8 Boots You’re Definitely Going to Need This Winter

Photos courtesy of each manufacturer.

Ahh, winter in Chicago. The smell of wet wool fills the air, the sky has been the color of tarnished silver for so long you’ve forgotten what the sun looks like and, oh yeah, the ground is covered in wet, icy slop. Sorry UGGs, I love you — but you’re no match for Chicago winter slush. Here are eight pairs of boots that are genuinely up to the job: Whether it’s tromping through a parking lot or scraping off your car, these boots will get it done.

Rag and Bone Moto Rain Boots

Rag and Bone Moto Rain Boots

These fantastically edgy black moto boots are swiftly going to become a cold-weather staple for you. Between the painfully cool metal accents and the ease with which you can pull them on, they have you covered in terms of both comfort and style. Plus, the black textured rubber will keep your feet warm and dry, no matter how much sludge you trudge through. $225, Barneys 

Moncler Blanche Lace-Up Hiker Boot

Moncler Blanche Lace-Up Hiker Boots

These boots are suede, which means you’ll have to waterproof them, but once you do, there’s basically nothing stopping you from climbing Mount Everest (well, okay … maybe not Everest, but definitely Denali). The tough trimmings and thick soles on these boots will keep you well above the snow for this and many winters to come. $615, Neiman Marcus

Sperry Saltwater Misty Boot

Sperry Saltwater Misty Boot

An updated take on the classic “Duck Boot,” these are perfect for rainy winter days. The rubberized toes will keep your feet warm and dry, and there’s no danger of looking schlumpy — between the cable-knit trim and the buckle accent, you’ll be tucking your skinny jeans into these all winter long. $150, Shopbop

Sorel Joan of Arctic Waterproof Cold Weather Lace Up Leather Wedge Booties

Sorel Joan of Arctic Waterproof Cold Weather Lace Up Leather Wedge Booties

We picked this boot partially because of the name, but mostly because winter doesn’t stand a chance against these simultaneously fashionable and durable boots. The grippy rubber sole will keep your feet steady no matter how slippery the sidewalk. These are perfect for a night out when you just can’t justify UGGs but don’t want to risk your feet to frostbite. $250, Bloomingdale’s

UGG Simmens Waterproof Leather Boot

UGG Simmens Waterproof Leather Boot

These truly gorgeous boots are proof that there’s more to UGG than just fuzzy slippers that make you look vaguely duck-footed. Since they’re already waterproofed, you have nothing to worry about and the treaded bottom will keep you solid on icy walks. $190, Zappos

Hunter Boot Original Tall Floral-Print Rain Boot

Hunter Boot Original Tall Floral Print Rain Boot

As fantastic as the original Hunter boots are, these floral-patterned ones are a serious upgrade. Perfect for pairing with tall, cozy socks, these will keep you warm and dry during the innumerable gray and rainy days that span early and late winter in Chicago. Plus, don’t those flowers just cheer you up as soon as you look at them? $175, Neiman Marcus 

Columbia Sportswear Women’s Minx Mid II Omni-Heat Boot

Columbia Minx Mid II Omni-Heat Boot

These are your heavy-duty, time-to-dig-out-the-car, trudging-through-the-Arctic boots. They’re insulated to Saskatchewan and back, completely waterproof and finished with an advanced traction sole for serious winter wear. Plus, with a faux-fur collar and a trendy mukluk-style lacing, they’re pretty darn cute for snow boots. $120, Erehwon

Kate Spade Samira Leather and Faux Fur-Lined Boots

Kate Spade Samira Leather and Faux Fur-Lined Boots

On days when you need to channel your inner goddess, these will help you on your way. We dare you not to feel fabulous strutting your stuff in these cozy-yet-trendy boots, replete with faux fur and fantastic geometric laces. The grippy bottoms and snuggly insides will make you quietly wish for cold weather so you can wear them … and then swiftly take that wish back once February hits. $200, Lord & Taylor


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