20 Ways to Wear Boots This Fall

By 11 October 2016


In preparation for fall and the gorgeous, cozy fall outfits, I wanted to share with you 20 stylish ways to wear boots. (Fall, the best time of the year!) The cute outfit possibilities with boots are endless and this should give you plenty of outfit inspiration for the fall and winter season.

I’ve made this post a roundup of my favorite boot outfits that I’ve worn on the blog; everything from how to wear ankle boots to wearing booties with jeans.

Boots are my preferred footwear during the fall. With the so many boots options available—flat, over-the-knee, heeled, wedge, pointed toe, ankle—there is a boot to go with every outfit and occasion. You can wear a dress with boots, jeans with boots, and even ankle boots with trousers.

Depending on your style and your personal preference, a classic black or brown riding boot might just be the only boot you need. But if you’re a boot enthusiast, like I am, then you’ll want to wear flat embellished ankle boots, heeled ankle boots in black and brown, some furry boots for the snow, and black suede over-the-knee boots.

Below you’ll find 20 example outfits that are paired with boots with an explanation of why each outfit works. If you want to see more photos of the outfit just click on the image or the link in the outfit title. By clicking, you’ll be directed to the original outfit post.

There are a lot of places you can buy a nice pair of boots. The boots I own came from a variety of brands.


I love to buy brown boots or booties from Sole Society. They have many affordable options and new styles every year. Many of them are under $100, so they don’t break your boot budget, and they also last several years.

My classic riding boots are from Ariat. Their quality is exceptional, and they last a very long time. I like classic-style riding boots in black or brown with burgundy accents. You can see two ways I styled riding boots below.

For snow boots, I turn to Ugg. They are durable, well made, and they have some very fun options.

For some cute and trendy fashion boots, I like Naughty Monkey. They have a good variety of styles that are under $100, so if I want a fun pair of boots that are embellished or have fringe accents I like looking at what they have available. The embellished ankle boots and the black flat riding boots I’m wearing in outfits 5 and 8 are from Naughty Monkey.

For rugged outdoorsy boots that you would wear, say to a pumpkin patch, like the boots I’m wearing in outfit 12, I like CAT footwear. CAT initially just made work shoes, so you know these are durable.

For all other boot styles, I usually peruse Nordstrom. They have a ton of brands and every style you would want.


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