The 6 Comfortable Shoes (Many On Sale!) I’m ACTUALLY Wearing This Winter


Yet again, this winter I’m finding myself scouring websites for brand-new, on-trend, comfortable shoes.

Ordering and returning; more ordering and returning; a few in-person retailer visits; some ordering, wearing and then donating; and then, yes…more ordering and returning. Searching for something REALLY exciting in the world of comfort shoes.

But after trying out quite a few of these new and exciting shoes this year…you know what I keep coming back to? 

The oldies — but goodies — in my closet.

6 Tried-&-True Comfort Shoes I’m Wearing This Winter, Ft. UGGs, Birks & More

Comfort shoes. I try to find new, on-trend footwear, but I always go back to my 6 tried-&-true pairs. Think: cozy UGG boots, walkable Naturalizer heels & more.

Vagabonds | lined Danskos | similar Danskos | jeans (left) | jeans (right)

You’ve seen a lot of the shoes I’m talking about in my “most-worn” posts of previous years, you’ve seen them in my selfies, and if you’ve ever crossed paths with me in Philly, you’ve ABSOLUTELY seen these comfortable shoes on my feet.

These are the shoes I ACTUALLY wear, and good news for ALL…several are on sale because…FEBRUARY!

Quick cheat sheet below of my most-worn comfortable shoes I’m wearing this winter, BUT if you have a few minutes, keep scrolling for all the good stuff. You’ll find similar alternatives to my fave shoes (since a few of my older pairs are low in stock), close-up selfies, links to several retailer options so you can find your size (many on sale!), and a video review of me chattin’ it up about these oldies-but-goodies top picks.

*If you’re shopping the cheat sheet and your size is sold out, keep scrolling for other retailers and similar options.

My 6 Most-Worn Shoes Of Winter

I’m actually OK with the fact that I didn’t fall in love with any of the new and exciting on-trend shoes out there this year. There’s something super-satisfying about realizing that what’s already in my closet is better than anything new I’ve tried. No need to buy something new…or for the pairs that do need a refresh, I can just order a new color or a slight variation of what I already have and know I’ll be happy! 

You likely won’t be shocked by the appearance of my beloved comfort-shoe brands Birkenstock, Dansko and UGG…but there are a few other brands in there too that have been sitting in my closet for a bit and have been recently rediscovered. And then, there’s one new and shiny pair of shoes from a brand I’ve loved FOREVER to add to the mix for fun. 

If you have a chance, put in the comments your own most-worn comfort shoes of winter (anyone else shopping their closet?). I always love hearing from you and could talk comfort shoes!

1. Vagabond Cosmo 2.0 Lug-Sole Chelsea Boots

I'm usually a 7.5 in boots, but I wear a 37 in Vagabond's Cosmo 2.0 Chelsea boots, & they fit fine.

At Nordstrom | At Zappos | At Urban Outfitters
jeans | sweater

My go-to outfit-making boots. They just make EVERYTHING look better. I didn’t wear these Vagabond Chelsea boots very much when I first got them (last year…maybe the year before?) because they aren’t from one of my typical comfort-shoe brands, and I just assumed they wouldn’t be comfortable enough for my daily urban walking routine.

BUT I was WRONG! So glad I decided to give them a try (from the back of my closet) this winter as a pair of everyday city boots — I couldn’t be happier. More details in the video, but these guys are GOOD! I’m usually a 7.5 in boots, but I wear a 37 in these, and they fit fine.

More Modern, City-Walkable Chelsea Boots

2. Naturalizer Mallory Platform Sandals

I've walked HAPPILY on city sidewalks to events in these Naturalizer heels & danced all night on several dance floors. They're also perfect event & wedding shoes...

At Nordstrom | At Zappos | At Naturalizer
jeans | top | earrings

OK….so these strappy sandals are new this year, BUT they’re from my fave comfort brand, Naturalizer, which is a brand of heels I’ve worn and loved for years and years and YEARS! I attempted to branch out with heel brands this fall (feel free to check out my review on Sarah Flints), but I ended up wearing on repeat my tried-and-true Naturalizer heels.

And these new Mallory heels are AH-MAZING! I’ve walked HAPPILY on city sidewalks to events in these, danced all night on several dance floors, and have also done just fine all dressed up, standing for hours, and making small talk while wearing them (well, physically fine…mentally, I was exhausted — true introvert).

Wearing a 7.5, my usual Naturalizer heel size. And if you’re going to any weddings or special events this spring/summer, keep an eye on these heels here…Naturalizer will come out with spring materials and colors soon, and last year’s were adorable!

More Comfortable Heels From Naturalizer

3. On Cloudswift Running Shoes

I'm happy with my usual 7.5 shoe size in all the On Cloud sneakers I've tried, even the Hikers, which reviewers have said to size up in.

