Best Ways to Show Off Your Over The Knee Boots with a Skirt

Let’s just get this out of the way: Yes, Pretty Woman featured Julia Roberts working the corners of Hollywood Boulevard in a pair over-the-knee boots with a skintight cut-out dress and, no, we don’t endorse trying the same ensemble beyond Halloween. But after logging several, infinitely more respectable years on the runway and street style scene, the thigh high design has clearly redeemed itself. Where pre-Rodeo Drive makeover Vivian gave you one bad way to wear it, fashion can offer up dozens of chic and sophisticated alternatives.

Our favorite option of the moment? Teaming super tall footwear with skirts of all lengths (even short ones—more on that below!) in lieu of tights, especially when the two pieces contrast in an interesting way. Think of a lace and embroidery-clad Cara Delevingne on her Suicide Squad tour, her famously long stems encased in black suede, or Selena Gomez in March of 2015, who updated the old school denim mini by swathing two thirds or her legs in stretchy black fabric. Now it’s your turn to get in on the action! Scroll down for 6 skirt and over-the-knee boot formulas that feel so right now.

1. H&M SKIRT & SCHUTZ BOOTS
Making this combo work for the office is all about the right balance of full coverage and conservative elements: menswearish fabric, blocky heels, bottoms that pass the fingertip test. Patent finishes and pointy toes need not apply.

2. TOPSHOP SKIRT & YEEZY SEASON 2 BOOTS
Don’t let the prim-and-proper shape and girlish color fool you! Teamed with a leggy silhouette and rugged shade of forest, a blush mini has plenty of swagger.

3. BALENCIAGA SKIRT & SAM EDELMAN BOOTS
Anchoring an abbreviated hemline with rough-and-tumble details—rounded toes, lug soles, and matte leather are all good things to look for—let it feel more streetwise than sultry. (Editor Tip: This under-$70 mini from Zara is a less expensive, but equally awesome, way to finish this look.)

4. ZARA SKIRT & KENNETH COLE BOOTS
As spring’s ’70s-inspired craze continues straight into fall, take advantage by combining thigh-skimming footwear in tan suede—for a splurgier option, Saint Laurent just came out with this fantastic pair—with a retro-chic pleated midi.

5. JACQUEMUS SKIRT & ZARA BOOTS
Repeat after us: the frillier the skirt, the sleeker the boot. And if the fit hits extra high on your leg, aim for an asymmetrical finish or side slit to show the additional length off. (This Vince Camuto design would be a great way to go.)

6. ISABEL MARANT SKIRT & STUART WEITZMAN BOOTS
A brilliant way to take this trend into the weekend: with snuggly sweater textures and flat, window shopping-friendly soles.