15 Foolproof Tall Boot Outfit Formulas for Dresses and Skirts You'll Want to Try This Week
These boots were made for walking...
We've finally left sandal season behind, which means it’s time to bring your tall boots out of retirement. And while winter does call for layering, your outfits don’t have to feel stuffy. Listen, I know how easy it is to reach for a sweater and jeans, but why not kick things up a notch and try wearing those skirts and dresses you've been investing in all year long?
The best way to get extra mileage out of your wardrobe is by getting creative. Try layering your going-out top over a balloon sleeve dress, elevating a normal sweater dress with a pair of polished croc boots, or mix textures and leathers for a look that's anything but average. And in case you need some visual inspo, I've rounded up 15 foolproof tall boot outfit ideas that pair nicely with leather skirts, mini sequin dresses, silk midis, and more. They're all so chic, and best of all, many of these looks offer more coverage so they're totally appropriate to wear to work and out past five.
Read on for some instant outfit ideas...
A Rugby Shirt Dress
Not only does an oversized rugby shirt feel like the ultimate lazy outfit hack, but it's cute and preppy, too. Match your tall cognac boots to your crossbody bag for extra sizzle à la Taylor Swift.
A Layered Black Top + Black Boots
Ah yes, the classic going-out top and thigh-high boots combo, a tale as old as time. To make the look a little more office-appropriate, try layering your tube top over a balloon-sleeve dress. It pulls everything together by playing with volume.
A Playful Patterned Dress + Slouchy Boots
Toughen up a playful dress by adding embossed leather boots to the mix. It's an unexpected pairing that feels refreshing and adventurous enough to wear out to dinner (or even your next big work meeting).
Mix Textures
By pairing a chocolate leather skirt with slouchy coffee-toned boots, you add a little visual drama to a safer outfit. This look works beautifully for everything from an office day to Thanksgiving dinner with the family, plus the minty blue + brown pairing is seriously delicious.
A Faux Fur Coat + Statement Boots
I believe that more is more, so of course you should wear your fluffiest faux fur coat, silk button down, micro mini skirt, and tallest embroidered boots in the same outfit. You'll be warmer thanks to the higher boots even if you're showing a little thigh.
Double Up On Burgundy
Being matchy-matchy is the quickest hack to getting out the door on time. Pick a couple colors to center your outfit around, like burgundy and blue, and then grab a polo, a sweater, and some matching boots in those shades for that effortlessly capital-F Fashion look.
A Canadian Tuxedo
Yes, a Canadian tuxedo can absolutely be gussied up. In fact, it looks downright dressy when you add structured black boots and a clutch to the mix.
A Slip Dress + Patent Boots
A slinky slip feels unexpected and cool when paired with a pair of patent boots. Both textures feel so luxe. Layer on a belt and a denim blazer for extra coverage and styling.
Sequin Mini Skirt + Silver Boots
While a super sparkly mini may not seem like it would be a good match for some thigh-high silver boots, I beg to differ. The monochromatic effect (amplified when you add in a heather gray sweatshirt!) does all the talking.
A Leather Moto Jacket + Denim Skirt
Think of your denim skirt as the cool swap for everyday denim jeans. Go for a skirt that hits just above the knee to show off your best cherry red boots and add a leather jacket for extra oomph.
All-Over Red + Cheetah Print Boots
Take a walk on the wild side and pair fiery red with leopard print for a daring combo. Don't be shy to commit and wear a coat in the same shade of red (you're sure to be remembered in this striking look).
Suede on Suede
Suede is a deliciously luxe material that shines on its own, but it’s even more striking when layered with... yep, more suede. Try a suede dress or mini skirt paired with a leather bomber jacket and a structured black bag for a polished finish
A Statment Coat + Black Dress
Jazz up an all-black work dress with a colorful statement coat and the tallest pair of boots you own. They bring all the drama while still being safe to wear to work—so no need to run home to change before happy hour drinks.
A Poncho + Rainboots
A waterproof poncho and tall leather boots are a match made in heaven. Not only do they keep you protected from the elements, but they also ensure you’ll look effortlessly chic even if you get caught in a downpour.
A White Jacket + Turtleneck Dress
This look proves that a turtleneck dress can be dolled up, especially when you add a chic, belted white jacket and tall leather mustard boots.
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