Comfort Shoes: The Ultimate Guide To The Cutest & Most Stylish


Get excited, guys! It’s comfort shoe time! I know, I know…a few of you out there are groaning because for some reason your heart does not go pitter-pat like mine upon hearing words like “cushioned footbed” and “double layered insole featuring shock absorbent foam”.  Can I say these words just one more time? “Shock absorbent foam”…Ahhhhhhhhh.

An interesting thing is happening, though, with comfort shoe brands. The styles are getting cuter and cuter, and definitely heading in the same direction style-wise as their non-comfort focussed counterparts. I mean…I have a whole section this year on slouchy boots and statement heels!

Many of you know the drill by now. I proselytize about comfort shoes, then I create a monster post including my selections of ALL the cutest and most stylish ones out there right now, and then you guys jump in with comments about your own favorite comfortable shoes, and someone asks where I bought the black sweater-jacket above (it’s here), and then I reply to comments saying how much I love you guys for loving comfort shoes, and then we repeat next season. Yay! Also, this time I gave shout outs in the comments noting shoes with wide and narrow sizing — hope that helps.

For all you comfort shoe dislikers (haters feels like such a strong word)… it’s all good. I won’t be offended if this post isn’t for you, BUT… I have to say…you’ve read this far, sooooooo maybe there’s hope for you after all? Don’t worry, the “dark side” will be here waiting when you’re ready.

Halt! Your exhausting hunt for stylish comfortable shoes may now end. Our ultimate guide — from statement boots to neutral heels to clog booties — is here.

Shana’s Picks: 1 | 2 | 3 | 4 | 5 | 6 | 7 | 8 | 9 | 10
Linzi’s Picks: 1 | 2 | 3 | 4 | 5 | 6 | 7 | 8 | 9 | 10

The Ultimate Guide To Stylish Comfortable Shoes Right Now

Halt! Your exhausting hunt for stylish comfortable shoes may now end. Our ultimate guide — from statement boots to neutral heels to clog booties — is here.

Comfortable Statement Booties

Comfy Higher Heeled Booties

Comfortable Lower Heeled Booties

Comfy Clog Booties

Halt! Your exhausting hunt for stylish comfortable shoes may now end. Our ultimate guide — from statement boots to neutral heels to clog booties — is here.

Comfy Classic Tall Boots

Slouchy Mid-Calf & Tall Boots

Halt! Your exhausting hunt for stylish comfortable shoes may now end. Our ultimate guide — from statement boots to neutral heels to clog booties — is here.

Comfortable Statement Heels

Comfy Neutral Heels

Halt! Your exhausting hunt for stylish comfortable shoes may now end. Our ultimate guide — from statement boots to neutral heels to clog booties — is here.

Comfortable Statement Flats

Comfy Neutral Flats

If you’re looking for a roundup of comfy fashion sneaks, check out this post or Laura’s chic sneaker post here; for Shana’s look at comfortable sexy heels, go here; and if you’re looking specifically for comfy clogs, there’s one for that too here.

You know I could talk comfort shoes forever and ever and ever….so let’s discuss. What are your all time favorite brands as well as any newer brands you’ve started liking? My all time favs for ultimate comfort are: Danskos, Fly Londons and Fit Flops, but I’ve recently really been enjoying the combined style and comfort of Naturalizer, Gentle Souls and Cole Haan.


*This is not a sponsored post, but a big thanks to Dr. Scholl’s and Everlane for sending over some comfy and stylish shoes for me to try. I am always SO happy to try new styles of comfort shoes, am loving your selections, and SO appreciate your dedication to happy feet.


  1. Love it! I recently got 2 pairs of Naturalizer booties (one western and one combat style) and just went back for a 2nd color in one of them..I teach so I’m on my feet all day and I love how no one can tell they are comfortable (my students have complimented them!)

    • Yay for Naturalizers—when did they get SOOOOO good? I agree…much harder these days to tell which ones are the comfort shoes.

    • I know….so hard to decide! I’m really liking those knit Everlanes as well and I agree….The Bela Vitas are really pretty too.

  2. So many great options here! There’s even flats that I would consider!! ? I really love the Blondo Tallis boots. I definitely want to try them. And I have to agree that Naturalizer is really bringing their A game lately. I really like a lot of their styles, but I’m slightly obsessed with this pair. They made them in green last year and I didn’t get them and have total (non)buyers remorse! Now, I’m in love with the bronze and the blue pairs!
    Thank you, once again, for your super comprehensive post!

