14 Essential Winter Shoes You Need in Your Closet

In this post, I’m sharing a round-up of my favorite winter shoes. There’s something here for everyone from Chelsea Boots to Chunky Loafers to Waterproof Snow Boots. So, whether you have a specific style in mind or you’re just here to shop, welcome to my favorite winter shoes round-up. I hope you find something you love!

I’m an accessory girl – through and through and one of my favorite accessories has always been shoes. In my world, with the right shoes and the right handbag, you can tie any look together. And as a New Yorker, I know the importance of having good shoes in the winter. 

Winter can be a tricky time of year for footwear. You want something stylish but also practical. And trust me, there’s nothing worse than cold, wet feet in a cold New York winter. So without further ado, let’s shop! 

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14 Essential Winter Shoes You Need in Your Closet

Black Leather Ankle Boots

The Cole Haan Catlyn Bootie is the perfect blend of timeless style and everyday comfort. You can wear this sleek pair of ankle boots with skinny jeans, skirts, or dress pants. With a cushioned footbed and sturdy block heels, they’re comfortable to wear all day – making them a great option for the office or errands. 

If you’re looking for an affordable, everyday pair of boots for 2025 – look no further! The Catlyn Bootie is for you.

Chelsea Boot

This stylish pair of shoes goes with literally everything in your wardrobe. If you only invest in one pair of new shoes from this winter shoes round up, I recommend these. You’ll find yourself pulling them out nearly every day. 

Made with a chunky lug sole and stretchy side panels, this pair of boots is as practical as it is stylish. Dress them up or down – your Chelsea Boots are ready for anything!

Knee High Boots

If you’re looking for a pair of shoes that’s going to last for years to come – the Sylvia from Sam Edelman is a great option. The Sam Edelman brand focuses on quality and their shoes are designed for lasting comfort and style. I’ve loved every pair of shoes I’ve gotten from them. 

This pair of knee-high boots will elevate your looks this winter. For me, it’s an essential pair of winter boots (especially as a tall girlie!). I can style these boots with jeans, my longer coats, or dresses for endless and effortless looks all winter long.

Combat Boots

Unlike other classic boots, combat boots are inherently edgy, which means they’ve come in and out of style over the years. And while they’re edgy, they’re also totally wearable.

I personally love that combat boots add a twist to your otherwise more dressy and chic looks. Style them with a slip skirt or mini dress—or with a pair of jeans and a chunky sweater.

Suede Ankle Boots

Sometimes, you just need a classic pair of boots to make even your most casual outfits look more classic and chic. That’s what I love about the Saige Bootie from Sam Edelman.

With a thin heel and pointed toe, this is a sexy pair of boots that will complement your winter brunches with the girls and date nights out with your partner.

Casual Booties

Let’s face it, it wouldn’t be a winter shoes round-up without a classic pair of UGG booties. Girls, some days you just need to throw on the most comfortable pair of shoes you own. And that will be this pair of UGG booties. I also love that UGG is such a classic style.

You can put together the perfect ‘running around town’ outfit or ‘heading into pilates’ look with this cute pair of winter shoes.

Winter Hiking Boots

This is quite possibly the most beautiful pair of hiking boots I’ve ever seen. They’re the perfect mix between classic Chelsea boots and upscale combat boots.

I would almost be afraid to take them out for fear of ruining them! Stuart Weitzman is another trusted brand when it comes to quality-designed shoes. With padding around the ankle for added comfort and support, this stylish pair of boots is one of a kind. 

Waterproof Snow Boots

If you’re a New York girlie like me, or you live anywhere that gets cold in the winter, you need to run and pick up a pair of these stylish waterproof snow boots from Sorel.

Gone are the days of bulky and ugly snow boots. Trust me, this is an essential pair of winter shoes for any city girl.

Chunky Loafers

I love loafers, but they’re not the most winter-friendly pair of shoes. More often than not, they leave your feet feeling cold and wet. That is until now!

This pair of loafers features a lug sole designed to be worn all year. Naturalizer designs them – and what I love about this brand is that it was started in 1927 specifically for women. So if anyone knows women’s shoes, it’s going to be them.

Pointed-Toe Booties

The Yanara Bootie from Marc Fisher is stylish with everyday wear. Designed with a sleek pointed toe and a chic block heel, this bootie adds instant polish to any outfit, which is why I had to include it in this winter shoes round up.

They’re made from soft leather and have a side-zipper closure for easy wearing. I found these boots to be comfortable for all day every year, making them perfect for work, weekends, and everything in between.

Heeled Sock Boots

This is probably the chicest pair of boots on this winter shoes round-up. They feature a squared-off cap toe and flare heel for a glamorous, statement-making bootie. Paired perfectly with skirts, dresses, and flare jeans, this pair of booties is surprisingly comfortable.

Riding Boots

If you’re looking for a pair of winter shoes that’s more unique, I highly recommend riding boots. I recently invested in a pair of riding boots and I’ve been having so much fun styling them.

These boots from Tory Burch are an amazing quality – and they look even better in person. For something a bit different this winter, pick up a pair of these gorgeous boots.

Shearling-Lined Mules

With the trend of quiet luxury on the rise, this pair of loafers says, “I woke up like this” (but make it designer). They’re the iconic loafer silhouette that you know and love, elevated with plush shearling lining that’s like a hug for your feet.

Of course, they’ve been created with Gucci’s attention to detail and they scream sophistication. Style them with cropped jeans, tailored trousers, or even a luxe midi skirt. 

Trust me, once you slip these on, you’ll never want to take them off.

Warm Slippers

There is nothing better than coming home after a long, cold day and slipping into a comfortable pair of slippers. Slippers are big in my home – and these UGGs are a classic for a reason.

I’ve owned multiple pairs of these slippers over the years, and if something happened to my current pair, I would buy the exact same pair again.

No matter where you live, or what your style is – I hope you found your new favorite pair of winter shoes in this round-up. From the classic to unique styles, and everything in between, these are the shoes you’ll see me styling all winter long (and well into Spring!). 

If you need help with styling this year, I have plenty of free resources to help you look and feel your best every day. This blog is full of outfit inspiration and product round-ups from winter to spring and summer. 

I also have a free guide to help you design the ultimate Classic Capsule Wardrobe. Having a classic capsule wardrobe can help reduce outfit fatigue, trend-chasing, and overbuying. Instead, fill your closet with classic staples that make beautiful outfits all year-long. Download the guide for free today. 

Lastly, make sure to follow me on Pinterest (@basiarestrepo) for the latest trends, Instagram (@stylewithbasia) for daily outfit inspiration and subscribe on YouTube for more in-depth reviews, closet tips, and try-on hauls. 

As always, thank you for being here! Thank you for shopping for the styles and pieces that I share – your support means the world to me. Happy shopping!