I used to believe there was no such thing as a chic winter boot. Heavy-duty stompers that can withstand snow and slush and not make me feel like a frumpy outdoorsman in the Arctic? They were a myth on par with the Loch Ness Monster. But then I moved to New York City and saw how the fashion set doesn't let challenging winter weather compromise their shoe integrity—and learned that they actually shop them on Amazon.
A snow squall will be raging outside, and a New York It girl will slip into her favorite boot trend—say, heavy-tread moto boots—and continue bopping around downtown Manhattan. She’ll wake up to an unrelenting downpour, slip into a surprisingly cute pair of rubber rain boots, and still make it to work on time.
My fellow members of the NYC fashion-verse have shown me that brutal winter weather doesn’t mean I have to succumb to four straight months of grumpy gorpcore—all it takes is a bit of extra research to find hard-working, practical boots that incorporate trending touches.
Exhibit A: A New York Fashion Week guest wearing a pair of taxi yellow, lug-sole Chelsea boots on a slushy February day.
Alternatively, you can follow a fashion editor's curated round-up of winter boots that also tick off the top shoe trends—like this one, for example. Ahead, I combed through the best Amazon Prime Big Deal Days of 2025 to find winter boots similar to those I’ve seen in action around NYC.
Keep scrolling to shop 22 surprisingly polished pairs on sale I found hiding in the retailer's shoe sale. The October Prime Day event is only running until October 8, so it's time to get shopping.
The Best Deals We've Found (So Far)
I will always stand by a timeless tall Hunter boot. Worn with slim-fit pants tucked inside or draped under a knit maxi skirt, they're much more versatile than you'd first imagine.
No, these aren't as practical as others on this list, but they're very cute and still worth being considered in my not-so-humble opinion.
The same goes for Hunter's micro-sized Chelsea boots—especially in the ever-popular olive green, which is always a top fall color trend.
A simple Chelsea boot in goes-with-anything black makes for a neutral, grounding touch to any cold-weather look.
In case you're uninitiated, Uggs have staged a comeback, landing on fashion runways and in It girls' closets. Their status as a great winter shoe remains untouched.
I would be remiss to not also include these chunkier Ugg boots in caramel.
These distressed brown leather knee-high boots are a smart tie in into the boho fashion revival.
At 76 percent off, these AllSaints Chelsea boots are perhaps the best deal I can vouch for on this list.
Considering I've made a personal vow not to buy any more black boots, I'm eyeing these crisp white Chelsea boots from Sorel, a brand known for storm-proof footwear.
Step into the moto boot trend without worrying you'll slip on ice.
Add this shearling bootie to your winter wardrobe for extra, Teddy Bear-esque coziness.
Yes, these lace-up Sorel booties don't immediately read as chic. But with tights and a mini dress—stay with me—they can be a tougher element to balance out more girlish elements.
Ugg boots don't always mean suede and shearling. These tall and timeless Chelsea boots are a breath of fresh air.
The same approach applies to a classic Doc Martens combat boot. With a dark knit dress and a simple, no-fuss wool coat, they'll become part of a grown-up yet '90s grunge combination.
Rich chocolate brown, soft suede, and on sale. Check, check, check.
Maybe don't wear these during an active snow storm. But they're still worth considering as a top contender in your winter shoe rotation.
It's not actually surprising that suede boots are a fall 2025 trend—the brushed textile spikes in popularity every autumn. But just because it's predictable doesn't make it any less worthwhile.
I can see myself wearing these brown leather knee-highs with an ivory sweater, plaid mini skirt, and a pair of burgundy tights—in my not so humble opinion, hosiery is an under-utilized accessory.
Simple: I see Coach, and I'm already intrigued. Given Coach's reputation with It bags, I'm automatically inclined to shop.
Some people might have moved on from Beyoncé's Cowboy Carter tour. I, for one, have not, and will keep channeling a yeehaw spirit for winter '25.
Again, I'm trying to curb my penchant for black boots. These tan Vince Camuto knee-high boots do the rick.
A tall black boot will rarely disappoint.
