The Most Comfortable Flats EVER! (2020)

 

Comfy Flats

Living in New York City, I walk for miles every day and have gradually stopped wearing heels altogether. There's nothing worse than new heels stuck in subway grates or your shoe sliding off your foot while you sprint to cross the street before the light turns.

So instead, I wear flats.

Classic ballet flats for work, cute embellished flats for drinks and dinner, or casual loafer flats for weekend errands – I even pack soft leather flats for travel! After trying so many brands over the years (both designer and orthopedic), I've finally found a couple tried and true brands that make chic, comfortable flats the best option there is!

So, if you're also looking for comfy flats that will support your feet while still coordinating with your wardrobe – keep reading!

 

 

The Most Comfortable Flats

There are a couple brands in particular that focus on comfortable flats. Below, we've chosen our favorite styles that are both comfortable and stylish!

 

 

Keep reading for reviews of each, or pin this article to save it for later ⇟ 

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Most Comfortable Flats
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Best Flats 2020

 

Everlane Flats

Everlane is my go to for high quality basics that last – and their shoes are no different. With several different styles made from buttery soft 100% Italian leather, it's easy to see why Everlane shoes are a cult favorite. 

If you hate toe cleavage, opt for these flats. They truly fit like a glove and mold to your feet over time for that perfect fit.

If you prefer a slimmer look, this flat is sleek and comfortable all day long. It's a great flat to wear to work and can withstand long commutes – and even longer meetings!

Plus, all of Everlane's flats come in a huge range of colors so you're bound to find the perfect option for your style. For more of my favorites from the brand, check out my Everlane review here.

Everlane Flats

Sold on Everlane

Check the latest reviews and see all color options here.


 

Hush Puppies Flats

Hush Puppies makes an adorable ballet flat that's super comfortable. They're crafted from a breathable suede so your feet don't sweat like crazy and, best of all, they're incredibly affordable. To break them in, I bend the shoe a bit back and forth, and from side to side, to give them some additional stretch and flexibility.

Other things I like about Hush Puppies' flats: the leather is soft and squishy, so they pack down tightly for travel. I also like how the rounded toe doesn't show any toe cleavage and provides enough room for your toes to sit comfortably as you walk.

Best of all, Hush Puppies keeps this flat in their staple shoe line up and offers a huge range of colors, so you can definitely find a shade you like.

 



 

Birdies Flats

Birdies flats are truly as comfortable as they say.

The cheetah calf hair Starling flats are my go to whenever I need to run errands or walk miles. Thanks to a cushy memory foam interior and non slip rubber sole, these flats can withstand miles of concrete pavement and, a year later, still look brand new.

While they are a little pricier, Birdies is one of the few brands that nails both comfort and style. In fact, I have multiple pairs from the brand because they really do offer all day comfort.

Don't just take it from us – even Meghan Markle loves them!

Birdies Flats

Sold on Birdies & Nordstrom

Check the latest reviews and see all color options here.


 

Tory Burch Travel Flats

With over 1,000+ reviews, it's safe to say it's not just me that loves the Tory Burch travel flats! The leather is incredibly soft, the fit is quite comfortable, and these flats work great as a driving shoe or walking shoe.

I've worn them as part of my casual airport outfit with stretchy jeans and a jacket as well as part of my everyday work uniform with a blouse and skirt. I order my usual size, give them about a day to break in, and over time they mold to perfectly cushion my feet.

The best part is Tory Burch makes them in a rainbow of colors and finishes. I particularly like this blush pink ballet flat with the subtle matching pink Tory logo, although there are gold and silver hardware finishes if you prefer more of a statement!

Each pair is very well made, so they'll last you a good couple years.

 



 

Nine West Ballerina Flats

These Nine West flats are really cute.

They're perfect if you're looking for a classic ballet flat, and I've picked them up in a variety of colors – the black flats especially are very work appropriate with a suit.

If you struggle to find comfortable, stylish flats for work, definitely take a closer look at these Nine West ballet flats. I would also recommend sizing down a half-size as they run slightly big.

