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.
I can’t think of a better way to sell anyone on taller boots than the ensemble above. It not only features one of the hottest boots of the season (yes, the Balenciaga Tall Cagole Boots) but also is an easy outfit to replicate with pieces you already own. Throw a leather separate of your choosing over a tank and pajama shorts, and you’ll be serving a look.
While the black version of these boots is sold out, the pink version is available for preorder.
Do you know those fall days when it’s still too warm to layer, but you’re pining to wear something fall-adjacent? Enter the ensemble above. A lightweight (or sheer) blouse paired with a miniskirt and boots is perfect for transitional weather.
Giddy up.
One of the benefits of picking a taller pair of boots over ankle boots? It can make any outfit 10 times hotter. Suddenly, a simple tank dress and edgy statement jacket are elevated with a bold pair of boots.
Proof that this trend is smokin’ hot.
What’s another easy way you can style tall boots this fall? Pair them with an oversized button-down and leather trench coat.
Perfect for rainy fall days.
For those of our readers still trying to soak up any remaining warm days, consider this the perfect outfit. Pairing jorts with boots and layered tops is the perfect way to ease yourself into the new season.
Fall is suede-shoe season, so you might as well invest.
Just like tall boots, miniskirts have been having a moment—which makes sense once you see this cute outfit. Pairing tall boots with a pleated miniskirt, button-down, and shrug is the easiest way to embrace both trends without putting your skin fully in the game.
The contrast lug sole on these boots is sending me.
Consider this your reminder that tall boots can work for any season—just see the ensemble above. A fun tube dress can be styled with knee-high boots and a shoulder bag during fall, spring, and even summer.
Who doesn’t love kitten-heel boots?
Any former excuses you may have about taller boots not being “modest” end with this ensemble. A higher pair can suddenly become less risqué styled with a leather midi skirt, a simple T-shirt, and a jean jacket. No risks here, just one great outfit.
She’s classic.
While taller boots can defiantly become staples in your wardrobe (with the proper styling, of course), this style can also be a great way to have fun this fall. Don’t be afraid to opt for a boot in suede or a bold hue and pair it with other fun statement pieces (like a sequin dress and blazer) for a look you’ll want to celebrate.
I dream of these boots daily.
Consider yourself more of a minimalist? Then you’ll want to opt for a more utilitarian style like a riding boot. The great thing about this tall boot style is that it can look good with just about anything, but if you need a little inspiration, start by replicating the look above.
Riding boots never go out of style.
Let’s be candid: We all have our own version of fall daydreams. Whether you dream of cuddling up in a cabin or enjoying the picture-perfect weather in the city, a fun cardigan paired with pleated shorts and boots will fulfill the fantasy.
Investing in neutral boots is never a bad call.
Not convinced quite yet that tall boots are easy to style? Consider the look above as further proof of my case. A matching knit set is elevated by simply slipping into these boots.
Platforms will still be a big trend this fall, so these boots are the perfect purchase.
You don’t just have to wear dresses with taller boots; you just have to be willing to get a little creative (see the look above). Don’t be afraid to tuck in trousers to your boots; it will make your outfit look 10 times cooler.
Pants would look so good tucked into these boots.
The best thing about tall boots is that they can add the perfect pop to any ensemble. But if you want to really stand out, take a cue from the look above, and pair a black dress with snakeskin-print boots.
Yes, yes, yes.
Not to sound like a broken record, but this style is so easy to wear. All you have to do is throw on a sweaterdress, trench coat, and boots, and you’ll look so put together.
You’ll wear these well into the winter.
If you thought wearing these boots was only something you could pull off in fall, think again. Styling skinny jeans underneath your boots and throwing on a heavy shearling coat is an ensemble you’ll want to bookmark for winter.
Hello, boots of my dreams.
I’ll let you in on a little secret: The key to crafting cool outfits is all about mixing and matching statement pieces. Pair your tall boots with a printed skirt or trending jacket, and watch the compliments come in.
Note the chain hardware on these boots.
With weather being more unpredictable than ever, tall boots are the ideal shoes because they can withstand heat, cold, water, and general “what do I wear” qualms. Simply add layers, and you’ll be ready to step out no matter the forecast.
Faux-croc always manages to look so luxe.
Possibly the easiest way to style tall boots is by throwing on a slip dress and blazer. It’s a basic outfit formula, yet the look never fails to be beautiful.
BRB, will be drooling over these buttery-hued boots.
Hopefully by now, you’ve concluded that tall boots are the fall staple. I’ve droned on about how you can shop so many different versions of this boot and style it in various ways, but possibly the strongest case I can leave you with is the outfit above. The best thing about this boot style is that it lends itself well to becoming a staple in your closet not just for this season but for many to come.
Pro tip: Opt for even taller boots to layer under dresses in the winter to keep warm and look chic.
