The Best Ankle Boot & Jean Pairings, Period

When we're putting together an outfit, most of our attention is devoted to the top-and-bottom combo. If it's a special occasion — or we happen to be #feelingourselves on any given Tuesday — the other components will get the same love and care. The rest of the time, though, we kind of just...wing it. Little black booties and flat leather sandals can do us no wrong (well, usually), and our oversize tote swoops in for the win. But, during the fall, the lower half of our #OOTD warrants a little more attention, seeing as the top half will be buried under some form of outerwear 90% of the time. Luckily, our ankle boot and denim game is looking mighty strong this season, and it's ready to seize the spotlight. To get the ball rolling, we dreamed up the best jean-and-shoe pairings that'll make you reconsider how you go about planning your outfits.
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Cropped, then cuffed: These dark-wash jeans give your ankle boots prime real estate. So, eschew classic black in favor of a patterned, textured style. Snakeskin's coming up strong this season; luckily, you don't always have to pay a premium to get the look.
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How much do you miss the '90s? High-waisted raw denim and crisp, white sneaker boots much? Because we're there.
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The cropped boot-cut hem on these H&M jeans is meant to show off a sleek shoe, so don't skimp with this pairing. We like a zip-up leather option with a polished black finish to play off the gray denim. The stacked heel will lengthen your silhouette, as well.
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When your jeans are the main event, keep the other elements of your #OOTD cool and subdued. These cinched-ankle boots are not only incredibly practical (the elastic around the opening ensures they stay put), but the deep navy makes for a subtle colorblock.

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Dip-dyed hems are all the rage now, calling all the more attention to your ankles. A flat shoe keeps the focus on the standout denim. The hardware and elaborate closure out front makes these booties stand out on their own, too.
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That moment when your fallback outfit is the most elegant pairing in your closet. The rich, colorblocked suede on these heeled boots pops against the uniform white of the straight-leg, straight-hem jeans.
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An embellished pant can be one of those emotional purchases you make because it's so darn good, it makes you so darn happy, and you're bound to find a reason to wear it...someday. But, it's an opportunity for clever accessorizing: The gold buckle on these fringed leather boots plays off the mixed-metal studs on the boyfriend jean — a choice that will speak volumes about your attention to detail.
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Embrace the kooky: Double up on fray, and make sure you keep those shiny patent boots squeaky clean for maximum impact.
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The slightly faded gray wash on these skinny jeans shifts the focus to the rich texture on your toes. The "one neutral, one statement" formula never fails.
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Keep the casual vibes of a boxy boyfriend silhouette going with a low-heeled zip-up boot. From the front, it looks like your run-of-the-mill Little Black Boot. But, it features graphic calf-hair paneling for a measured walk on the wild side.

Steven Alan jeans.
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Cash in on the fringe benefits of the '70s revival, which include high-waisted, straight-legged jeans with a kick at the ankle for a mini flare, and tan suede booties that are equal parts elegant and retro.
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Give those pearls a whirl — that's certainly one way to dress up your slouchy denim. Since this boyfriend jean wears a strand of pearls all the way down the leg, there's little need for embellishment. That's where sleek leather boots come in, with a look-at-me chunky heel that'll add a spring to any step.

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The speckled-paint coating and skinny fit of these jeans makes it easy to forget that they're denim. Throw a bright, buckled high heel into the mix, and the illusion will be much harder to break.
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This shoe blends the comfort and convenience of moccasins with the sophistication and put-together finish of ankle boots. What better way to dress up your coziest weekend jeans?

J.Crew Pants.
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Tap into your grunge side (there must be some of that left over from the '90s) with fashion's put-together take on chunky platform boots. Paired with just-destroyed-enough boyfriend jeans, they nail the whole "minimum effort, maximum cool" thing.
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Suede boots and wide-legged denim — a match made in throwback heaven.

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