This post started out as the two types of comfort shoes I’m actually wearing….and those two shoes of course were #1 “House Shoes” and #2 “Sneakers with SuperFeet”…the end. With the crisper weather, though, this post quickly and excitingly evolved to include seven categories of shoes I’m actually wearing…your usual Linzi Monster Shoe Post. I forgot how much I LOVE fall boots and clogs…and providing ALL the comfy options.
*To Shop A Specific Category, Click On The Comfort Shoe Table Of Contents Below Or Go To Shana and My Top Picks Here.*
Comfort Shoes For Fall & Winter (By Category)
Table Of Contents
1. Casual Booties (Low Heel)
Incorporating my new comfy Fly Londons while doing the afternoon kid-activity schlep.
2. A Bit Dressier Booties (Higher Heel)
Wearing walkable higher-heeled boots when I’m allowed to leave the house SANS children…total mood boost!
3. Clogs
These clog boots for outdoor hang-outs, but THESE lined Dansko clog boots when it gets super-cold.
4. Fashion Sneaks
Getting SO much use out of these cute Madewell sneakers (with SuperFeet if I’m walking ALL day).
5. House Shoes
Ummmm….maybe the most important category this year? I decided my toes needed more freedom, so these in black are arriving soon.
6. Cozy Snow Boots
My older version walkable snow boots from the same brand are lined up and ready for physically distanced snow hangouts.
7. Date Night (Or Work) Shoes
I wore these heels last week. Yes…Heels! Real Heels! Much needed date night, and I felt fabulous in them.
**I always give a disclaimer that comfort shoes (especially boots) are expensive. Really expensive. In general, though, I have found that I get a ton of use out of my high-quality comfort shoes from well-respected brands. If there’s a style I truly love that makes my feet happy, it has been worth the money for me. I wear them for years and years. For budget-friendlier comfort, my suggestion is to take advantage of when these brands go on sale! We’ll share on IG when our favs are discounted, or click on the heart below your favorites below and you’ll automatically get a notification when they go on sale!
Fall & Winter Comfort Shoes: Our Top Picks
Lots of options, lots of brands, lots of styles, but with the glorious common thread, of course, of lots of comfort. Let’s get started…
Linzi’s Picks: 1 | 2 | 3 | 4 | 5 | 6 | 7
Shana’s Picks: 1 | 2 | 3 | 4 | 5 | 6 | 7
The 7 Styles Of Comfort Shoes I’m Actually Wearing
1. Casual Low-Heeled Boots
At Nordstrom | At Zappos | Higher Shaft Version (that I LOVE)
In Browns, Tans & White …
…Or Easy Black.
SUPER-Cozy Options Too.
2. Just-A-Bit Dressier Higher-Heeled Boots
In Earthy Tones…
…Or Chic Black
Playful Options Too
3. Clogs, Clogs, Clogs
At Amazon | At Etsy | At Lotta
In Clog Shoe Styles…
…Or Clog Boots
**Check Out Laura’s Comparison Of No. 6 Vs. Swedish Hasbeens Here. **
4. Fashion Sneaks
Lighter Shades
Darker Shades
Truly Bold
5. Comfy House Shoes
At Nordstrom | At Zappos | At Backcountry
Comfy House Shoes
6. Cozy Waterproof Snow Boots
At Nordstrom | At Zappos | At Backcountry | At Sorel
Cozy Waterproof Snow Boots
7. Date Night (Or Work) Shoes
Flats & Heels
Shout out what comfort shoes you guys are loving…you know I’m always happy to hear about other people’s happy feet as well!
For you wide and narrow ladies, I’m once again disappointed in the selection for you guys. Was excited to see some cute options from Walking Cradle, Vaneli and of course Naturalizer, but feel free to shout out any brands you’re loving in the comments for other narrow and wide folks.
Look for my pros/cons of the shoes I tried soon-ish! There are A LOT this year!
-Linzi
ps. this one’s for the pinners…
Have you tried Allbirds? I haven’t, but love the idea of cozy wool sneakers! (Glerups are the best ever slippers, so . . .)
