Most Comfortable Shoes Search: What Are Your Picks?

I have not yet done a whole lot of crowdsourcing here at The Gloss so far, but it seems to have worked out well for all of my colleagues (I was even there when Amanda used your feedback to buy this sweater). Now, I need your help with my feet (and my sanity).

Look, guys, I am in a bit of trouble. Not like “accidentally spilled a slushie on Will Smith” trouble or “can’t stop stripping in public” trouble, but just a bit of annoying, inconvenient trouble. I just moved (again, already) across the country (again, already) from Portland to New York City. While I’m pretty stoked to be in a new place and meet new people, my feet are not impressed. Not one bit.

Having lived in Southern California, a place where driving is ubiquitous and everything’s too spread out to walk to, I don’t own a ton of comfortable shoes. Plus, since I had to donate or throw away the majority of my stuff when I moved last year, I now only own four pairs (yes, that sounds silly to me, too, but most of them are cheap and useless): a pair of bright red ribboned heels, grey pumps, lace-up flat boots, and extremely worn-out heeled boots. None are comfortable, none are practical for constant commuting except the boots, which are currently suffocating my very stressed-out feet, which already have psoriasis and look ridonkulously red and angry all the time, anyway. Now, I’ve acquired these gnar callouses on the top inside portions of my heels. No me gustan.

I’ve gone shopping multiple times this past week, but with no luck. Many of the stores didn’t carry my size, only had high heels or cost well over what I’m cool with spending on shoes (at the most, around $100 for awesome ones).

SO, wonderful readers, I need your help! What are the most comfortable shoes you own and where did you get them? Hopefully, this little post will assist more folks than myself on the subject, since I can’t possibly be the only person tenderly stepping out of her shoes each evening. Thanks in advance, e-buds!

The Most Comfortable Shoes, According to Our Readers

This is pretty much my favorite topic. I’m assuming that you also want cute, since if comfort was all that mattered you could just slap on a pair of Nike running shoes and call it a day. My favorite brands for comfortable but still attractive (sorry, Birkenstocks) shoes that can be acquired for under $100 are Biviel, Miz Mooz, Clarks, Born, and Sofft. You may have to wait for a sale on the Biviel and Miz Mooz, but I’ve never paid over $100 for either brand, so it can happen. I also find Calvin Klein surprisingly comfortable — the regular brand, not the designer one. For more money, try Ecco, Gentle Souls, Stuart Weitzman and Taryn Rose.

I was super excited to share my most comfy shoes, but as I read the post, I realized that my SoCal beach town, staple, comfy shoes, my Reef flip-flops, are not at all practical for what you need at the moment. But if you ever make your way back to California, and are in need of a flip-flop, then I totally recommend Reefs, especially over Rainbows.

I fought it for as long as I could, but they’re so comfortable it’s ridiculous. and you don’t have to buy the ugly clog ones, they actually have some really, really cute ones like this:

Best comfortable Shoes

I own multiple pairs of Crocs ballet flats and sandals. People make fun of me when I say this out loud, but I get tons of compliments when people see my shoes and don’t know what brand they are.

They are a little more expensive, but you can sometimes get them on sale… Cole Haan has a line with Nike Air technology. The Maria Sharapova ballet flats are amazing and last forever. The heels are so comfortable too.

Also…. Born ballet flats, especially if you are walking a lot. But they have this fabric lining and make my feet smell bad.

I don’t care how “creepy” anyone thinks they are, I LOVE my FiveFingers. The fabric between the toes bugs some people, but it doesn’t bother me at all. Once you get used to walking in them, you’ll never go back. It feels crazy naturally. It takes a little while to get used to these since you don’t normally allow your toes to spread when you walk. It’s worth the wait, though, promise! You can throw them in the wash, which is lovely. Also, weirdly, I trip less when I wear them. I’m notably clumsy, so it makes a big difference for me.


Best comfortable heels

  • CMJ:

I know these are probably over your budget but these are THE BEST (for me they paid for themselves within a couple of weeks).

They are comfortable (they take maybe one day to break in) and I have walked all over San Francisco in them (and DC, and Denver, and everywhere really). They have a pretty high heel but the platform really helps, as do the chunky heel. I get SO many compliments on them.

