The Most Flattering Skirt-and-Boot Pairings to Wear for Fall

Balance your mini with a thigh-high boot for a killer mod vibe. A block heel (versus a stiletto) will help tone down the sexiness of the boot. Treat them as an alternative to your favorite leather leggings.

Shop the combos (clockwise from top left): Opening Ceremony boots, $870; farfetch.com. Acne Studios skirt $490; net-a-porter.com. Stuart Weitzman boots, $655; stuartweitzman.com. Isabel Marant Etoile skirt, $240; matchesfashion.com. Sam Edelman boots, $250; samedelman.com. Tibi skirt $325; tibi.com.

A midi boot that hits right below your calf is a must-have this season, but the style is, admittedly, tricky to pull off. Find a pair that's roomy at the opening (as opposed to one that clings to your skin) and team it with a flowy midi to reveal just a sliver of skin.

Shop the combos (clockwise from top left): Alice + Olivia skirt, $722; mytheresa.com. Atelji 71 boots, $395; shop.com. Topshop skirt, $105; topshop.com. Carvela boots $269; asos.com. J. Crew skirt, $128; jcrew.com, Gianvito Rossi boots, $1,160; net-a-porter.com.

Offset a feminine pencil skirt that boasts a sexy central slit with a masculine Chelsea boot.

Shop the combos (from left): Proenza Schouler skirt, $858; farfetch.com. Dr. Martens boots, $140; drmartens.com. Mango skirt, $60; mango.com. Tod's boots, $645; saksfifthavenue.com. Carven skirt, $460; intermixonline.com. Balenciaga boots, $845; net-a-porter.com.

A midi skirt will keep your legs warm throughout the cooler months. It's optimal pairing? An ankle-grazing boot to counter the longer hemline. 

Shop the combos (from left): Zara skirt, $50; zara.com. Rag & Bone boots, $525; rag-bone.com. Theory skirt, $295; theory.com. Jeffrey Campbell boots, $180; nastygal.com. A.L.C. skirt, $510; matchesfashion.com. Coach boots, $375; coach.com.