Yep…20 pairs of comfort shoes, guys (actually 21 because I just threw in a bonus pair!) No one can say I’m not committed to this “endeavor”. Each season I research, try, and test out lots of shoes and then share with you guys my pros and cons for each pair. If you’re looking for the quick answer: My most-worn boots are these Fly Londons, Danskos, Vince & Glove Boots. My most-worn sneaks are these Court Sneakers & these Trainers, and my most-worn house shoes are these dreamy guys.
Shearling Sandals To Waterproof Booties: 20 Stylish, Comfortable Pairs Of Shoes & Boots Reviewed
If you’re looking for the longer answer…I obviously have you covered. My mission is finding the most stylish options BUT keeping in mind practicality, versatility and of course comfort. Of the shoes and boots I tried this season, 10 of them I loved, and 10 of them weren’t quite right for me (but they’re great shoes from great brands, so they might be right for you). ALSO — I have a not-to-miss bonus pair of waterproof boots that JUST. CAME. IN. Click here to see them first (but only if you promise to come back and check out the rest of my research :-).
Let’s get to it! I mean, we have a lot of shoes to talk about…no more wasting time!
10 Most Worn & Loved Comfort Shoes
1. Vince Henderson Chelsea Boots
PROS: I’ve been raving about these since this summer. They magically look good with every style of denim I own. Comfortable. Luxe looking. 5 colors (but sizing is VERY limited now). Waterproof. Nine ways to wear these booties here.
CONS: Pricey (but currently on super sale!). Because of the crazy good sale, sizing is limited in certain colors. I can walk in them one to two miles no problem, but I would choose my Fly Londons or Danskos if I was going to be standing all day long.
Boots At Nordstrom
Sweater | Denim | Bag (Similar)
2. Fly London Lede Booties
PROS: SUPER-comfortable. Can walk in them all day. Feel similar (or even better ) than some of my sneakers. Nice high shaft that’s perfect for cropped denim. Work with skinny denim as well. Three practical colors available. Why Fly Londons are my favs, here.
CONS: Pricey. Shiny leather sold out in most sizes, but suede (on right) still available.
At Nordstrom | At Zappos | At QVC
Sweater | Denim | Puffer | Hat
3. Everlane Glove Boots
PROS: Sustainable pick made using recycled materials. SUCH good color and fabric options. Nice high shaft for cropped denim. Surprisingly comfortable. Neutral colors are lovely, but the pops of fun color or fresh white/ivory are my favorites. No other boot brand I like has as wide range of color options. Easy way to elevate a simple look.
CONS: Lighter colors get dirty easily, but spot cleaning has worked for me. No tread on sole. Not good in bad weather. Can walk in them a mile or two easily, but wouldn’t select these for standing/walking all day.
4. Birkenstock Arizona Shearlings
PROS: SO super cozy. Supportive. Good for toes that like to wiggle. Great for those of us who get overheated easily, but still want some warmth and support for their feet around the house (have also been wearing them with my Smartwool socks on extra cold days). Tons of cute colors available. Can wear them outside as well.
CONS: This is my first time owning shearling lined slippers–can’t decide if the shearling will be gross after a full winter of bare feet in them. Have been VERY popular, so you may have to check multiple retailers listed below for sizing/color preferences.
At Nordstrom | At Zappos | At Free People | At Birkenstock
Sweater Hoodie | Sweater Joggers
5. Dansko Shearling-Lined Clog Boots
PROS: Standard Dansko comfort and support (my feet LOVE Danskos!). Three great colors. Can be folded over for a shorter bootie look. Lined only on boot shaft (good if you get overheated easily or like more toe wiggle room). Perfect warmth for me with cozy socks. Super-easy to slip off and on.
CONS: Run big. They aren’t fully lined (for those of you who like shearling in the footbed too).
