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

Photographed by: Andrew Yee, Styled By: Ali Pew

Sweater-and-skirt combos land at the top of the easiest (and chicest) uniform to wear for fall. The missing piece? Which boots to step into. We did all the work for you and matched each skirt length with a boot type. Cold-proof a mini skirt with thigh-high boots (it's sexy without too much skin exposure), or give a midi skirt a lift with heeled ankle boots. Complete your fall outfits with our guide to the best and most flattering skirt-and-boot pairings out there.

RELATED: 8 Reasons to Buy Suede Boots for Fall

Start Slideshow

1 of 5

Mini Skirt + Thigh-High Block-Heeled Boot

Courtesy

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.

Advertisement

2 of 5

Flowy Midi Skirt + Midi Heeled Boot

Courtesy

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.

3 of 5

Knee-Length Central-Slit Skirt + Chelsea Boot

Courtesy

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.

Advertisement

4 of 5

Straight Midi Skirt + Heeled Ankle Boot

Courtesy

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.

Replay gallery

Share the gallery

Up Next

Advertisement