Wondering How to Wear Ankle Boots With Skinny Jeans? Just Follow These Style Rules and You’ll Be Good to Go

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.

Pairing sleek booties with slimming jeans gives the illusion of mile-long legs (especially if you opt for a monochromatic duo. 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.

Remember, 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 above), a hint of ankle can do a world of good when your jeans and shoes are in contrasting colors.

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.

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.

Now that you know which styles pair best with your beloved skinnies, let’s look at your outfit as a whole. Here, five foolproof ankle-boot-and-skinny-jeans outfits to mentally bookmark for days when you’re in a rush.

Any jeans with volume—boyfriend, wide-leg, flares—tend to work best with some kind of heel. Skinny jeans, on the other hand, at at their best with flat style or low heel to help your legs look long and lean but not like toothpicks. Continue the balancing act with a sweater or blouse that hits at mid-hip or a little lower and a jacket that ends a few inches above that. (P.S., mixing a longer top with a shorter jacket is a great layering trick no matter what bottoms you’re rocking that won’t add any unnecessary bulk.)

You’re doing this all for the booties, so make sure your jeans are the proper length to show ’em off. A good rule of thumb: Have your denim hit either right at the top of your boot or about an inch above the ankle.

If said hemlines are too long, don’t be afraid to roll the cuffs of your skinny jeans. (Yep, just like you would your boyfriend jeans.) It’s a better option than letting them pool and bunch awkwardly. Don’t be afraid to play around with the size of the folds to see what looks best. You want something that doesn’t jut out too much, but one large high cuff can cut your calf off in a weird way.

If you're having trouble deciding out which denim wash will look best with your new favorite boots, we have a simple solution: Go monochromatic (at least from the waist down). Obviously, this works best with black-on-black, but don’t be afraid to pair white with white or even dark-wash denim with navy booties.

Black or dark-blue jeggings can look super flattering, but we think white jeans look best when they aren’t skin tight. That doesn’t mean you have to stick solely to boyfriend, straight- or wide-leg styles, just opt for a skinny that fits a little looser.