If having a baby or chasing a toddler didn't break you of your heels habit, chances are a global pandemic may have. Just as we've transitioned to more comfortable bras, the thought of cramming our feet back into foot hobbling heels sounds like absolute torture.

Most days my go-to is a slip-on sneaker (laces are also too much work anymore) but sometimes you need something that packs the sass and style of a heel. Enter: Comfortable flats.

The right pair of flats can pair with anything from joggers or jeans to pleated skirts and sweater dresses. They're versatile and often timeless which makes some styles great investment pieces. However, they're not all created equal. I've owned more than my share that have chewed up my heels or rubbed all the skin off my poor little pinky toe. I've limped into drug stores in various world cities looking for blister bandages despite thinking I'd packed properly. This is to say, I've learned from my mistakes and now know how to evaluate what makes a pair of comfortable flats. Let me help you, too.

From the best pointy-toed flats to ballet flats and even gorgeous loafers that convert into mules, there's something here for every (practical) fashionista.

Our favorite comfortable flats

OSAY flats

OSAY

$148

Loafer Flats

Can’t decide between a slip on or a loafer? With the signature heel-folding style from sustainable geniuses O S A Y the label, you don’t have to. Even better? They’re handmade in small batches of recycled cowhide and leather that’s so supple it molds right to your foot.

Rothy's The Point

Rothy's

$145

The Point

If your heels wearing days are on hold (or you’ve just embraced the flats lifestyle) you need a pair of Rothy’s in your closet. (Chances are good you already do. They’re practically synonymous with flats at this point–and for good reason!) They’re comfortable, go with everything and are totally machine washable. It’s always hard to pick a color, but this season’s Dragon fruit hue brings is super on-trend given its undeniable Barbie-core vibe.

Rothy's The Driver

Rothy's

$185

The Driver

Sorry, too hard to pick just one Rothy’s option. This particular style, with its classic silhouette, cushiony insole and grippy nubbed outsole, is the perfect shoe for dashing from the office to soccer practice and (if I’m lucky) right into date night. Are they pricey? Quite. Do they always look brand spankin’ new even when you wear them every single day? Sure do. (Disclaimer that these seem to run a bit smaller than the above style, so you may need to size up to prevent the heel from rubbing.)

M.Gemi Felize Shearling Mule

M.Gemi

$248

Felize Shearling Mule

Beat it, UGGS. Gorgeous handmade Italian mules that are also lined with shearling? Be still my heart. Made by female artisans, they’re the perfect intersection of comfort and class with a crocodile embossed leather, moldable footbeds and durable Gommini soles. They’re absolutely perfect for fall!

Allbirds Tree Breezers

Allbirds

$100

Tree Breezers

From the minute we discovered their Tree Runners, we’ve been Allbirds super fans. Similarly to their ultra-comfy sustainable sneakers, the Tree Breezers are lightweight and breathable and completely machine-washable. They’re the perfect shoe to throw in your bag for commuting but stylish enough you don’t have to change into heels if you don’t want to. Choose from a ton of fun colors or stick to the neutrals if that’s more your style.

Birdies The Goldfinch

Birdies

$130

The Goldfinch

A pointy toed flat you could wear to literally everything from PTO meetings to weddings? You got it. The endless possibilities have us totally swooning over these supple gold leather numbers from Birdies. And while we’d suffer through discomfort to wear something so pretty, we totally don’t have to. The seven-layer footbed and no-slip rubber sole make them feel like little golden clouds.

Toms Jade Flat

TOMS

$89.95

Jade Flat

We’ve never met a pair of TOMS we didn’t like. Their OG slip ons are a perennial staple in our summer shoe line up and their more sophisticated styles are a home run as well. This fall we’re feeling the Jade with its slip on style and leather upper which looks perfect with cuffed jeans.

Everlane Italian Leather Day Glove Flats

Everlane

$115

Italian Leather Day Glove Flats

With over 6K reviews, the Day Glove from Everlane seems to have become one of their most beloved staples. The practical but still fresh style is designed in supple Italian leather to literally fit like a glove. (It may take some breaking in, but it’s so worth it!) Side vents and a grippy rubber sole make them perfect for go, go, going all day long whether you’re embarking on a European adventure or just running to pick up.

[This was originally published August, 2018. It has since been updated.]