My 5 Most-Worn Comfort Shoes This Winter (Many on Sale!)

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The majority of my most-worn shoes this winter are the ones I’ve been wearing and talking about for years. I wore many of them last winter, some the winter before, and I am anticipating wearing these workhorses for years to come. Cute, comfortable and timeless shoes are difficult to push aside…even as fresh new shoes enter the mix (and there are some of those, too).

My tried-and-true shoes are a simple, easy to slip oon & off, very casual + ULTRA-comfortable for walking the city pavement (or hard kitchen floor) all day long.

At Zappos | At Nordstrom | Non-Buckle Version
Denim | Coat | Hat

I assure you I’ve been TRYING to find new, exciting boots and shoes that meet my VERY high comfort standards. I shopped all winter in search of boots that were different and on-trend, but would still deliver on my walkability requirements.

The 5 Boots & Shoes I’m Wearing On Repeat All Winter

Before we get into my go-to shoes and boots this winter, a quick shout-out to these Vagabonds that are totally “comfortable enough”. I wear them quite often when I instantly want my outfit to feel more current. Another shout-out to my brand new comfy winter sneaker-boots (super-cushiony and cute) and these fancy gorgeous new clog boots (that make every outfit look better). But…none of these are my actual most reliable shoes for the day-to-day. My tried-and-true shoes are a bit simpler, easy to slip off and on, very casual, and ULTRA comfortable for walking the city pavement (or hard kitchen floor) all day long.

**WARNING: It’s the end of the season and there’s limited sizing in some of my favs.
I included multiple retailers when available if you keep scrolling, as well as similar options.**

Most-Worn Boots for Everyday: Olive Chelsea Boots | Similar

Most-Worn Winter Boots on Super Cold Days: Stylish Uggs | More Sizing

Most-Worn Boots for All Day Walking: Clog Boots

Most-Worn Work Out Sneakers: On Cloudswift

Most-Worn House Shoes: Cozy Birkenstocks


1. My Favorite Booties For Everyday: Olive Chelsea Boots

 I ordered these Chelsea boots because of the color (and the price). They're one of the MOST comfortable boots I own, I love the simple style, they're easy to take off and on & the green works with almost everything.

At Nordstrom | SUPER similar more sizing

Surprise hit of the winter. I ordered these Chelsea boots because of the color (and the price) but thought seriously about returning them (I have other green Chelsea boots in my closet). I’m so glad I didn’t. I wear them ALL the time. They’re one of the MOST comfortable boots I own, I love the simple style, they’re easy to take off and on, and the green works with almost everything. Tons of great olive green boot options this winter (this one is the most similar with Dr. Scholl’s comfort and more sizing)…many on sale.

More Walkable Olive Boots

2. Coziest Boots For Super-Cold Days: Stylish UGGs

These warm, cozy UGGs are perfection. I love that they're different from the usual UGG look, but still have all the features of UGGs we adore. Super-warm, super-cozy, super-soft, super comfortable.

At Saks | At Macy’s | At Nordstrom | At Amazon | At Zappos

Oldies but goodies, for sure! These warm, cozy UGGs are perfection. I love that they’re different from the usual UGG look, but still have all the features of UGGs we adore. Super-warm, super-cozy, super-soft, super comfortable. Although there are laces, I tie them loose enough that I can pull the boots off and on without having to retie, which is why they get worn more than these super-cute winter hikers. You have to search for sizing in my exact UGG boots (retailers with stock listed above), but several very similar options below.

More Warm Cozy Boots

3. Best Booties For All Day Walking: Dansko Clog Boots

My love affair with Danskos is strong and steady (especially for all-day walking). Truly, clog boots in general get a HUGE shout-out in this post.

At Zappos | At Nordstrom | At Dansko | Non-Buckle Version at Amazon

Oh, Dansko, of COURSE you’re going to make this list. My love affair with Danskos is strong and steady (especially for all-day walking). Truly, clog boots in general get a HUGE shout-out in this post. For years I’ve worn a higher-heeled clog boot for “dressing up” and a lower-heeled clog boot for day-to-day. I am committed to making them work for pretty much everything, and so many cute options right now that could be worn for many winters to come.

More Cute Clog Boots

4. My Go-to Sneakers For Exercise: On Cloudswift Sneaks

I'm completely on board with everyone's On sneakers obsession. The cool styles, the unique tread, the pretty colors, the focus on comfort...it's all working!

At Nordstrom | At Zappos | At Backcountry

I’m completely on board with everyone’s On sneakers obsession. The cool styles, the unique tread, the pretty colors, the focus on comfort…it’s all working! I needed a new pair of black sneaks this winter and am very happy with my choice. I can easily wear them with denim or joggers for running errands or walking the city, but they’re supportive and comfy enough for true workouts as well. I love a bright-colored playful sneak, but my black ones get worn the most.

More Stylish Atheltic Sneaks

5. My Favorite Shoes For Home: Cozy Birkenstocks 

I wore these cozy Birks all winter last year and am continuing to wear them on the daily this winter as well. They're supportive for walking on hard flooring, and the soft shearling lining that feels amazing on your feet. Huge bonus...plenty of breathing room for toes that don't enjoy being stifled in the house.

At Nordstrom | At Zappos | At Free People

I wore these cozy Birks all winter last year and am continuing to wear them on the daily this winter as well. They’re supportive for walking on hard flooring, and the soft shearling lining that feels amazing on your feet. Huge bonus…plenty of breathing room for toes that don’t enjoy being stifled in the house. These Birks are my ideal house shoe, but I know plenty of readers who love their Vionic house shoes as well as closed-toe cozy Birks options.

More Supportive House Shoes

It’s always fun to hear from you guys about your favorite comfort shoes, so feel free to chime in! Summer/spring comfort shoes are slowly starting to appear as well…any you want me to take a look at?

-Linzi

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