How to Wear Boots with Jeans

Styling Ankle Boots

Choose ankle boots that end 2 inches (5.1 cm) above your ankle. This is the thinnest part of your leg, which you want to show off to keep your silhouette proportionate. If the boots cut you off any higher than a couple of inches above your ankle, they can make you look shorter and stockier.

Cuff tapered jeans above a pair of ankle boots to show them off. To cuff your jeans, fold them up about 2 inches (5.1 cm), then roll them once more. This should create a little space between your hem and the boots, letting you showcase your boots and creating a proportionate silhouette. If you don’t like the rolled hem look, you can roll them inwardly or opt for a cropped pair instead. To balance out a pair of baggier pants, such as boyfriend jeans, use the cuffed method and throw on a pair of heeled ankle boots for a little extra height.

Wear black skinny jeans and black ankle boots for a monochromatic look. This creates a seamless silhouette that makes your legs appear longer and leaner. Make sure to choose a pair of fitted black pants that hug your legs and disappear into the boots. A little heel on the boots also enhances the leg-lengthening effect. For example, you could wear a chunky black and white striped sweater, a pair of black skinny jeans, and black leather ankle boots.

Pair Chelsea boots with distressed straight-leg denim for a casual outfit. The smooth, fitted silhouette of the Chelsea boots contrast nicely with loose, distressed denim. Go for a pair of boots with a low heel to keep the outfit relaxed and casual, and pull up the cuffs of the jeans to show the tops of the boots. Add a white T-shirt and bomber jacket for a relaxed daytime outfit. You could also style a more sophisticated version of this look with a slouchy blazer and button-down shirt.

Wearing Mid-Height Boots

Put biker boots with dark wash skinny jeans for a casual, edgy look. The smooth, fitted jeans pair well with the chunky boots, and the dark wash adds a sleek, seamless effect. Tuck the hems of your skinny jeans into the slouchy tops of the biker boots and finish the look with a simple, classic top. For example, you could dress the look up slightly with a loose black knit turtleneck and a faux fur vest. You could also dress down the outfit by pairing it with a plain black or grey T-shirt and an open button-down shirt.

Wear combat boots with cropped fitted jeans for the perfect weekend outfit. Choose a pair of jeans that end 1 to 2 inches (2.5 to 5.1 cm) above the top of your boots to separate the pieces. Opt for a pair of heeled combat boots if you need a little extra height to balance out your silhouette. Balance out the combat boots’ edge with a more colorful, polished top, such as a black-and-white gingham button-down shirt beneath a yellow sweater. You could also continue the edgy theme with a black distressed long-sleeve shirt and a leather moto jacket.

Pair UGGs with medium wash skinny jeans for a warm, comfy look. The close-fitting denim will balance out the thicker, wider footwear and maintain your silhouette. Choose from an array of styles and colors, such as camel, black, cinnamon, blush pink, or gray. For a preppy look, choose a pair of mid-calf, cinnamon-colored UGGs, then add a cream sweater and a patterned blanket scarf. If you’re not sure about UGGs, you can always make the look more subtle and seamless by choosing a pair of black UGGs and black distressed skinny jeans. Add a white henley and a gray longline coat to make the look a little more polished, but still comfortable.

Scrunch slim-fit jeans over a pair of dress boots for a hipster touch. “Stack” or scrunch your slim-fit jeans above a pair of ankle or mid-calf boots for a look that's effortless without being sloppy. To scrunch your jeans, pull the hems up and let them naturally rest around the top of the boot. You can also tuck part of the hem into the boot to keep them scrunched up. Stiffer, 100-percent cotton blends will best be able to hold a scrunch. You could wear a pair of black dress boots with black slim-fit jeans, a tan T-shirt, and a distressed denim jacket for a more casual look. You could also dress up the look with some dark brown dress boots, medium wash slim-fit jeans, a brown knit long-sleeved shirt, and a camel longline coat.

Creating Outfits with Tall Boots

Wear skinny jeans with tall boots to avoid bunching. Rather than straight leg or wide leg styles that bunch up around the ankle, skinny jeans will easily tuck into boots. To keep your skinny jeans in place all day, tuck the cuffs of the jeans into the tops of your socks. This is especially important when your boots are fitted as well.

Pair thigh-high boots with super skinny jeans for a seamless effect. Thigh high heeled boots are an easy way to create a long, glamorous silhouette. Because the fitted skinny jeans and fitted boots transition seamlessly, they make your legs look longer and leaner. This look is perfect for a date or girls’ night. For example, you could wear a pair of medium-wash skinny jeans and some gray suede thigh-high boots with a lightweight black turtleneck.

Choose a pair of riding boots to give skinny jeans a classic, preppy look. The equestrian influence of the boots will elevate a pair of jeans, creating a timeless, sophisticated outfit. Go for some boots in a classic color, such as tan, black, or brown. Wear clean, non-distressed jeans with your riding boots to keep the look polished. For example, you could wear a burgundy silk top, a black blazer, a pair of dark-wash skinny jeans, and some brown leather riding boots for a classy, autumnal outfit.