I have! I have a pair of Allbird slip-ons, and they are fabulously cozy. I actually wear them a lot as a house shoe because they feel JUST like a slipper. I’ve also brought them along on travel as they are pretty much ideal for slipping on and off during long flights. The slip-ons I have don’t provide as much arch support as my feet would like in terms of all day walking on pavement, but they are definitely super cozy. I love the look of the new wool pipers (https://shopstyle.it/l/bnSjG), and I’m also SUPER interested in trying their weather-repellant winter sneakers (https://shopstyle.it/l/bnShq). Love the idea of a soft cozy (not too heavy or clunky) winter sneaker that keeps your feet warm and dry. I’ve never actually tried Glerups, but now they’re on my list too. Thanks, Sara!
Linzi, as usual, you ROCK! How is the width on those Fly Londons? Any chance you could measure across the toe box for me? I’d buy them in a heartbeat if they might fit!
Thanks, Jen! Always good to hear from you. 🙂 And of course I’d be happy to measure across the toe box for you. You have to give me specific instructions, though…Where exactly do you want me to measure? The widest part of the toe box before it starts to narrow at the actual toes? Across the top of the shoe? They’re not super wide, but they have some give, so they may mold to your foot. I LOVE them. As of now, they’re my favorites of the new shoes I’ve tried this year. So comfortable!
Has Linzi/can Linzi do a post on jeans that aren’t skinnies and look great with some of these chunkier comfort boots? I love all the jeans in this post!
Haha…I am definitely not a skinny jean gal…I wear them because they tuck so nicely in to my winter snow boots, but I’m definitely a fan of straight, flare, and wide-leg jeans. I’ve been meaning to do a jean post, so I’ll hopefully get to it sometime in November. In general, my favorite brands are Madewell, Mother, Everlane, and Good American. In the post, I’m wearing Madewell Cali Demi’s (https://shopstyle.it/l/bnST6), Mother Tomcats (https://shopstyle.it/l/bnST8), old jeans VERY similar to these (https://shopstyle.it/l/bnSUg), Mother The Weekenders (https://shopstyle.it/l/bnSUk), and my favorite stretchy skinnies from Good American (https://shopstyle.it/l/bnSV6).
Yep, the widest part of the toe box, across the top of the shoe (or bottom), is what to measure. You are a queen!
Okay…I tried them on again and measured them, and I don’t know if they’re going to work for you, Jen. Across the bottom they’re only about 3.75 inches wide at the widest part on a size 7.5. The suede ones feel like they have more give than the leather in terms of stretch, but they’re definitely not wide. 🙁 I’ve been looking for something sort of similar for you…the Yami from Fly London comes in wide sizing in black leather as well as forest and wine suede (https://shopstyle.it/l/bnUli), but the wedge is the more traditional Fly London wedge, not the one on my boot. 🙁 If you end up trying the Fly Londons I have let me know what you think and if they will stretch enough for you. Good for me to know. 🙂
Great picks! I have the same fuzzy Birkenstocks in black as my slippers! … for downstairs, because at my house, it’s cold downstairs on the slab, and hot upstairs by the attic furnace. My favorite boots/booties in your Higher Heel category are the Teva Foxy style (yes, Teva!). I have them in black and beige and they are comfy AND water resistant.
The fuzzy Birks are definitely dreamy. And so glad to hear you’re loving the Tevas. I’m always so happy when trusted comfort shoe brands branch out a bit with their styles.
I always look forward to your shoe round-ups, Linzi! Do you find the Fly Londons to run true to size, allowing for socks? I have been coveting the Fly London Lita, but wasn’t sure about sizing. Thanks!
Awww….thanks, Angela. I usually a wear a 7 in sandals and a 7.5 in boots. The Fly Londons I got this year are my usual 7.5, and they are super comfortable for my feet, but not especially roomy. They fit me with just the right amount of snugness…I imagine they will stretch out a bit, but if you wear REALLY thick socks I would consider sizing up. Also, the suede ones feel like there’s more “give” in them than the black leather. Hope they work out for you!
Ok, super weird request. I want to wear all the cozy, ankle covering shoes possible, but I live in So Cal. Do I wear a lined high top, stick to my usual casual uggs? Love all the options you posted! But would I look ridiculous in San Diego? 🙂
Oh man, Christa. I was hoping some readers from warmer climates would maybe chime in here. I have no idea! My first reaction is if you love cozy ankle covering shoes then GO FOR IT! Who cares if someone thinks you look ridiculous if you love your boots and feel good in them. If you want to blend in a bit more with warmer climate looks…maybe go with lighter toned boots…they feel fresh and sunny to me and overall have a lighter look that may work better for you?? I wear my off-white boots in warmer weather for sure. Hopefully someone else with more experience in this area will chime in!