20 Tall-Boot Outfit Ideas to Wear Year-Round

The best time of the year is upon us: ahem, boot season. With it comes the prospect of trying something new, whether you’re test-driving a trend or giving your new designer boots a spin around the block. Fall is the perfect time to reboot your wardrobe (quite literally). And while there are so many ways to freshen up your wardrobe, I can’t think of any better way to step into the new season than in the most popular style of the moment: tall boots. 

Since last fall, you couldn’t (and still can’t) scour the runway, scroll through social media, or shop from your favorite retailers without spotting at least a few tall pairs of boots. This style has stuck around for better or worse (depending on how you feel). But if you’re a little dubious about buying into the tall-boot trend, don’t be. Despite common myths about higher boots being harder to wear than ankle booties, I’m here to tell you that the versatility of this style is not to be underestimated. Not only can you find a pair of tall boots that fit your style aesthetic perfectly—there’s everything from chunky lug-sole boots to sleek knee-high boots to trendy moto boots and waders—but also this boot height is easier to style than you think.

To prove that point, I’ve rounded up 20 tall-boot outfit ideas that are ideal for fall (and beyond). Plus, I’ve shopped out some best tall boots at every price point. If you didn’t love this popular fall boot style before, prepare to fall hard. 

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