Personally, I’d suggest wearing them with leggings, a long sleeve tee, an oversized puffer vest or coat, and a beanie for a cute, laid-back look.

2. Steve Madden Bettyy Combat Boots

These chunky platform combat boots are perfect for anyone who wants to keep their feet dry this winter, while remaining on-trend. I’d recommend these to someone who lives in a place where the winter weather doesn’t get too terrible. This is because these boots, although definitely waterproof, aren’t particularly warm unless you layer them with thick socks.

For a fun and trendy look, style these boots with a bodysuit, a pair of cropped mom jeans that hit just above the boots’ opening, and a coordinating puffer coat.

3. Ugg Classic Mini II

Click to Buy at Ugg.com

You read that right. Uggs are officially back and we’re once again obsessed.

If you’ve never worn Uggs before, you are definitely missing out. They are perhaps the most comfortable boots on the planet, and they’re super cute as well.

While you definitely can wear Uggs in super cold and snowy climates, we recommend them most for places with mild winters. That’s because, while warm, Uggs are not particularly waterproof and aren’t made to withstand slushy or very wet conditions.

Ugg does sell a special protector spray made to extend the life of your boots, but nothing is going to make them fully waterproof. Just something to keep in mind if you’re investing in these cute and cozy classics!

Related reading: Boots Similar to Uggs: 11 Gorgeous Alternatives to UGG Boots for the Winter

Cute Boots For Moderate Winters

4. Sperry Maritime Suede Boots

How insanely cute are these winter boots from Sperry? Not only are they waterproof but they are super warm thanks to a lining that’s a combination of Thinsulate and fleece.

I would style these boots with black leather leggings, an oversized beige sweater, a puffer, and a plaid scarf for a cute apres-ski kind of look.