  3. This is the round up to end all round ups, awesome! Ok so my challenge is that “comfort brands” are often SO WIDE. Whyyyyyy??? I’m eying those Softt booties but I’m worried they’re not going to work for my banana feet. For some reason I think Shana/Scotti have narrow feet, do you guys mind when you review shoes to indicate your foot shape?

    • I do! Well…not so narrow that I buy ‘narrow’ but narrow enough to totally understand this comment. In general, I’ve had the most luck with Naturalizer, UGGs, Everlane, Cole Haan, Kenneth Cole, and Eileen Fisher.

  4. What a great post! I’m not a “comfort shoe” fan in general (though the older I get, the closer I move to the comfort shoe camp), but SO MANY of the shoes and boots you list here are just beautiful!

  5. Wishlist request: It would be great if you indicated which brands do extended sizing, too. I’ve noticed that some of the go-to comfort brands (e.g. Born, Kork-Ease) don’t go any smaller than size 6/36, whereas I need a size 5.5 even with boot socks on 🙁 (P.S. US/EU size conversion on the small end is different from on the large end, too. 36 is definitely a closer to a size 6 than a 5.)

    I looove Chie Miharas, and FYI they have a lot more sizes/styles available on their website, with free international shipping both ways. They do carry size 35 in all of their styles but I haven’t seen many retailers stock that size.

    • Ugh. I have a friend in your situation and it sounds so frustrating! I’ll definitely keep the extended sizing in mind! Chie Miharas are so incredibly beautiful…so glad they have your sizing on their website. Good to know!

  6. I’ve always given comfort brands the side eye, lol. Recently I’ve had Achilles issues because of the type of sport I do and my feet just can’t take the beating from shoes with little or no support all the time. I’m not getting rid of my shoes but I’m adding in comfort styles as I need to replace or find something new I love. This roundup gives me a great idea of which brands might be good options. Thank you!

  7. I have some major foot issues so I have no choice but to be devoted to comfort brands. Yes, those key words like cushion, arch support, etc get me revved up too! I found the dansko barbara bootie to be more comfortable than the maria: the barbara has really great extra cushion and support! Also the dansko berry clog has the same cushioned footbed as the barbara but in a traditional open back clog with convertible back strap. Naot and Reiker have some very comfortable footwear and I love Ecco and Birkenstock. Check out the Naot Kamsin shoe/bootie: uppers are sooooo soft, footbed is padded nicely and the buckle is actually velcro so quick on/off. Also, the vince Paz loafer (especially in snakeskin!) is so comfortable and stylish with soft upper leather and a padded footbed. Finally, check out the Eileen Fisher Eddy Derby oxford a comfortable and super stylish platform menswear oxford.

    • Yay!!!! Thank you, fellow comfort shoe lover! Good to know about the Danksos–I haven’t tried the Barbara yet. I just got in the Haylene, though, and it’s SOOOOO comfortable. I also love that Eileen Fisher Derby oxford! I haven’t decided if they fit my style, though. Send me a pic, if you can, of how you’re wearing them.

  8. As someone on the opposite end of the feet size spectrum (12/13 depending on the shoe)…I totally agree with this. I regularly click through only to find that most of these don’t come in anything bigger than a 10.

    • I just got mine in and I need to exchange them for a bigger size, but I think I’m going to wear them with mostly black, blue, and gray denim (Skinny, straight leg, and flare) as well as black pants (wide leg and straight). I like Fly Londons with tunics or dresss over jeans…they’re a bit chunkier so I often think a tunic balances out that weight. I haven’t decided yet if they will look good with patterned skirts, but I’m guessing I will also wear them with black tights and a black basic tunic/shorter dress once it gets colder. They’re just so darn comfortable, that when I get a shoe like this I kind of just make them work with a lot of things. So glad you like the blue, too!!

  9. Also, one more note: two brands that are not specifically “comfort shoe brands” but are high priced (and high quality) and thus I think due to superior materials and superior constructions, by default, almost always comfortable in almost all styles are Paul Green and Fiorentini + Baker.

  10. The knit ones and yes, you can walk all day. Super comfortable and I have almost no tolerance for heels with two small kids. I have black and brown.

  11. I am loving Birdies, Vionic, and Chaco right now! Thank you for writing this piece. I am now curious to try some of these other brands! I need happy feet to be happy overall.

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