Shorts season is upon us, and I'm officially starting to run out of fun, fresh ways to wear the classic summer staple. So I did as I always do when I find myself in a wardrobe rut: I scrolled through Instagram in search of cool styling tricks. There's a certain shorts-and-shoes combo I kept coming across, and let's just say it's a polarizing one I never considered sporting this season. (Leave it to the feed to get me to try one controversial trend after another.)
This time around, I'm trying my hand at wearing ankle boots with shorts. Yes, the shoes you love to wear with your skinnies and wide-leg pants in the fall and winter are now also a summer must. In fact, fashion girls have been wearing them with everything from denim cutoffs to Bermudas to wool trousers. Itching to try something new? Read on to see the polarizing shorts-and-shoes combo that had me utterly intrigued and has managed to get me out of my outfit rut. Thanks, Instagram!
You can't go wrong with high-waisted shorts and black ankle boots.
Leather shorts look so good when styled with a pair of cowboy boots. Talk about cowgirl chic, no?
You probably never thought about wearing your bike shorts with tall cowboy boots, rights? I definitely am now.
Dr. Martens and distressed Bermuda shorts look so cool.
Play up texture by mixing prints, like wearing cheetah bike shorts with snakeskin ankle boots.
White ankle boots will team nicely with all your shorts, especially those of the denim variety.
Ground lightweight shorts with chunkier black boots for a cool juxtaposition.
Next up, 10 Bermuda shorts outfits everyone will be wearing this summer.
-
If You're Tired of Predictable Fall Outfits, Try This Styling Trick InsteadBold and anything but basic.
-
Just a Reminder: *This* Is the Best Pant Style to Wear With Every Type of BootThey're model-off-duty approved.
-
It's Boho Chic on a Budget—29 Gorgeous Free People Sale Finds I'm Absolutely LovingUp to 70% off!
-
5 Street Style Trends From Milan Fashion Week That Will Be Everywhere This FallTake notes.
-
Yes, You Can Wear Your Lace-Trim Shorts This Fall, But Only If You Style Them Specifically Like ThisImmediately re-creating.
-
Fine, I Won’t Gatekeep—These 27 Abercrombie Finds Are Too Chic to Miss (and They're All On Sale)I can't decide which fall pick is my favorite.
-
Not Skinny, Not Wide-Leg—J.Lo Just Wore Ankle Boots With 2025's Most-Wanted Pant TrendCopy this fall outfit ASAP.
-
This Dated Denim Pairing Is Suddenly the Chicest Way to Wear Jeans for Fall 2025Easy and stylish.
