20 Of The Chicest & Most Affordable Thigh-High Boots For Fall

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It's that time of the year again. The hunt for the perfect cold weather shoes is officially on, so prepare to pull out those bills you've been saving because thigh-high boots for fall 2019 are so good you'll definitely want more than one pair. If you're afraid of the shoe, don't be; over-the-knee boots have become synonymous with cool girl autumnal style over the past handful of years, meaning there are infinite inspiration images out there that can show you exactly how to wear them. Pull your favorite snaps up on Instagram, decide which boot textures and silhouettes will gel with your wardrobe the most seamlessly, and prepare a shopping list stat.

From pointy-toed cowboy styles to straightforward black iterations, the selection of thigh-high boots is endless. Red, camel, snakeskin, silver, suede, patent, zip-up, pull-on — no matter what kind of footwear you typically rock, there will be a boot that will strike your fancy. Below, you'll find 20 of the coolest (and most affordable!) pairs that are currently on the market. Take time to peruse them all, see which ones you drool over the most, and add them to your cart. It never hurts to have both a flat and heeled version of a boot style, so if you can swing it you might want to snag two pairs.

What A Snake

Imagine rocking these snakeskin boots with a black miniskirt and long sleeve crop top — it's the fall going out look of my dreams.

Out West

The cowboy-inspired trend isn't going anywhere anytime soon, so why not snag a pair of thigh high boots featuring a pointed toe, block heel, and Western stitching?

All Tied Up

You can never have too many options when it comes to black boots, so here's another pair of straightforward black thigh-highs — these feature a tie at the back.

Heel Yes!

A chunky heel is always my best friend (stilettos have it out for me), so this pair of black thigh-high boots needs to join my wardrobe stat.

Touch The Sky

Love a chunky platform? These vegan leather boots boast a '70s appeal that's going to be hard for you to resist.

Desert Dreaming

I'd pair these gorgeous suede leather boots with a flowy floral maxi dress and wide-brimmed hat. The ultimate breezy fall ensemble.


Who knew Hot Topic would come through with such cool chunky lace-up boots in 2019? Pair these with a vintage '90s dress and you've got yourself an ace grunge look.

Feeling Grey

Between their silvery grey hue and metallic sheen, these boots feel like they're straight out of a fairytale.

Hocus Pocus

These boots are part Gucci, part Fendi, part paper bag shorts in footwear form. Oh, and they're all the way cool.

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