Wondering How to Wear Ankle Boots With Skinny Jeans? These 5 Outfits Are So Easy to Recreate

editor@purewow.com (PureWow)
·3 mins read

Just like peanut butter and jelly, base coat and top coat and Sarah Paulson and complex female characters, skinny jeans and ankle boots are a duo that just makes sense. If you’re not entirely sure how to style this easy outfit combo, scroll down for the exact kinds of ankle boots you should be pairing with your go-to skinnies.

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1. Combat Boots

There’s a reason why skinny jeans are an off-duty model favorite: They’re just so damn easy to throw on. They also pair well with flat boots, like the combat style pictured here. Tuck a pair of dark skinnies into your lace-up kicks for a cool, streamlined look. Because your jeans and pants are slim-fit, you can go a little bigger, proportion-wise up top, with a bold cropped bomber or puffer jacket.

Shop Combat Boots

Dr. Martens $150

Sam Edelman $180

Karl Lagerfeld Paris $199

Allsaints $348

2. Kitten-Heel Boots

The pairing of black jeans with black boots gives the illusion of endless legs (because you kinda can’t tell where your pants end and your boots start). For even more leg-lengthening, opt for boots with a pointed toe, which extends the line of your legs just a bit further. This might not be the trendiest look, but it sure is timeless, meaning you can wear it with tops, jackets and accessories that push the limits. Go on, test out that XL belt or the voluminous puff-sleeve you’ve been eyeing.

Shop Kitten Heel Boots

Circus by Sam Edelman $59

Jewel Badgley Mischka $110

Charles by Charles David $119

Veronica Beard $495

3. Chelsea Boots

If you’re wearing skinny jeans with flat boots, like this Chelsea style, you want the pants to end right where the boots begin, or even a few centimeters higher. While the pants-tucked-into-boots approach looks fab with dark skinnies and black boots (refer to the combat photo up top), a hint of ankle can do a world of good when your jeans and shoes are in contrasting colors.

Shop Chelsea Boots

Caslon $100

Ugg $150

Blundstone Footwear $200

Aquatalia $450

4. Printed Boots

See what we mean about a hint of ankle? Even though leopard is a neutral at this point, it’s still a sharp contrast against basic black and white. Also, keep in mind that if your ankle boots are done up in a bold pattern (which we wholeheartedly encourage), the rest of your ensemble should be on the simple side, with clean lines, neutral colors and not a whole lot of embellishment—lest you take attention away from those killer shoes.

Shop Printed Boots

Jessica Simpson $89

Charles by Charles David $119

Chinese Laundry $120

Marc Fisher LTD $210

5. Cowboy Boots

Because cowboy boots often have a pointed silhouette, think of these bad boys like the pointy-toe kitten heels from earlier and wear them with skinny jeans in a similar shade. See how it looks like this stylish gal’s shoes and pants are one? That’s the vibe we’re going for. Note that if your cowboy boots hit higher on your calf, you’re going to want to tuck your jeans into them. With a shorter style, however, a slim-fit pant can slide right over the top without any unseemly bunching underneath.

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Shop Cowboy Boots

Bella Vita $120

Fly London $300

Ganni $475

Isabel Marant $770