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We’ve all stood in front of our mirrors in a new outfit asking, “Does this really work?” Case in point: wearing boots with skirts or dresses. A boot is a seemingly easy combination, but depending on the skirt and the boot, it can prove a bit tricky.

Pairing boots with a skirt is trying to balance a masculine item (boots) with a feminine one (skirt). It requires blending polar opposite styles in a way that makes it look like you aren’t wearing two outfits at once—and keeping your body proportions looking proper. Pair a too-long skirt with a too-tall boot, and you could instantly truncate your legs and end up with an out-of-proportion, unflattering look.

To master the boots-plus-skirt combo, here are a few key rules about length and style to keep in mind.

Booties //


Who doesn’t own a pair of chic ankle booties? Cute, comfortable, and versatile, this style can really earn its keep. Skinny jeans and booties? Always a win. But throw a skirt in the mix, and things get a little hairy. The best complement to booties is a midi skirt or something that hits you just above the knees. Keep it sleek for the office with a pencil skirt silhouette, or be flirty and feminine with an A-line.

The pencil skirt will highlight the feminine curves of your legs from thighs to knees, making the masculine short boots look more ladylike by emphasizing your shape. A flared skirt that hits at the top of your calves is also flattering because it will highlight the line between your ankles and calves.

Over-the-Knee Boots //


For those uber-fashionable over-the-knee boots, wear skirts that leave just a sliver of space between the tops of your boots and the hem of your skirt. You don’t want the tops of your boots to hide under your skirt hem. A little leg avoids a lumpy silhouette and an over-styled look. Try wearing these boots with a pair of colored opaque tights to break up your look while also keeping you covered during the cold months.

Classic Knee Boots //

For those wardrobe staple boots, like your equestrian-style riding boots that hit you right below the knees, opt for A-line skirts that hit at the knees or a couple inches above. Similar to the tall boots, the goal here is to not have the tops of your boots and the bottom of your skirt connect. Medium-height boots really highlight the outline of your legs, the tops of your calves, and the curves of your knees. Wearing a skirt that hits at your knees or just above will also highlight and flatter this curve of your legs. Plus, the fun, feminine A-line skirt will soften the masculinity of the boots. A pair of cable-knit tights or bunched boot socks will also add a stylishly cozy flair.