With a front-row seat—and often a backstage pass—to fashion's most in-demand runway shows, Kendall Jenner is one of the few members of fashion's inner circle I return to for styling inspiration season after season. Counting famed designers and celebrity stylists amongst her nearest and dearest, if the model isn't witnessing the creation of the freshest trends, she's setting them.
While Jenner takes a relatively laid-back and minimal approach to her daily looks, she's also partial to the occasional new-season trend, making her the perfect muse for easy outfit inspiration. Now, as we move further into the winter season I'm inspired to give my wardrobe a Jenner-approved refresh, and her recent outfits have convinced me that a chic, simple miniskirt is the perfect place to start. Styling pretty minis in a range of colours and cuts, I wanted to wrap my head around the specific shoe trends that Jenner always pairs with her favourite short skirts.
If you're also interested in exactly how Jenner makes a miniskirt look chic every single time, read on to discover the 5 shoe pairings she loves to wear with them.
1. MINISKIRT+ KNEE-HIGH BOOTS
Style Notes: Spotted out just this week wearing an all-black ensemble, Jenner styled her chic black mini with a tall pair of tonal knee-high boots. A classic combination that fashion people come back to across the coldest months, Jenner's two-piece look was simple enough to suit her laid-back style, but elevated enough to see her through her evening occasion.
SHOP MINISKIRTS AND KNEE-HIGH BOOTS:
This also comes in 10(!) other shades.
Style with a miniskirt or pair with a flowing dress.
In my opinion a simple black skirt is a wardrobe non-negotiable.
These also come in burgundy.
2. MINISKIRT + LOW-HEEL COURT SHOES
Style Notes: Sorry ballet flats, but this season fashion people are embracing the outfit-enhancing potential of a sleek court shoe. Adding the most sophisticated energy to their daily styling, the elegant shoe trend will elongate any outfit—making it the perfect pairing for a thigh-skimming skirt.
SHOP MINISKIRTS AND COURT SHOES:
Stye with the matching vest or wear this with a roomy knit.
These little heels are perfect for party season styling.
A classic piece you can wear during the summer months too.
These also come in a mesh style.
3. MINISKIRT + BROGUES
Style Notes: If you're looking for a shoe to make your favourite miniskirts feel more wearable for the day-to-day, then a polished lace-up style in the perfect place to start. With a flat shape and a smart finish, these smart shoes will make your minis feel so much more wearable.
SHOP MINISKIRTS + LACE-UP SHOES
This light beige shade is so easy to slip into a capsule wardrobe.
Style with a miniskirt or pair with tailored trousers.
Layer this with thick tights and knee boots for a cosy winter look.
These are well on their way to selling out.
4. MINISKIRT + SHEARLING-LINED BOOTS
Style Notes: As we move further into the coldest season, obtaining and retaining warmth becomes my number one priority, and my years of chilly winters have made me appreciate that there's no shoe more up to the job than a fur-lined boot. Copy Jenner's lead and style with a fuzzy skirt, otherwise pair with a wool mini and tights for a winter-ready silhouette—it's very Y2K and the most daring of her combos, but if you're willing to give it a try, so am I.
SHOP MINISKIRTS + SHEARLING-LINED BOOTS
Shop the miniskirt Kendall loves.
These cosy boots are ideal for mid-winter styling.
The chocolate brown colour trend is taking off this winter.
Shop these whilst they're on sale.
5. MINISKIRT + ANKLE BOOTS
Style Notes: Sometimes the simplest combinations really are the best, and a miniskirt and ankle boots outfit is one that I'll never tire of. To achieve streamlined a look style your shoes and skirt in a matching shade, and pair with tonal tights for a cohesive silhouette.
SHOP MINISKIRTS + ANKLE BOOTS
Style with the matching belt or wear this without.
Trust me—these won't stay in stock for long.
Style with a draped blouse or wear with a comfy knit.
These also come in three other shades.
-
Sabrina Carpenter Just Dressed Exactly How L.A. Girls Do When They Visit NYC During WinterCozy and colorful.
-
Stylish Women in NY and L.A. Always Wear Their Levi's With This Classic Shoe TrendFrom Lily-Rose Depp to Dakota Johnson.
-
Sydney Sweeney Just Wore the Winter Shoe Trend Rich Women in NYC and Paris LoveAnd just like that, a higher tax bracket.
-
25 Cute Winter Tops That Will Look Incredible With JeansFor your night-out rotation.
-
Who Needs a Stylist When This New AI Tool Just Dressed Me for Free?My new virtual BFF.
-
Buckle Up—This Sydney Sweeney–Approved Shoe Trend Will Be Everywhere in 2025I have proof.
-
Move Over, Black Tights—Everyone Is Opting for This Richer-Looking Color InsteadWe love a luxe-looking trend for under $20.
-
Bella Hadid Wore the Pant Trend L.A.'s Chicest Women Wear Instead of Skinny JeansMy other style muse just did too.
