I’m just going to come right out and say it: Uncovering an actually comfortable pair of shoes is easier said than done. You've probably tested out a range of silhouettes over the years that have seemed strong in theory, but found that despite "comfy-feeling” qualities like a flat sole, the shoes have ultimately just ended up creating the same blisters that come with tricky sky-high heels.
My fellow WWW editors share the same sentiment but have also tested out such a wide range of shoes over the years (you know, that fashion editor life) that they’ve actually managed to uncover a few winter shoes that aren’t that painful. Lucky for us, they’re sharing their must-have boots below. Keep scrolling to shop the most comfortable footwear picks of the season—you may just find your new wear-everywhere style.
"I lived in my Docs last winter and they were so comfortable—even for walking around all day here in NYC. I'll definitely be bringing them back this year."
"Believe it or not, it does get cold in Los Angeles. These boots are ultra-warm and save my feet when I absolutely need to run outside in the rain to feed my overpriced latte addiction. I love that these are furry, all-black, and have an on-trend rugged sole."
"I think it speaks volumes when you can wear the same pair of shoes from morning 'til night and still reach to put them on the next day. (I don't know about you, but I find it impossible to wear uncomfortable shoes two days in a row.) I added these basic ankle boots to my arsenal recently, and I've never looked back. Apart from being one of the most versatile shoes I now own, they're remarkably well-designed (read: comfortable) considering their under-$200 price tag."
"As a fashion editor, I've tried on a lot of boots in my day, and I swear I have never slipped my feet into something more comfortable than a pair of Paige shoes. It's like there's a tiny foot mattress in each one. Not to mention the quality is on par with ultra-expensive designer pairs. If you do a lot of walking or standing, snag a pair of these for winter and don't look back."
"The actual & Other Stories boots I own are from three years ago, but these are very similar, and I trust they're just as comfortable as mine. Aside from the fact that the brand makes shoes that hold up well years later, I love that these are so simple and easy to wear with everything."
"These knee-high boots are truly one of the most comfortable pairs of shoes I own—one of many reasons I'm wearing them on repeat right now."
"I've been wearing these boots a lot lately and even with just thin socks on, I've had zero discomfort. (Bonus: They're very on-trend yet very classic.) Highly recommend!"
"I've been wearing these buttery soft ankle boots on repeat this season—they're made from 100% Italian Nappa leather and are insanely comfortable and supple. The heel is the perfect height to walk comfortably in while still looking altogether polished."
"I've had a pair of classic Chelsea boots from Kenneth Cole in my rotation for a few years. While mine have a lower heel, it's the slip-on nature and wider toe box that makes them especially comfortable."
Shop more boots:
Reviewers actually rave about how comfortable these boots are with no "hot spots” where rubbing occurs.
The stacked heel and supportive buckle strap gives this silhouette extra cushioning.
Described as "perfect boots” by a customer in the review section, these are not only gorgeous but comfortable for a more practical winter shoe choice.
The low, lug sole brings an extra dose of comfort to these classic black boots.
It’s the elastic panels that give these lower-heeled boots that desirable ease.
If you’re looking for a block-heel statement boot to stay comfy for a night out, these will do the trick.
The beauty of these comfortable stunners is that they’re actually waterproof to tackle everything Mother Nature throws our way.
Next, check out the most comfortable shoes out there for city girls.
-
Katie Holmes Is Already Wearing the Boho Boot Color Trend Fashion People Everywhere Will Wear This FallNot once, but twice.
-
Leopard Print Is Fine, But This Is the Unexpected Shoe Print Fashion People Are Already Wearing on RepeatControversial yet chic.
-
Whenever I'm in Paris, I See This Boot Trend Styled With Minidresses in Every Vintage Shop and Local BistroSorry, ankle boots, but it's not you.
-
Everyone in Los Angeles Knows This Shoe Trend Makes Denim Shorts Look Way CoolerDenim shorts never looked so good.
-
Spotted at Wimbledon: The Anti-Summer Shoe Trend You Don't Usually See in the StandsNever too hot for these.
-
The $140 Boots London Fashion Girls Take Out of Storage Every Summer to Wear With Shorts and DressesFrom Kate Moss to Daisy Edgar-Jones.
-
Stop With the Ankle Boots—Miniskirts Should Only Be Worn Like *This* in 2025Period.
-
The Unexpected Shoe Style Fashion People Are Reaching For This SummerHere are seven ways to wear it.