I have a tough time because I own a TON of heels but I very rarely wear them unless I am driving somewhere (which hardly happens as I live in the bay area and I can walk or take public transit) but these have taken me everywhere and look good with EVERY outfit I put together.

Top-Sider Shoes

  • Ashley:

First off, if you’re going to be walking around I don’t believe in open-toe anything (New York is really dirty and if you want black feet, you’re welcome to wear sandals). I also just think feet are kind of gross.

For closed-toe summer shoes, I alternate between sneakers, boat shoes, loafers, and ballet flats. Affordable brands I like: Sperry, Seychelles, Bass, Chelsea Crew…

  • Eileen:

Yup, when I was in college and walked everywhere I wore Top-Siders pretty much all the time (I was wearing topsiders and no socks at Obama’s first inauguration. The no-socks thing was a bad choice.) They run around $60, I think. I wear a lot of flats, too – mainly from Aldo, where the average pair costs about $45 – but they’re less about comfort and more about being reasonably stylish while not wearing high heels (which I don’t wear if I have to walk a lot outside because the heels wear down).

I think one of the main advantages to Top-Siders is, in my experience, they require no breaking in. You can walk out of the store in a new pair and never get a blister.

  • Natalie:

I have a really pretty pair of Sperry topsiders that are a lower cut style, so they actually look super cute for jeans and skits and stuff. They are also neutral beige, so they match everything. Insanely comfy for walking and have a good sole so I don’t fall much. I also put special insoles in them. Usually, I think this style runs around 75-90, but I got them for 25 at Marshall’s! It was a couple of years ago, but they often seem to have great shoes. I’d check there regardless.

I’ve had several pairs of Rockport too. Always a good choice for comfort if the style suits you.

Best comfortable flats

Secret Tip: Check stores aimed at a much older demographic. 99% of the time the aesthetic preferences do not match up, but if you do find a simple pair of ballet flats they’re usually way more comfortable and well built. I learned this by borrowing shoes from a 70yr old. They were pumps that I could walk in for days. Granny, I want your wisdom and your shoes!

  • Maria:

Do they sell Vagabond shoes in the US? It’s a Swedish brand, I have a pair similar to these for fall:

I walked a lot in them in any weather. Not a complaint from me, but lots of compliments from other people. For spring, I have some plain black flats from the same brand. I got them for my mom, too, and she sometimes doesn’t even take them off when she gets home because they’re so comfy. No, I don’t get free shoes for writing this (or do I? Contact me, Swedish shoemakers!). They’re the best!!

I read somewhere that flight attendants love to wear this brand of flats during in-flight service:

So I’ve bought and worn a few pairs now. I’ve never found a pair that was truly chic, but they’re really comfortable, especially if you buy heel liners (which cost a few dollars per pair, and they keep flats from shredding your heels). They’re also cheap enough to not feel guilty when you eventually run them into the ground, as always happens sooner or later with flat shoes.

  • Tania:

Ballet flats. I get blisters ridiculously easily, so I gravitate towards shoes with soft cloth/stretchy heels otherwise I have bloodstained shoes which are not very nice.

I shop around until I find shoes that fit that criteria and then I buy the hell out of them.

  • Daniela:

I’ve found some pretty comfortable flats at Payless, but it’s kind of hit-and-miss. (And by comfortable, I mean they had pretty good arch support and whatnot.)

If you have to, I guess you could buy slightly less-than-comfortable shoes and get those insole thingies (yes, that’s the technical term). I’ve never used them, but they seem to work. (And as a plus, you could be gellin’ like a felon.)

  • Alle:

I pretty much just buy $30 ballet flats from DSW every year, wear them into the ground and then throw them out. I wouldn’t say they are “comfortable” exactly–I have a high arch and sometimes it gets sore, plus a narrow heel prone to blisters–but they get me from point A to B and look pretty decent. If you find a pair you like and it comes in two colors, buy both. I’m always glad when I do this. Also, check Zappos.

  • Meghan:

I second the Cole Haan recommendation and have had good luck at the outlet as well–I know I’ve purchased flats for around 75 that way for sure– but I actually got two GREAT pairs of comfy flats from the Dr. Scholl line–I think I got them at DSW. They were 30 bucks a pop, and have held up surprisingly well since I walk hard.

