How to Wear Ankle Boots with Jeans

Cuffing Your Jeans

Roll the hem of your jeans up 2 times to create a thin cuff. Cuffs are one of the easiest, most popular ways to pair skinny jeans with ankle boots. Fold the hem once, and then fold it over again to create a double cuff. The cuff should bring the lower edge of each jean leg just above your natural ankle, revealing a thin strip of skin between the boot and the jeans. Try to make it so that the visible strip of skin is around 1 inch (2.5 cm) wide. A small glimpse of skin can help lengthen the visual leg line, but too much visible skin can create a large block that makes your leg look shorter.

Cuff the hem of a pair of tight skinny jeans 1 time for a bolder look. A single cuff can create a bold block at the bottom of the jean, without revealing too much skin. Fold the hem up one time to make a cuff that’s 1–2 inches (2.5–5.1 cm) wide. Single cuffs are great for people who have long legs. If you have shorter legs, try to keep the cuff smaller than 1 inch (2.5 cm) to avoid making your leg look short.

Fold the hem inside of the jeans for a hidden cuff. If you don't like the cuffed look, try folding the hems inward instead of outward. Tuck the hem inside of the leg of jeans until you create about 1 inch (2.5 cm) of space in between your jeans and your boots. It's best to fold the jeans only one time for a hidden cuff. To keep the fold in place throughout the day, you can iron the new hem at the bottom of the pant leg.

Avoid tucking the hem into the boot. While it might seem tempting to tuck your jeans into the boots, doing so can actually make your legs look shorter. When your jeans are tucked, they can bunch around your ankles, making them look wide and disheveled. This is even true for skinny jeans, which tend to be tighter than straight-leg or bootcut. Even though they might fit into the top of the boots, you should cuff them to prevent bunching.

Picking the Right Jeans

Opt for a pair of skinny or straight-leg jeans if you want to cuff them. Skinny and straight-leg jeans tend to be the most flattering style to pair with ankle boots. They hug your curves and stay cuffed for a long time when you fold them. Skinny jeans tend to be the best option since they’re stretchy and don’t show many bumps when folded or cuffed. However, straight-leg jeans can help to create a more relaxed look.

Pick a pair of bootcut jeans to wear them untucked. These jeans are fitted around the hips but flare out slightly below the knee, making them a great cut to wear with ankle boots. Instead of trying to tuck or cuff these jeans, allow them to fall directly over the top of each boot, covering the top portion. Try to stay away from cuts that have extremely flared hems. These tend to break up your leg and can make them look short.

Purchase a pair of cropped jeans to show off the tops of the boots. Look for a pair of cropped skinny or straight-leg jeans that leave around 1 inch (2.5 cm) of space in between the bottom of the jeans and the top of the ankle boots. This tiny strip of skin creates a professional and polished look, without the hassle of tucking or cuffing the jeans. If you have an older pair of skinny jeans, you can make your own cropped jeans by using a sharp pair of scissors to cut the jeans just above your ankle. Use a tape measure and pencil to mark off the section you'd like to remove.

Make sure the hem is at least 1–1.5 in (2.5–3.8 cm) off of the ground. Try on your jeans without the boots first. Ideally, the lower hem of each leg should hit at about midpoint of your ankle. If the hem is touching the ground, your jeans are too long. If your jeans are too long, they can bunch around your ankles, making your legs look shorter than they are.

Selecting the Best Boots

Pick a boot with a heel that is at least 2 in (5.1 cm). To elongate your legs and add a bit of height, pick a pair of ankle boots that are slightly taller than an average pair of shoes or flats. The heels can be chunky, stacked, or even stiletto, as long as they’re a reasonable height and you can walk in them. If it’s your first time wearing heeled boots, look for a pair that have a chunky heel that’s right around 2 inches (5.1 cm) tall. These will be comfortable for standing and allow you to walk naturally without tripping.

Look for a pair of boots that hit higher on the ankle for wearing with jeans. Some ankle boots hit low on the ankle, just below the ankle bone, and are meant to be worn with dresses and skirts. Find taller ankle boots that hit at the ankle bone since they’re best for pairing with jeans. If the boots hit lower on the ankle, they can make your legs look shorter because they reveal more skin.

Pair brown boots with light wash jeans for a relaxed look. Although you can wear almost any color of jeans with ankle boots, brown boots paired with light wash jeans are a classic and comfortable style. Try to stick with a medium-toned brown leather or suede boot, and a very light or acid wash jean for the best results. If you don’t want to wear leather or suede, there are many high quality imitations that can help you create this classic look.

Select a pair that matches the color of your jeans to elongate your legs. If you want to make your legs appear longer, match the color of your boots to the wash of your denim to create a monochromatic look. You can also opt for a boot with a higher heel to make yourself look even taller. The easiest way to pull this off is by wearing a pair of black ankle boots with a pair of black denim skinny jeans. Both the jeans and the boots are a flattering color and style, and will help to make your legs look long and slim. For a smooth transition from the boots to the jeans, fold a hidden cuff in the jeans.