15 of the Best Flat Boots That Combine Fashion and Function (Starting at Just $75)

·6 min read

If the past two years has taught us anything, clothing-wise—besides that wearing the same sweat set on repeat is no longer a fashion faux-pas—it’s that when it comes to dressing yourself, comfort is key. Why strap yourself into an underwire bra when the girls can rest easy in a soft bralette? (Or sans bra altogether?) And trap your legs in jeans when you can WFH in some snuggly loungewear? The logic tracks for shoes, too. Because while we love our trendy flatforms and sky-high heels, nothing quite beats stepping out in a pair of seriously cozy flat boots.

Best of all, there’s no shortage of foot-friendly options out there that will be kind to your soles and forgiving to your arches. From equestrian-style booties to over-the-knee showstoppers, here are 15 of the best flat boots you should add to your collection ASAP.


1. Madewell The Citywalk Lug-Sole Lace-Up Boot

Best Lace-Up Boots

“These are my go-to boots,” writes one reviewer. “I love the zipper in the back, and they’re way comfier than they look. I pair them with a cute printed sock that peep over the edge.” Sounds like a bit of fashion advice we’ll definitely be taking.

Buy it ($295; $177)

2. Sam Edelman Lenley Combat Boot

Best Combat Boots

Combat boots are once again trending, and we aren’t mad about it. We particularly like the uneven topline on these bad boys and the silver hardware that give them just the *right* touch of rocker-edginess that we’re looking for.

Buy it ($200; $140)

3. Hunter Original Refined Creeper Boot

Best Creeper Boots

Stretchy neoprene that conforms to your ankle and a cushioned footbed gives these creepers a walking-on-a-cloud sort of feel.

Buy it ($160)

4. Everlane The Rain Boot

Best Weather-Resistant Boots

Sure, it may be raining cats and dogs outside, but that doesn’t mean your sense of style has to suffer. These rainboots are equipped with a slip-resistant tread, stretch panels and a cushioned insole for a cozy fit that leaves just enough wiggle room for your thickest pairs of socks. Oh, and they’re pretty cute, too.

Buy it ($75)

5. Naturalizer Rena Boot

Best Knee-High Boots

Does the supple leather and equestrian-inspired vibe of these knee-highs make anyone else want to slip on their warmest cable-knit sweater to go peruse the book stacks at the library? Just us?

Buy it ($240; $190)

6. Aquatalia Maddie Calf Ankle Leather Booties

Best Splurge-Worthy Boots

Yes, these are definitely a splurge, but after one walk in these timeless—and ridiculously comfortable—ankle boots, you’ll see why Aquatalia is one of Meghan Markle’s favorite shoe brands.

Buy it ($495)

7. Camper Pix Ankle Boots

Best Ankle Boots

This is one of those styles that feels simultaneously modern and timeless. We especially love that the durable outsoles are waterproof and that the insoles are crafted with Ortholite for an extra-soft fit.

Buy it ($199; $159)

8. Sarto by Franco Sarto Fera Over the Knee Boot

Best Over-the-Knee Boots

Stretch material over-the-knee boots can be a bit intimidating due to their fit. But if you’re worried that these will feel a bit too suffocating on your legs, never fear. “I was really nervous to order these, as I have really large thighs and boots rarely fit me properly,” one reviewer notes. “These did not disappoint! They look and feel great.”

Buy it ($170; $120)

9. Silent P Piah Chelsea Boots

Best Rubber-Toed Boots

Another footwear trend we aren’t disappointed is making the rounds? Lug-sole boots. And this pair delivers that cool, street-style factor thanks to the chunky soles and rubber bumper (which is also great for protecting your toes during your daily subway commute).

Buy it ($140; $84)

10. Tory Burch Runway Buckle Boot

Best Riding Boots

Circling back to equestrian-style footwear, these riding boots are definitely statement-makers, but easily pair with just about everything that’s currently hanging in your closet. “I love these riding boots,” writes a five-star reviewer. “They’re chic yet comfortable and so versatile and stylish. They look great with a midi length dress, black leggings or a long sleeve tunic.”

Buy it ($558)

11. Staud Palamino Chelsea Boot

Best Pull-On Boots

Sometimes you want a pair of boots that you can pull on and walk out the door—a no-fuss kind of shoe, if you will. If that’s the case, then these will become your go-tos. It’s important to note that this style comes only in whole sizes, so if you typically order shoes in a half size, your best bet is to size up.

Buy it ($375)

12. Everlane the Italian Leather Chelsea Boot

Best Chelsea Boots

Combining style with functionality, these best-sellers pair well with your most casual get-ups, but can easily be dressed up if the occasion arises. Plus, they come in a variety of neutral tones, so you’ll find one that fits your vibe whether or not you’re hoping to mix things up and stray from the usual black.

Buy it ($195)

13. Cole Haan Zeogrand Luxe Hiker Cold Weather Boots

Best Winter Boots

Winter weather is here, and the time to keep your footsies toasty warm is now. These water-resistant booties with a faux-shearling lining will do just the trick. As one reviewer says, “These are the most comfortable boots ever. The tongue is so soft and wraps around the entire front of your leg and ankle. I don’t want to take them off.” Sold.

Buy it ($250)

14. André Assous Peggy Faux Shearling Weather Resistant Chelsea Boot

Best Fur-Lined Boots

Speaking of winter appropriate footwear, if you’re hoping to snag a more understated design this season, we recommend these puppies. But don’t just take our word for it. “I have been searching endlessly for the perfect winter Chelsea boot and these are it,” one reviewer writes. “The shearling inside makes them the most comfortable boot I’ve ever owned, so warm and soft, and the fact that they’re waterproof is a huge plus. They feel really durable but also look expensive and stylish.”

Buy it ($239; $143)

15. Matisse Margot Leather Boot

Best Zip-Up Boots

We love a good utilitarian boot, and are particularly sold on this zip-up pair from Matisse. The thicker sole gives your feet some extra support, and the soft leather molds to your ankles for a true-to-size fit.

Buy it ($118)


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