A Fashion Girl's Guide To Wearing Winter Boots

The temperatures are frigid, and while snow isn’t necessarily a given as we enter further into climate-change-impacted winters, it’s still fun to fantasize about dressing up in your coziest footwear and trudging through the snow. Winter boots can often lean utilitarian (read: unattractive), but some brands are carving out new space in the field with options that not only work for all weather, but all outfits... but then again, there’s something to be said about wearing the least appropriate snow shoes and going for a bit of drama.

A few trends in outerwear have trickled down to shoes, not least of all fuzzy, shearling boots which we’ve been seeing this fall. There’s also puffer boots, and more people might be wearing the slick style on their feet than their top half this winter. Below, we’ve taken a look at four different outfits (three of which were papped in Aspen, naturally) and shopped out ways to buy into the trend and ensure you’re 10 toes down on fashion this winter, whether you opt for waterproof galoshes or choose to throw caution to the wind and still wear heeled shoes.

High Drama, High Fuzz

This ain’t Texas — it’s Aspen! Everyone leans into the frontier-adjacent style of Kemo Sabe when they decamp to the Colorado ski town, and this Kendall Jenner outfit still holds space in my brain. While some of the shearling boots do have some tread soles and waterproofing, most are just for the look, so make sure you’re not tramping through brown snow in your freshest fuzzy boots.

All Black

Hailey Bieber’s refined minimalism came with her on vacation, where she wore the Loewe boots on everyone’s lips in winter 2023. For winter 2024, carry on the puffer energy with shiny pairs that look akin to everyone’s favorite jacket, or opt for a fashion-y pair of Chelsea boots with lining. As long as they’re not Blundstones, you’ll avoid the “city dweller in winter” stereotype.

Moon Boot Or Nothing

Like Rihanna, I too enjoy a Moon Boot, because it does give off a feeling of walking on marshmallows that nothing else has been able to replicate. They’ve stepped up their fashion game recently, with shearling exteriors and a buzzy Jacquemus collaboration on the way. This is one brand where you can’t go wrong with any option.

When In Doubt, Lace Up

While this EmRata pic was taken before winter is even here, it’s still providing inspiration for those non-weather winter days, and proving that classics are classic for a reason. Timberlands are a mainstay for New Yorkers, and can be dressed up and down. If you’re sick of the tan, try out khaki, or a rogue pink/tomato-red combo that can make any boring sweater/jean combo shine.