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

PureWow editors select every item that appears on this page, and the company may earn compensation through affiliate links within the story. All prices are accurate upon date of publish. You can learn more about the affiliate process here.

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.


madewell flat boots

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.

sam edelman combat boots

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.

hunter creeper boots

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.

everlane rain boots

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.

black knee high boots

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?

aquatalita ankle boots
Saks Fifth Avenue

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.

camper ankle boots

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.

franco sarto over the knee boots

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.”

piah d chelsea boots

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).

tory burch knee high boots
Tory Burch

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.”

staud boots

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.

everlane chelsea boots

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.

sorel winter boots
Saks Fifth Avenue

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.

andre assous fur lined boots

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.”

zip up leather boots

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.

purewow author
Anna Smutny

Commerce Editor

Anna Smutny covered a range of beats, from fashion and beauty verticals to home decor (and everything else in between) for PureWow from 2021-2022. With a background in wedding and...
read full bio