Sharing a round up of my top boot and bootie picks for the cooler months ahead! I’ve tried to keep these mostly under $100. Those that are over are definitely staples in my closet and ones I’ve had or plan to have for years! And, like I mentioned on stories earlier this week, I do plan to do a huge winter gear round up (coats, boots, hats, gloves etc) soon. So, I’ve kept most of these to just regular boots/booties.

A ton of these boots are on sale this weekend so definitely take advantage. A few favorites like my tall brown boots, sneaker booties, and studded booties are all on sale! Also eyeing up these fur-line wedge sneaker booties. Think I *need* them – ha! And, ICYMI, DSW is having 25% off all booties with code COOLBOOTS. My faves are all on this page.

Rounded up my top picks in the collage below and sharing a ton more at the bottom of the post!