Too often we pigeonhole our wardrobe pieces, prescribing them to certain looks or deeming them inappropriate for everyday wear, when both are far from being true. And so as we break into our boots, one of our favorite fall staples, we started looking for outfit inspo beyond cuffed jeans and printed leggings, which lead us to skirts. Though there are a few more rules to keep in mind to ensure your legs look long and lean with this ladylike combo (no one likes looking like they’ve been cut off mid-calf), once you ace those basics on your bod, the look is all the more put together. As far as styling goes? That’s where we’re coming in with 18 street style-approved ways to boot up in a skirt this fall.
Trendy Booties + Office-Ready Midi
1. Full Midi + Biker Booties: Pairing ultra-girly girl pieces like this full midi skirt ($42) with edgy biker booties ($88) is an easy way to strike a style balance that isn’t too pretty or too punky. Toss on a more casual cropped sweatshirt to make the look just right.
2. Ribbed Bodycon Midi + Gold-Heeled Booties: A ribbed, bodycon midi is one of the sexiest ways you can stay warm this fall. Flash some ankle in these cutout booties ($57) with gold details that pop against this smokin’ olive skirt ($29). Keep the silhouette on trend with cozy-as-ever oversized knit.
3. Pencil Skirt + Plunge Booties: Wipe the image of black pencil skirts from your mind forever. Make a bolder statement in a brightly colored version ($16) that’s boardroom-to-bar ready with a pair of plunging booties ($80).
Go-To Ankle Boots + Everyday Skirts
4. A-Line Mini + Wooden-Heeled Ankle Boots: Start thinking of your favorite flirty skirt as a throw-on-and-go option on par with your street-worthy sweats, just way more refined. That’s even if you pair an A-line mini ($45) with your most casual gray ankle boots ($99). And be sure to pass up your canvas tote for one that strikes a dressy note.
5. Slitted Maxi + Combat Boots: Embrace the new neutrals of the season with this dreamy combination of a blush-hued maxi skirt, slit not optional, ($50) and sand-shaded combat boots ($170) — it’s the dusty colors that make this casual pairing chic.
6. Floral Skater Skirt + Lace Up Boots: Floral skater skirts and lace-up boots were a perfect pairing in the ’90s, and they still are today. Update this throwback classic with a breezy, chiffon flared skirt ($50) and preppy leather lace-ups ($89) that can still surprise in a light maroon hue.
Clunky Boots + Girly Skirts
7. Plaid Pencil Skirt + Big Buckle Boots: Give a plaid pencil skirt ($158) a whole new life when you swap out pumps for thick-soled booties ($300). The buckle details help give this once-posh wardrobe staple a grungy vibe that’s right on trend.
8. Pleated Skirt + Lace Up Flatform Boots: Opposites do attract, as you can see here in this perfect pairing of a flowy chiffon mini skirt ($30) and clunky platform lace-ups ($160). Take the look to the next level with knitted knee-highs and an embellished beanie.
9. Lacy Skirt + Platform Booties: If you ask us, there’s nothing more sartorially stunning than mixing lace and leather. A raw-hem skirt ($129) somehow looks even lovlier in contrast to clunky ankle boots ($73), which we adore equally.
Posh Tall Boots + Fashion-Forward Midi Skirts
10. Scuba Midi + Embellished Knee-Highs: Olivia Palermo’s scuba skirt + tall boot pairing was most definitely the inspiration that sparked this look, and it’s surprisingly easy to copy. Stick with a baby blue knee-length skirt ($40) and pair with a milk-chocolate-y set of embellished steppers ($149) that also hit right at the knee.
12. Lacy Midi + Leather Stiletto Knee-Highs: Here’s another way to hack the to-the-knee look so that you’re showing just the right amount of leg. Opt for a black lace midi ($25) that pairs perfectly with basic knits and stomp the streets in leather knee-high stiletto boots ($189).
Show-Stopping Thigh-Highs + Skirts With Flare
13. Peplum Mini + Riding-Style Boots: Mini skirts in the fall? It’s more than doable when you rock a colorful peplum mini ($124) with unmistakably fall pieces, like these over-the-knee riding-style boots ($50) and punchy patterned tights. Seems like the perfect cold weather date outfit, right?
14. Fit + Flare Skirt + Heeled Over-the-Knee Boots: This might be our favorite way to wear black and white this fall: pair a fit and flare skirt ($40) with over-the-knee stiletto boots ($31) for a fresh take on a fancy look.
15. Skater Skirt + Matching Over-the-Knee Boots: We love the idea of using your thigh-high boots as a makeshift matching set for a super stylish twist on a monochrome outfit. Look for boots in a color that’s a little less obvious than black or brown, like this faux blue suede number ($60), then pop on the frilly skirt ($19) — and top, and bag! — to match.
Leather Boots + Leather Skirts
16. Zipper Mini Leather Skirt + Leather Chelsea Boots: This is one of the easiest ways to incorporate a leather-on-leather look into your weekly rotation. A modern-cut leather mini skirt ($200) with eye-catching zip details will ensure it stands out among your everyday layers, and you’ll never ever want to slip out of these go-with-anything cropped ankle boot ($65).
17. Full Leather Midi + Dressy Ankle Boots: We’re obsessed with this girly take on a leather skirt — and you should be, too. This full leather midi ($375) is actually a breeze to style: button up a silky blouse, toss on a long cardigan, and don’t forget a set of pointy-toe leather boots ($140) to hold the look together.
18. Leather Pencil Skirt + Leather Pointed-Toe Booties: Style this newfound closet staple like a pro by pairing your leather pencil skirt ($50) with pointed, high-heel leather booties ($159) that streamline the already impossibly cool look.
What’s your go-to skirt and boot combo? Tell us about your favorite ways to wear and restyle fall staples in the comments below.