Why We Love Winter Boots—And How We Wear Them

Waking up this week to a few frosty days in a row reminds me that a change is coming. It’s time to unearth my winter coat from where it’s hiding under my bed, and quickly finish knitting the new cozy scarf I’ve been working on. It’s also time to figure out what I’ll put on my feet when cold days arrive. I used to be afraid of winter, I never really saw it as a stylish season, particularly when it came to footwear. Finally, I stopped thinking of winter boots as big, awkward things you just wear to the grocery store and started viewing them as an important part of my wardrobe. I think it had something to do with being tired of cold, wet feet! Winter dressing has been a lot more fun ever since. Here’s how I wear them:

how to wear winter boots

1. With leggings or slim pants, tucked into boots (I like this with tall-ish boots, but it looks cute with short boots, too!).

Conquest Weather Boot, Sweater Leggings.

how to wear winter boots

2. With straight-leg jeans, scrunching or cuffing the denim above the boot (best with shorter winter boots).

1964 Premium Weather Boot, Vegan Leather Trim Skinny Jeans.

how to wear winter boots

3. With a maxi skirt and leggings or thick socks underneath!

Joan of Arctic Boot, Lily Shirred Maxi Skirt.

These days, I not only love winter boots, but I also have a hard time narrowing down my choice to just one pair. The boots shown here are definitely three of my favorites. What are you wearing this winter?

Joan Of Arctic Boot, Conquest Weather Boot, and 1964 Premium Weather Boot.


  1. Dear Jessica and Sweet Pea, If you’re looking for a little outfit inspiration, you got it! Check out three ways we wear our winter boots above.

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