off those ankles in a neutral bootie that has cool slits on both sides.
Rave Review: “Love these boots. Super comfortable and light. Fits very well. Love, love, love!”
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A classic pair
AEYDE Neil Leather Chelsea Boots
Just dropping these timeless black boots here, in case your go-to pair has a few scratches or salt stains on them.
A square-toe boot
Jeffrey Campbell Women’s Sherpal Block Heel Booties
With a stylish toe, funky heel, and wine, bold brown or black hues, these boots are about to become your go-tos.
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A pull-on boot
Aldo Shoes Figtree
A simple pair of pointed pull-on boots are a versatile staple.
A croc-effect boot
Schutz Maryana Crocodile-Embossed Leather Boot
All the street style stars own at least one pair of croc-embossed boots, and you should too. It’s basically an unwritten rule.
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a platform boot
Journee Collection Me Too Zarin Platform Bootie
Platforms are still trending, and in boot form, they’ll give all your fall ensembles a ’70s-inspired twist.
Rave Review: “I have never had a boot that did not hurt my feet–very comfortable!”
a long lug-sole option
Charles & Keith Indra Knee-High Boots in Taupe
Nothing like a pair of lug-sole knee-high boots in autumn. These would look so good with an oversided plaid blazer and a miniskirt.
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A front-zip boot
Steve Madden Jones Chocolate Brown Suede
A silver zipper running down the front gives these ankle boots some added edge. They also come in black and bone, JSYK.
An animal-print pair
Aqua Song Calf Hair Booties
A timeless leopard pair of boots are the perfect addition to any outfit. Treat this as a neutral tone.
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a metallic stunner
JW PEI Riya Metallic Cowboy Boot – Silver
A metallic cowboy boot? Yes, please. If only there was also one in gold! I’d snatch those up in an instant too.
a lug-sole boot
Nordstrom Mia Chelsea Lug Boot in Ivory Birch
The thick, rugged soles are great for traction, and the neutral hue will go with so many fall outfits. They are available in two different colorways, and did I mention they are water-resistant?
Rave Review: “I had tried several Chelsea boots from different companies prior to giving this one ago. These are by far the best and I’m definitely keeping them. They’re really nice quality; I love the stitching and the lug sole. It’s great that they’re water resistant, too. They look more expensive than they actually are and are good quality. I can wear comfortable thicker cotton sock with these with no problem.”
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A heeled ankle boot
Everlane The Short Banana Boot
A sleek boot with a sleek stiletto heel is ideal for those fancier occasions where you might want a dressier style. These come in three more different colorways.
Rave Review: “Search is over! These boots were everything I was looking for—they look as good on as they do in the ad. They are comfortable and a great heel height to still look stylish. Purchase of the year for me!”
A sock boot
everlane The Glove Boot ReKnit
A knit boot like this one has just the amount of stretch you need to keep your foot in place all day long.
Rave Review: “This boot fits like a glove and hugs your feet, giving your ankles support throughout the day. I wore these on day one and two for 12 hours each day. I work in retail and I’m on my feet ALL day on tile flooring (which can be extremely painful at times), but these boots are awesome! I will be ordering another pair.”
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An Ugg Boot
UGG Classic Mini II Genuine Shearling Lined Boot
Ugg boots aren’t going anywhere! This mini version is super comfortable and easy to slip on, whether you’re wearing them around the house or out.
Rave Review: “The mini size is great and much more versatile than the OG size. These are super lightweight and keep my feet comfortable and warm on these cold winter days.”
A harness boot
Frye Veronica Harness Short Boot
Frye knows a thing or two about stylish (yet sturdy!) boots. These timeless harness-trimmed ones have a zipper on the inner ankle, so you can get in and out easily.
Rave Review: “Perfect shoe. I barely had to break them in—they were comfortable the first few wears. I love how they go with every outfit and look. High quality, and true to size.”
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A rain boot
Stutterheim Chelsea Rainwalker
Fall can bring some truly gross, rainy weather. Stay prepared with these cute natural rubber boots, which conform to your foot shape with wear and have heel tabs for ultra-easy on and off. Love to see it.
Rave Review: “Absolutely great footwear. A delight to wear, very fashionable, comfortable, and winter-proof. Highly recommend! This is my second pair. Why two pairs? Because I just love them!”
a suede pair
Larroude Larroude Kate Boot in Brown Suede
For an effortless aesthetic, pair a suede boot (this one by Larroude also comes in ivory, black, caramel, and even Swarovski crystals) with a dress or a top and dark-wash jeans.
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A luxe Chelsea boot
Stuart Weitzman Gotham Zip Bootie
I’m sure you already have at least one ankle boot in your closet. But do you have a pair with this sort of fancy-looking croc texture? Didn’t think so.
Rave Review: “Hard to find elevated shoes that are actually comfortable. These are!”
a cream-colored bootie
Rebecca Allen Women’s The All Weather Boot
These Rebecca Allen boots are perfect to wear all year round. Don’t listen to whoever says you can’t wear white after Labor Day.
Tarah-Lynn Saint-Elien is the fashion editor at Cosmopolitan, writing weighty and witty stories that run the gamut of gushing over Zendaya to convincing you of everything you need in your closet! She began her journey in the industry with a fashion and faith blog and an internship at Elle.com almost 10 years ago. Since then, she’s also served as the style editor at The Haitian Times. The Haitian-American pageant queen is a Syracuse Masters graduate and the author of two books, including: Claim Your Crown. Follow her on Instagram and Twitter: @iamtarahlynn.
Andrea Zendejas is the Senior Accessories Editor at Cosmopolitan, where she has worked for 5+ years. Andrea handles fine and costume jewelry, shoes, and bags for all cover and fashion stories in addition to overseeing the front of book shopping pages. She also styles beauty well stories and various fashion stories for digital. Andrea previously worked at CR Fashion Book, SELF Magazine, and Women’s Health and has contributed to digital sites Harper’s BAZAAR and Marie Claire. Follow her on Instagram.
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