At Nordstrom | At Amazon | At Dansko | At Zappos
Puffer | Denim (Similar) | Hat
6. Everlane Court Sneakers
PROS: Super-comfortable. Simple but cute styling. Sustainable features (natural and recycled rubber sole, 100% recycled lining). Leather is easy to spot clean. Some colors on SUPER sale. I don’t put my SuperFeet in these, and I can still walk long distances.
CONS: Style not for everyone–very simple.
White | Black, Gray, & Rose
Denim | Sweater Hoodie
7. Madewell Kickoff Trainers
PROS: SUPER-cute pattern and color options. Athletic sneaker look, but with fun designs. Walked many miles comfortably (but did put in my beloved SuperFeet for extra support).
CONS: Much heavier than I expected. A little stiff (was expecting more of an athletic sneaker feel).
8. New Balance 574s
PROS: New Balance 574s have been my go-to sneaker for a long time. Comfortable enough for me to workout in/take dance classes in and cute enough to wear as a fashion sneak. I do put in my beloved SuperFeet for extra support when walking long distances.
CONS: I need SuperFeet in them if I’m going to be on my feet all day long.
At New Balance | At Bloomies | At Zappos
9. Cole Haan Vania Half D’Orsay
PROS: MUCH more comfortable than they look. Cool design. Sexy look.
CONS: They’re still heels…I personally would NEVER wear them all day long. They keep selling out!
10. Lotta Clog Boots
PROS: Nice high boot shaft that’s perfect for cropped denim. Gorgeous tan color. Beautiful wooden heel; Super comfortable (if you like the feel of wooden clogs). I personally LOVE the styling of these.
CONS: Lotta Emma boots sell out SO fast every year. Only a few sizes left, so next fall when I tell you guys they’re back in stock JUMP on them!
At Amazon | At Lotta | At Etsy
Cashmere Hoodie | Denim (Similar)
10 Great Comfort Shoes: But Not My Favorites
11. Fly London Chelsea Boots
PROS: Everything is wonderful about these—comfortable, modern and supportive, but I just LOVE the higher shaft of the Ledes better. If you like a lower-shaft chelsea style, though, these are fantastic! Why Fly Londons are my favs, here.
CONS: For me personally, I wanted a higher boot shaft so I prefer the Ledes.
At Nordstrom | At Zappos
12. UGG Hazel Waterpoof Block Heel Booties
PROS: VERY similar style to the Vince Hendersons, but at a much lower price. Nice chunky tall heel, but still walkable.
CONS: Wider at the ankle than the Vince booties, so not quite as sleek. Not as luxe-looking as the Vince’s, and not as smooth when walking.
At Nordstrom | At Zappos | At Ugg
Blue Denim | Black Denim (Similar) | Sweater | Bag
13. Sorel Joan of Arctic Next
PROS: Super-cute styling. Several great colors available. Lightweight. Comfortable.
CONS: The only reason I didn’t keep these is I already have two pairs of winter boots that I love.
At Nordstrom | At Zappos | At Sorel
14. Sorel Harlow Waterproof Chelseas
PROS: Lightweight. Feel like a sneaker on. Have a nice “boing” when walking. Several good color options. Love the contrasting tread.
CONS: A little snug pulling on (thinking the zip version might be better for me). Wish shaft was higher for cropped denim.
At Nordstrom | At Backcountry | At Zappos | At Sorel
Denim (Similar) | Sweater
15. UGG Markstrum Waterproof Chelseas
PROS: Cool modern styling. Love the heavy lugged sole look. Waterproof. Three colors.
CONS: A bit clunkier to walk in than I wanted them to be. A bit stiff for me. More comfortable once I put on thick cushy socks.
At Nordstrom | At Zappos | At Ugg
Denim (Similar) | Sweater
16. Birkenstock Shearling Lined Clogs
PROS: Super-cozy. Super-warm. Supportive
CONS: My toes wanted more freedom. I ended up buying these instead.
At Nordstrom | At Zappos | At Amazon
17. Aquatalia Block Heel Booties
PROS: On super sale. Aquatalias are loved for their high-quality and classic styling. They’re comfortable, super-soft suede. Weatherproof. Beautiful wooden heel.