Or, you can go with your normal size and add gel inserts for added cushion!


 

Frye Flats

The Frye flats are a cult favorite. Comfortable right out of the box, they're versatile enough to match any outfit and durable enough to last miles of walking.

Frye uses super-soft antiqued leather for all its shoes, and these ballet flats are no exception! You can get them in pastel suedes, neutrals or metallic finishes.

The only downside to the Frye flats is the bottoms are really smooth, so you can slip occasionally if you're a fast walker (or klutz) like I am. Just add shoe pads for some grip, and it's not a problem!

 



 

Vionic Flats

Vionic flats are perfect if you have plantar fasciitis.

They're an Australian orthopedic brand dedicated specifically to help those with foot pain, and they even partner with a podiatrist to develop bio-mechanical foot beds in all its shoes. These foot beds provide significant pain relief and arch support.

The effect of all that built-in padding is a cushioned hug for your arches that makes walking on concrete feel natural.

Especially if you have flat feet, you'll be surprised at how Vionic shoes enable you to walk comfortably! I also think they look sharp enough to wear to work, which I can't always say for orthopedic shoes!


 

Skechers Flats

These Skechers are soft, flexible and comfy. Made from a fabric upper, these affordable shoes offer limited stretch, so make sure to buy your regular size! 

If you have bunions, you should definitely give these a go! My mom owns several pairs of Skechers as they hide her bunions quite well while still being comfortable enough for everyday wear.

Skechers makes these flats in a range of muted colors and I like the minimalist, logo-free look.

 



 

Clarks Flats

Clarks are a go-to for extremely comfortable shoes.

Their cushioned flats are no different, and with tons of styles to choose from, you can find both classic black flats for work and more stylish colorful flats for travel!


 

Trotters Loafers

Comfortable pointed toe flats can be hard to find. Inevitably, the cute ones squish your toes in the front!

Once I discovered Trotters, I was hooked.

These give a really nice menswear vibe to my girlier outfits while still being polished enough to wear to work. I usually pair them with a blouse and ankle pants, and the pointy toe helps make your legs look longer.

I find these loafers super comfortable to wear, even for long periods, as they've got some padding in the insole. They come in black, off white, pink, suede and printed versions.

I also really love these woven flats and think they'd look perfect in the summer!

 



 

French Sole Ballet Flats

 

I'm a huge fan of French Sole.

They make really high-quality ballerina flats as part of their core shoe line, with some embellished versions each season if you want something unique. 

The ‘Jigsaw' is a beautiful scalloped shoe that looks very similar to the designer flats Chloe makes (but obviously much more affordable!) and the leather is unbelievably soft – no painful digging into your feet!

It features a rounded toe, so no foot cleavage – thank goodness – and a slight heel just high enough to make you feel like you're not barefoot on the ground. I'd say the foot bed support is light to medium.

In general, French Sole works best for narrow feet. These are available in a huge range of colors – both suede and leather!


 

Naturalizer Flats

If you want a comfortable flat for work, consider these Naturalizers, which come in a wide range of neutral shades and have a fun buckle on the front.

They look much more expensive than they are! The footpad is slightly padded and they're a chic, sophisticated flat to match any suit or wide legged trousers.

Naturalizer also makes this loafer that has lots of padding and contoured foot support if you want a menswear-inspired flat!

 



 

Coach Classic Flats

I typically try to buy shoes made of real leather, since they're better for your feet.

If you want gorgeous leather or suede shoes, Coach is the brand to beat! These classic ballet flats are simple yet stunning, and I love them equally in black or the dusty pink.

The footbed is lightly padded, the heel doesn't slip off your foot and the micro heel raises them slightly off the ground. I knew when I got these that the classic shape wouldn't go out of style, and they've held up well for years!

Size down a half-size for the best fit!


 

Sam Edelman Flats

Sam Edelman is one of my go-to shoe brands since they make cute, comfortable shoes that look like more expensive designers at a very affordable price point.

