The most important thing to keep in mind when pairing a dress with ankle boots is the length of the skirt. The best dresses to wear with ankle boots are those with hems that fall at the mid-thigh. Knee-length skirts or dresses are resounding “don’ts” with ankle boots because this skirt length makes your legs look much shorter than they actually are unless you wear opaque tights that match your boots. The style of the skirt does not matter as much as its length — you can wear dresses with pencil, A-line or flared skirt with ankle boots.
Ankle Boot Height
The height of the ankle boot’s heel as well as the shaft height also determine what length dress you should wear. In general, the higher your boot, the shorter your skirt should be. Pair ankle boots that rise a couple inches above the ankle with mini-skirts or short dresses. If you’re worried about your legs getting cold, wear opaque, patterned or textured tights to add more pizazz to your look — just make sure your tights or leggings complement the boot style and dress. Adding tights or leggings allows you to wear those mini dresses all year long. If you want your legs to look even longer, choose a stiletto heel instead of a flat. Wearing stiletto, wedge or platform ankle boots with short skirts gives you the maximum long leg look, but you can also get away with a skirt that falls mid-thigh to a couple inches above the knee. Flat boots can be worn with skirts mid-thigh or higher, but avoid skirts that have hems that fall lower than mid-thigh because you run the risk of looking shorter than you are.
What’s Your Style?
Accessorizing and picking the right boot style for your personal look is important. If you go for a ’90s punk rock-inspired look, pair a studded ankle boot with a leather-trimmed dress, and don’t forget to stack on some bangle bracelets and chain necklaces. The best dress choices for a suede wedge ankle boot might include a boho chic, flowy dress in a flowery soft cotton or solid jersey. Play with a mixture of hard and soft vibes by selecting a feminine dress and ankle boots with shiny patent leather accents, metallic details or belts and buckles. Let brightly colored ankle boots shine by pairing them with a black or neutral dress. Regardless of the style of your dress, from casual to cocktail, you can wear ankle boots.
Prints vs. Solids
Printed dresses look great with neutral ankle boots, especially when you add a solid-colored tight and a neutral jacket that matches or complements colors in the dress. Opt for a solid dress when your ankle boots have embellishments or a print of their own, such as leopard. These details of the ankle boots were made to shine, so don’t let your dress overpower the shoe. The best dresses to wear with ankle boots allow either your clothes or your shoes to be the star of the show rather than competing with each other.