Updating your fall boot selection is hard work. After all, these (often leather) numbers usually require a serious monetary commitment. And when we shell out the big bucks, we expect style, comfort and durability in return. In a perfect world, all boots would be as timeless as that moment when we glance at their price tag.
Of course, we can’t ask fashion’s fickle palate to stop evolving — nor would we want it to. And most boots, unfortunately, don’t come heeled with warranties. When it comes to comfort, however, there is an easy way of weeding out the less-than-cozy contenders: Skip the heels.
Even without literally upping your flat boots’ sex appeal, you’ve still got a ton of shapes, styles and fabrics to choose from — all of which look pretty damn good regardless of height. Take the first step (if you will) toward a chic yet cozy seasonal shoe closet. Click through the slideshow above to shop 25 of the season’s most comfortable and stylish flat boots.
[ Next: The 11 Most Comfortable Heel Brands on the Planet ]
Flat Boots Update October 2017
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Mansur Gavriel
Shearling-Lined Suede Ankle Boots, $595 at Matches Fashion
Known for creating It bags, Mansur Gavriel has now crafted the It flat boot for fall. Featuring navy suede, a rounded toe and shearling lining, these bad boys will take you from the great indoors to outdoors pretty seamlessly.
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Zara
Flat Leather Ankle Boots With Zip, $79.90 at Zara
Think of these black leather boots as a blank canvas. You can use them to cap off a red hot long-sleeve dress or a corduroy suit and even Fair Isle knits. The ring pulls in the back keep things interesting.
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Ann Demeulemeester
Lace-Up Velvet Boots, $648 at Farfetch
Chocolate velvet boots that have cozy and chic all wrapped up. These are our new kick-ass boots to flaunt with everything from jumpsuits to jeans to embroidered jean jackets.
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United Nude
Tommy Lee Mustard, $250 at United Nude
It’s the classic Chelsea boot redefined. Four different materials overlap to produce an eye-catching geometric pattern.
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Mango
Zipped Leather Ankle Boots, $119.99 at Mango
Not only will the seafoam green coloring make these stand out, the textured marbled effect and exposed zippers give these ankle boots the upper hand.
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Anna Baiguera
Zipped Booties, $341 at Farfetch
Zipped booties are a fall must, especially when there’s bright orange trim involved.
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See by Chloe
Leather and Suede Ankle Boots, $395 at Matches Fashion
Hiking boots are normally pretty blah, but that was before See by Chloe got its hands on them. Complete with colorful contrasting panels plus pinkish beige, red and black laces, they’re perfect for trekking through the mountains or an urban jungle.
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Dr. Martens
1460 Smooth, $135 at Dr. Martens
Because you can’t go wrong with (green) combat boots this season. These flat babies are the original boot by the legendary brand, meaning you can be both trendy and old school at the same time.
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Clarks
Desert Boot, $240 at Clarks
Desert boots are showing some real staying power, but we like ours with a kick. The natural vegetable tanned nubuck boots are guaranteed to pep up anything from cuffed jeans to maxi skirts.
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Kenzo
Embroidered Stretch Leather Boots, $425 at Luisa Via Roma
These stretchy slip-ons are amped up with colorful floral embroidery. And they’re about as flat as you can get.
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Pyramides
Over-the-Knee Boots, $178 at Anthropologie
Rust is a prime shade for fall since it coordinates well with all things pumpkin spice. And suede is the fabric of the season.
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Vanessa Wu
Metallic Booties, $158 at Anthropologie
No boot roundup would be complete without some shine. These metallic booties are begging to be teamed with a checked coat.
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BAMS
Beatles Gothic Boots, $253 at Farfetch
The neon Southwestern pattern on these shorties is pretty killer. Wear them with a wrap dress layered over a turtleneck right now and with a shearling jacket once the weather takes a frigid turn.
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Alexander Wang
Iggy Flat Bootie, $595 at Alexander Wang
Think moto boots have to have a heel? Nope. These chain-wrapped black boots prove flat can be hardcore.
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Fred Perry x George Cox
Creeper Boot, $230 at ASOS
Get your creep on with these chunky-soled boots. The oxblood shade makes them a slightly dressier option than traditional hiking boots.
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Toga Pulla
Thigh High Rivet Boots, $830 at Shopbop
Westernwear shows no sign of walking off into the sunset, so make sure you pick up a pair of cowpoke-themed flat boots for fall. The rivet details and statement buckles on this high-flying pair will make for flashy strolls up and down the avenue.
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Tanya Taylor
Nedo Combat Boot, $695 at Moda Operandi
Combat boots with a little personality? We’re definitely on board. That graphic 60s-style floral print has us trippin’ and would pair perfectly with a floral prairie dress or a not-so-traditional blazer and jeans combo.
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Henrik Vibskov
Minime Boots, $278 at Farfetch
A unisex set of flats modeled after conventional oxfords. But with a hefty dose of funk courtesy of its navy, ivory and red color scheme.
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H&M
Chelsea-Style Boots, $34.99 at H&M
Little red boots demand attention and a straight-leg pair of jeans. We’ll leave the wash up to you.
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Karen White
Pearl Boots, $265 at W Concept
Sometimes designers can get carried away with embellishments. That’s why we’re fawning over the subtle pearl accents on these jet black boots. They’re fit for a minimalist who dreams of a little extravagance.
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Zara
Buckled Flat Sock Ankle Boots, $59.90 at Zara
A witch-tastic take on the popular sock boot just in time for Halloween. But these will still be worth stepping out in long after October 31.
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Pyramides
Cobalt Leather Boots, $148 at Anthropologie
While we’ve championed rich shades like chocolate, rust and red, there’s something to be said for a seasonless pair of electric blue boots. These flat boots are accented by golden exposed zippers and will tie in nicely with your Erdem x H&M score come November 2.
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Moncler
Blanche Suede Ankle Boots, $615 at Net-a-Porter
These boots are meant to keep you from slipping on the ice, but they earn extra credit for being super stylish. Dig those striped laces.
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Dr. Martens
Kensington Flora Burgundy Chelsea Boots, $140 at ASOS
Chelsea boots that are cherry? Yes, please. Especially when they’re Dr. Martens and boast an air-cushioned sole.
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MICHAEL Michael Kors
Jamie Flat Over-the-Knee Leather Boot, $225 at Neiman Marcus
Every woman needs a sleek, black over-the-knee boot come fall. This flat boot version will have you standing tall slipped over jeans or peeking out from a midi skirt.