CONS: Limited colors/sizing left. Wish they had a slightly higher shaft.
At Nordstrom | At Nordstrom Rack
Denim | Black Sweater | Mushroom Sweater | Bag
18. Madewell Clog Boots
PROS: A nice looking clog boot. Good pricing for clogs (especially on sale). Pretty leather. Three color options (including a fun animal print). Soft cushy footbed.
CONS: Too narrow and stiff for me. I didn’t even take a photo because my feet were NOT happy in them.
19. Madewell Sidewalk Low-Top Sneakers
PROS: Cushy footbed. Comfortable overall feel. Great brown and navy detailed colorway. Good price (especially on sale).
CONS: No cons…other than I personally just gravitate to the similarly styled Everlane court sneakers more.
20. Madewell Slip-On Clogs
PROS: Supportive. Comfortable footbed. Easier to walk in than I thought they would be. Nice option for a fall or spring slip-on.
CONS: A little narrow. I prefer this style of clog slip-on from Madewell, so hoping they may bring it back.
**Bonus (Just IN!)
UGG Waterproof Boots**
PROS: SUPER-warm, SUPER-comfy, SUPER-cute! UGG plush coziness. Adjustable strap and ties for perfect fit. Available in a great brown colorway as well. Winter UGGs without TOTALLY looking like your typical winter UGGs! Such a fan!
CONS: They look a little bulky if you have very skinny legs and are a skinny-jean-wearer. Shana tried the brown, and she was a little disappointed with the proportions on her.
At Nordstrom | At Zappos | At Ugg
Denim | Sweater | Socks
Phew!!! If you made it this far, I applaud your commitment to comfort shoes. I’m there with you, obviously. As always, feel free to shout out any favorites you want to share with our readers and thank you so much for reading.
I really love how those leather Fly Londons look. I may be making my first foray into the world of true comfort shoes soon! Do you think Santa knows about them? 😂
YES! Finally, Elizabeth! Don’t worry. You can always alternate…one day your crazy high pointy stylish heels, then the next day cushiony heavenly oh-so-practical comfort shoes. As always, thanks for commenting, and Santa should obviously be reading the blog if he isn’t already. 🙂
I love your comfort shoe reviews! Keep em coming!
Thank you, Chris. Appreciate it.
O comfort shoe queen, please tell me… how do you wear sneakers barefoot?! Or find socks that don’t show at all but also don’t slip down off the heel?
With the exception of knit-upper (and non-waterproof) sneakers like the Nike Flyknit, I find sneakers LESS comfortable than many other shoes in my closet. Unless I wear a sock that completely covers the achilles tendon — which is not a fashionable look these days, alas — they tend to rub there, no matter the price point of the sneaker. And when going barefoot my toes get rubbed too, even though I have narrow feet. Maybe *because* I have narrow feet, I’m getting more movement/friction? Help! I would love to wear cute sneaks without socks, but they’re so uncomfortable…
Well first, off…you should probably get some sort of prize for addressing me by my proper shoe royalty name, Keilexandra. You totally made me laugh out loud when I opened up the comments on this post. I don’t wear sneakers barefoot…this may be TMI, but my feet are WAY too sweaty to not wear socks…my shoes and feet would be disgusting, and I also personally don’t find it comfortable to wear sneakers without socks. I have found a few no-show socks that don’t slip down off my feet and actually don’t show. These Zella socks (https://shopstyle.it/l/bpFXu) and these Stance socks (https://shopstyle.it/l/bpFY3) fit my feet well. I realized that I can only wear no-show socks that come in multiple sizing…otherwise they’re too big and slip down. The silicone heel grips help on these two pairs as well. I don’t think those are going to come up high enough, though, to solve your “rubbing against the achilles tendon” issue. 🙁 Maybe just match your higher sock with your shoe color or pant color?… or go bold and wear a fun design or pattern? I’ll let you know if I come across any no-show socks that come up high in the back, but lower on the sides…that’s probably what you need, right?