How Kendall Jenner & Supermodels Made Very Tiny Denim Shorts With Booties the Big Summer Trend

Denim cutoffs are the go-to summer short, but paired with a T-shirt and flip-flops, the look can start to feel tired as the summer drags on. Celebrities have figured out the perfect footwear to elevate denim shorts this summer: boots.

There’s no one boot style that works with the classic short, but workboots might be the most popular item to pair them with. This calls to mind ’90s grunge — a look that’s back in style these days.

kendall jenner, fashion for relief, sergio rossi, cannes fim festival
Kendall Jenner wears Sergio Rossi pumps on the red carpet before the Fashion for Relief fashion show in Cannes, France on May 21.
CREDIT: REX Shutterstock

Model Stella Maxwell rocked her jean shorts with a matching jacket, topping off her look with black military-inspired boots. Model Hailey Baldwin also did the double-denim look in her chunky boots. The 20-year-old pulled off very short denim shorts and boots in style during Coachella, glamming up the look with statement earrings and bedazzled fishnets.

Hailey Baldwin, denim, boots
Hailey Baldwin wears a distressed denim jacket with her jean shorts for a double denim look, finishing her outfit off with sturdy black boots.
CREDIT: REX/Shutterstock

Other celebrities have gone in a different direction with their jean short and bootie pairings. Former Miss USA Olivia Culpo wore a pair of denim Chloé booties with her shorts, putting her own spin on double denim.

Olivia Culpo, denim, Chloé
Olivia Culpo wears cutoff denim shorts with denim Chloé booties in April.
CREDIT: REX/Shutterstock

Lucy Hale showed that denim shorts aren’t just a summer item. She stepped out in a long-sleeved white shirt with distressed-0denim shorts and Isabel Marant embroidered booties — a look that could work well into the fall even for someone who doesn’t live in a warm climate.

Lucy Hale out and about in Studio City, CA.
Lucy Hale out and about in Studio City, CA.
CREDIT: Splash News

Of course, the humble jean short can be elevated even further: Kendall Jenner wore a pair of cutoffs on the red carpet at Cannes, dressing them up with Gianvito Rossi pumps.

To see more photos of celebrities in denim cutoffs with boots, click through the gallery.

More From Our Brands

Access exclusive content