Case in point: these classic flats are a great dupe for the Chloe Lauren flats…at less than a fifth of the price.

They have a classic look, with a scalloped edge that works equally well in the office as a work flat as they do on the weekend when worn to brunch with a tee and jeans.

I never get blisters on my heels when I wear these (even if I wear them all day!), and the foot bed is lightly padded. Sam Edelman makes these comfy flats in a couple different neutral colors as well as in both suede and leather.

Best of all? There's no toe cleavage!

 



 

UGG Flats

These UGG loafers feel like wearing clouds on your feet. They're super comfortable, have fantastic arch support, and are great quality!

I wear UGG slippers around the house and most days, transition into these out the door… so it feels like I'm still wearing my slippers to work! UGG says they're made with triple layer foam cushioning to provide that extra support and comfort.

I love the classic metallic flats to add a pop of color to outfits, but you could opt for the black or nude for a more conservative, neutral look. Usually, I have to size up for UGGs.


 

Everlane Slingback Flats

If you're a fan of Everlane shoes and especially the classic Editor heel, you are gonna love the Everlane Editor Slingback.

Made with Italian leather (and no, this is not one of those “assembled in New Jersey” deals, they are actually made in Lastra a Signa, Italy. Very classy!), these versatile and comfortable flats can work equally great with business formal wear or as a smart accent to your Friday night outfit.

Bear in mind the Editor Slingback runs a bit narrow, and Everlane recommends sizing a half-size up!   

 



 

VenusCelia Flat Loafer

The real reason the VenusCelia loafer is among the most comfortable flats ever is because – like so many of life's great wonders – this shoe is just so much more than meets the eye!

The rubber sole provides the grip of a topsider, the memory foam insole offers the comfort of a slipper, and the metal ornament adds that touch of Tory Burch class! 

Another great thing about these comfy flats? They come in more colors (30) than dollars they cost! How about that??

 



 

The Best Flats 2020- Summary

To summarize, here are our favorite brands for comfortable flats!

 

 



 

What to Look for in Comfortable Shoes

While it can be relatively easy to find comfy sneakers these days, chic flats are a little tougher. To help, I stock up on memory foam shoe inserts, heel cushions and heel liners! There's a couple elements you want to look for to find the perfect flat:

  1. Adequate Sole Support
  2. Breathable Fabric
  3. A Roomy Toe Box

Not all flats are created equal. Finding comfortable shoes that don't pinch, squeeze, rub or create blisters can feel impossible. I walk a lot on concrete pavement in New York, so I prefer insoles with a bit more support to cushion and absorb the shock. Bonus points if they're molded for arch support!

If you fall in love with a pair of pretty flats that don't have built-in support, you can try sizing up a half-size and adding shoe inserts and cushions to beef up that comfort!

I also try to stick to high-quality leather or suede shoes without fabric uppers so that my feet can breathe. There's nothing worse than stinky feet, and usually the culprit is poor-quality shoes. To make my suede shoes last longer, I spray them with this protector when they're straight out of the box!

And finally, for all-day comfortable flats I usually opt for a rounded toe. I find these offer more room for my toes to spread out while I'm walking. Hope these tips help! What are your tips for finding great flats?

 

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[…] There’s always some variation of them each season (love the two toned color) and these double as a great work flat. […]

[…] example, if you’ll be in a rainy area with lots of puddles, you’ll want to invest in waterproof flats with a rubber sole to keep your feet dry. But if the weather’s a bit drier, your options are […]

DeeDecember 24, 2019 - 1:30 am

Over the last few years I’ve tried flats but I ended up with blisters or they were very uncomfortable and I’d return them. I really feel in love with the cute little bow on the Nine West ballerina flats. I searched all the websites before finally giving up. I can’t find those shoes in black in a 8 1/2 or 9. Nine is my normal size but your article advised to go down half a size. Can you please help me.
Dee

SherDecember 28, 2019 - 3:34 pm

Hi Dee, unfortunately it looks like they’ve sold out.

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