The Fall Boot Guide

The 2018 Fall Boot Guide

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Boots are undoubtedly my favorite type of shoe because – you guessed it – they’re a staple item for my favorite season. Packing for Vermont last week got me thinking about which pairs of fall boots I love most. There are several I purchased recently, like my used Stuart Weitzman midlands (similar under $100 here), my knee-high Tory Burch pair. And, of course, there are pairs I found years ago and still treasure. I think having one pair of booties, knee-high boots, and over-the-knee boots on hand lays the foundation for a versatile cold weather shoe selection for virtually any outfit. With that in mind, keep reading for the best of boots in each category at various price points.

Above: Hinge booties, old (similar under $100 here)


Booties are my go-to for casual days in my office and around town. I choose low shaft booties for ankle length skinny jeans, but I love a higher shaft for cropped jeans, skirts, and dresses. This season I’ve been loving the variety of color brands are putting out. I’ve had my eye on these burgundy ones as well as this blue pair for a while now. If you have to choose one pair on a budget, however, I’d go with these taupe booties under $100.

Above: Tory Burch Knee-High Boots (50% off here)

Knee-High Boots

Knee-highs are my favorite of the three types because, to me, they scream cold weather. I usually pair them with skinny jeans and a chunky sweater, but they’d look great with a tweed or suede mini skirt and a boyfriend blazer, too. This Sam Edelman pair comes in a light neutral I love, and I think these brown leather boots under $200 look just like the Aquazurra Brera 85s

Above: Over-the-Knee Boots (color discontinued, similar under $100 here and here)

Over-The-Knee Boots

I picked up a used pair of Stuart Weitzman over-the-knee boots earlier this season, and I anticipate that they’ll be my most worn. If you don’t feel ready to invest in a designer boot, this pair looks incredibly similar for the price. I love the moderate heel on mine, but a higher heel like the one on these Marc Fishers makes a statement and elongates your legs. Plus, what’s more fall than an oversized turtleneck, skinny jeans, and over-the-knee suede boots? 

What’s your favorite pair? I’d love to know in the comments. Be sure to follow along on Instagram and Pinterest for more fall style inspiration.