At Nordstrom | At Zappos | At Free People
joggers | tank

This winter I decided I REALLY wanted to love HOKA shoes. Everyone is wearing them, and they ARE ridiculously comfortable, but the style just wasn’t right for me (full post here). What I’ve been wearing instead? My old On Cloudswift sneakers.

So…for a refresh, I ordered three brand-new, all-white pairs of On Clouds and am now having an extremely hard time deciding which ones to keep. I truly love them all! Post coming…but I tried the On Cloudaway Hikers, the all-white On Cloudswifts and the On Cloud X3s. All fantastic sneakers that look cute enough to wear with jeans but are also great for exercise.

I’m happy with my usual 7.5 sneaker size in all the On Clouds I’ve tried, even the Hikers, which reviewers have said to size up in.

More Cute & Practical On Cloud Sneakers

4. Shearing-Lined Birkenstock Slip-Ons

L: At Anthro | At Zappos | At Backcountry
R: At Anthro | At Zappos | At Saks | At Nordstrom

Oh, shearling-lined Birkenstocks. I can’t stop talking about you. You are just too TOO wonderful on my feet, and I predict I will continue raving about you for years to come.

Specifically, I love the lined Buckley slip-ons (for fall out-and-about and winter road trips) and the lined Arizona slide sandals for my go-to house shoes. They’re just…lovely. Cozy and supportive and soft and comfy — and now on sale at several retailers. Woo-hoo!

Note: The lined Boston clogs (that tons of other folks love) are too stiff for my toes, which like to wiggle. In the Buckleys, I wear a 38, and in the Arizonas I wear a 37. Typically, I’m a 7 in sandals and a 7.5 in boots for reference.

More Lined Birkenstock Slip-Ons & Slides

5. Dansko Lined Clog Boots

The newer version of Dansko's clog boots is just as comfy, but they do have a different vibe in design.

newest version at Zappos | newest version at Amazon

The boots that should likely be retired. I mean, I do have newer more fashionable clog boots in my closet…but nope. I can’t do it.

Yes…my specific Danskos could definitely use some love from the shoe-repair place or the dry cleaners — or at least a shoe-shining place (do we still do that?). Instead, these clog boots have a nice little spot reserved (as is) next to the front door, and they’re the boots I gravitate to MOST on early morning drop-offs for 6 a.m. sports practices. And quite often, they’re the boots I gravitate to any time I’m walking out the door and just want something comfy and easy.

Dansko no longer makes my specific boots. There are a few pre-worn pairs on eBay or you can check Poshmark. The newer version of these boots is JUST as comfortable (and on MAJOR sale), but they do have a different vibe in design. Hoping Dankso will bring these back in more colors next year!

More Updated Clog Boots

6. UGG Classic Weather Hiker Snow Boots

These UGG Hiker boots are cushiony, soft, supportive, & have been nothing but pleasurable to wear on icy, snowy surfaces.

At UGG | At Zappos | At Amazon

Well…I tried. I was hoping to find new brown — or beige or tan — comfortable, warm, cute snow boots for my ski mornings and snowy cold walks in Philly. But nope… In the end, I just ordered the brown version of my tried-and-true black UGG Classic Weather Hiker boots for a snow-boot refresh.

I’m going to switch out the red laces with black for a different feel (and so I can wear them with my green ski stuff without looking like a Christmas tree).

These UGG Hikers are cushiony, soft, supportive, and have been nothing but pleasurable to wear on icy, snowy surfaces. If it’s not broken…

Sizing is limited, but there are a lot on sale, so like the Danskos, I’ll keep an eye on if UGG brings these back (or a similar version) next winter. I wear my typical size 7.5 for boots.

More Cozy-Cushy UGG Boots

And for even MORE chatting-it-up about the comfortable shoes I’m actually wearing this winter, check out this video on our TME YouTube channel.

Let me know in the comments your own most-worn comfort shoes this winter. I adore comparing notes with you fellow comfort-shoe lovers. Anyone else fall flat in finding something new and exciting this year in the world of winter comfort shoes?


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Pinners, don’t pass these up! We made them just for you…

Comfort shoes. I try to find new, on-trend footwear, but I always go back to my 6 tried-&-true pairs. Think: cozy UGG boots, walkable Naturalizer heels & more.
Comfort shoes. I try to find new, on-trend footwear, but I always go back to my 6 tried-&-true pairs. Think: cozy UGG boots, walkable Naturalizer heels & more.


  1. Still obsessed with my mid heel shearling clogs from No. 6. I find them so comfortable and they give me a little height. They don’t work for super cold temps, but I wear them out and about with socks when it’s in the upper 30s.

  2. Hi! There must be a better place to ask this question…but what shoes is Shana wearing on the “35 ways to wear a white tshirt” guide cover? I already subscribe so can’t figure out how to get the guide. But those look so much like a pair I saw on the London subway last week (that I’m trying to match). Any help is appreciated… Thank you!!!

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