This Trending Skirt-And-Boot Outfit Combo Is One Of The Hottest Looks For Fall 2026

By Kelsey Goldbach
A woman wearing a black leather jacket, midi skirt, and boots. Edward Berthelot/Getty

We're going back to the '90s this fall: one of the biggest skirt trends of autumn 2026 is the timeless skirt-and-boot outfit combination. Throughout the 1990s, women paired skirts of all lengths (from mini to maxi) with knee-high or over-the-knee boots. Now, we're taking notes from them and pairing our favorite midi skirts with a variety of chic footwear options. Longer hemlines are among the transitional fashion trends to take you from summer to fall 2026, making the humble midi skirt our pick for the early fall. Ankle boots are one of the formerly buzzy fall style trends that are firmly outdated in fall 2026, so we're shifting our attention to higher boots — which just so happen to pair beautifully with a knee-grazing midi skirt.

There are plenty of ways to style this season's skirt-and-boot craze. Whether you prefer a practical shoe made of sturdy leather, rubber rain-resistant boots, or flashier footwear covered in animal print or suede, we know just how to incorporate them into your look. The best part about the skirt-and-boot look? It is incredibly versatile. Depending on the material of the skirt and boots, respectively, you can wear the outfit combination for dressier occasions or errand runs throughout the fall. This season, consider engaging in one of the hottest (and most timeless) trends.

Rubber rain boots a la Princess Diana contrast beautifully with a midi skirt

A woman wearing black rain boots and a white midi skirt. Jeremy Moeller/Getty

Rain boots are both practical and stylish — the perfect shoe for a busy autumn day. If you want to dial up the off-duty model vibes for fall 2026, this outfit combination is for you. Classic rain boots from Hunter were favored by high-profile celebs like Princess Diana, and they're still on trend today. Pair the simple yet chic boots with an ultra-feminine lace skirt for the ultimate contrast. 

Experiment with animal print boots and a contrasting skirt

A woman wearing neon yellow snakeskin boots and a pale pink wrap skirt. Edward Berthelot/Getty

Animal prints are the new neutrals, and we're here for it. If you're the type of person to enjoy making a statement with your footwear, look no further than animal print boots. The midi skirt and boots outfit trend is incredibly versatile, as this variation of the look shows. Upscale boots like the Nine West Gerty Knee High Boots in faux snakeskin provide an extra dose of glamour to any fall ensemble. They pair particularly well with a chic asymmetrical skirt like the Noma Midi Skirt from L'Academie.

Suede boots are one of the season's hottest shoe trends and they look stunning with a midi skirt

A woman wearing black suede boots and a blue pencil skirt. Moritz Scholz/Getty

Is there anything more fall than a pair of suede boots? The seasonal shoe is beloved during the cooler months, and for good reason — they're incredibly versatile. You can wear them to get in on the boots-and-midi-skirt outfit combination; for an especially chic look, pair suede boots in a neutral color like black, brown, or gray with a colorful skirt. One well-reviewed option is the suede Shoe'N Tale Knee High Boots.

Slouchy boots and a flashy skirt are a chic combo

A woman wearing a sequin-covered skirt and slouchy boots Moritz Scholz/Getty

Slouchy boots are one of fall 2026's most popular footwear trends. They may seem a bit retro due to their bohemian vibe, but we already know that September 2026 is an edgy revival of '90s basics. Instead of the expected pairings of denim and wool, switch things up with some much-needed texture. Style your slouchy boots with a flashy midi skirt like Betsey Johnson's fringe-covered midnight rodeo skirt or the ASOS black sequin skirt. 

Go monochromatic with a leather skirt and leather boots

Kim Petras wears black leather boots and a matching skirt to the 2026 Billboard Women in Music Event. Monica Schipper/Getty

We have plenty of tips for putting together the perfect monochrome outfit, and the combination of a black leather midi skirt and matching above-the-knee boots is an easy way to assemble a chic ensemble. While monochromatic looks can run the risk of looking outdated, all-leather is modern and edgy (not to mention perfect for the cooler months). Picking a pair of simple, high-quality, and stylish black leather boots from brands like Eloquii and Staud will make the rest of your look come together quickly.

White leather boots and an A-line skirt dial up the preppy vibes

A woman wearing a black A-line skirt and white leather boots. Edward Berthelot/Getty

When you think of leather boots, white probably isn't one of the first colors to come to mind. However, these preppy boots are in style for fall 2026, and they can be more timeless than you may think. If you want to embrace a classic vibe for the autumnal months, pair chic white boots like the 22élevé crocodile-embossed leather knee-high boots with a streamlined A-line skirt, such as Donna Karan's brown midi sweater skirt.

How we chose our recommendations

A woman wearing black embellished boots and a blue midi skirt. Edward Berthelot/Getty

We recommended different, trendy midi skirts and boots based on a variety of factors: price point, size range, and customer reviews. In order to ensure that our picks are accessible to as many of our readers as possible, we included both high- and low-priced items in our recommendations (as well as pieces that had a wide range of sizes available). Additionally, we looked at customer reviews across the internet for each individual garment.