But I feel you can improve the cheapest of flats with good insoles, too.

Best comfortable boots

My MOST COMFORTABLE shoes are boots, which I wear year-round and don’t even care if it’s gross. Frye boots are the best, and I know they’re expensive, but man does they hold up. You gotta anticipate some break-in time, though it’s usually only a couple of days.

Ok, so I live in Texas & as much as I hate Texan stereotypes (no, I don’t ride a horse to work because we have NASA… we can fathom modern transportation) (that is really something my boyfriend’s friends from England think) I love, love, love, love my cowboy boots. They are Madden Girl (so, they are vegan cowboy boots. only in Austin will you find Vegan cowboy boots in Texas), they cost like $50 & I wear them with everything. I wear them with cute sundresses, shorts & boho tops, leggings. Hell, when I go to walk my dog first thing in the morning I wear them with my PJ’s. They are so comfy to slip on & I can walk in them for miles without hurting my feet. I don’t know if this will fly on the reg anywhere else in the world, but I love them. So hard.

Best Comfortable Ankle Boots

Best Casual Ankle Boots

Get yourself around in a pair of these. I have a pair that has a thin ankle strap (for decorative purposes) and they are the best. Give them a Scotchguard the first time you wear them, and then polish them (properly, like with a brush, tin of polish, and cloth) every 10 days or so. Well-made, comfy, and sleek enough not to look too daggy. I have worn mine to a classical guitar recital with an evening dress, wear them all the time with jeans, am wearing them with a sundress right now. All. The. Time.

I walk around all year round in my Adidas stan smith II black. I alternate with simple black converses (when it’s not raining). Other shoes such as high heels hurt my sole very fast and after a while my back. One exception is shoes made by the Spanish brand campers, I’ve got this model in dark blue suede: they’re very comfortable and quite stylish but expensive…

Spanish Brand Campers

Most Comfortable Wedges

The most comfortable pair that I own are my TOM’s Wedges. Seriously, I pick them over flats all the time.

I got a pair of flats that kind of look like Tom’s at Target, they are sparkly black and $20 (though they had a bunch of different colors.) They are comfortable enough to bartend/waitress in all night. Usually, shoes with no socks tear up my feet but these actually didn’t. Go fig.

I was in the same situation when I moved here last year. You’ll notice that your shoes are going to wear out much more quickly – also, heels are bad and flexible soles are good. This spring/summer I’m ready with flat sandals with an ankle strap from Target, Minnetonka moccasin flats, and a pair of knock-off TOMs. Do you need to wear nice shoes for work?

Birkenstocks!! For work, my born heels and boots are the BEST. I also have a pair of Mia sandals that are revolutionary for summer workdays.

What Is The Most Comfortable Pair Of Shoes You Own?

What Is The Most Comfortable Pair Of Shoes You Own?

When I say my shoes are literally falling apart, I mean it. As you can see in the above photo, there is a big ol’ hole going clear through the sole. These are a pair of Marc Jacobs flats I bought at a Crossroads in Los Angeles a couple of years ago for $50, which means somebody else wore ’em first, and it was only a matter of time before I wore a hole through them. I’ve been on a fairly limited budget since college ended in 2012 and have therefore practiced that ill-advised (but often necessary) habit of purchasing cheap items regardless of quality, but now I’m ready to invest in a good pair.

When I moved to New York two years ago, I just assumed I would be able to keep wearing my kitten heels and high-heeled boots, but my choices resulted in more blisters and callouses than I can count. So, now I’m searching for shoes I can actually head to work in — ones that are comfy enough to walk for a couple of miles without aching and high-quality enough to wear all summer without getting holes in their soles.

I truly hate flip-flops and most sandals, but I understand why people wear them: they can be super comfy. I’m searching for the best pair of everyday shoes, preferably flats, but I am open to just about everything else. This past fall, our lovely writer Kelsey found the perfect pair of boots that went with everything she owns, and now I want to do the same. My budget is $300, so anything under that, and I’m ultra open to it. If it’s more than that, feel free to mention it because, hey, there’s always The Outnet!

What’s the most comfortable pair of shoes you own? Tell me in the comments and help me rescue my feet!

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