I Tried 7 Shoe Styles With Denim Shorts and These Won

A wardrobe basic, a summer staple, and tricky to wear: Denim shorts are all these things. Sure, denim is undeniably versatile, but shorts show a lot of leg, making the shoes that we wear with them somewhat of a head-scratcher. So I decided to put seven shoe styles that are commonly worn with denim shorts to the test.

I started with my newest pair of "jorts", which feature a mid-length inseam and a vintage feel thanks to the 100% cotton construction. With a 3.5-inch inseam, the cutoffs are longer than many shorts on the market, but they're still quite short, all things considered. While I stood away from super-high heels, a multitude of other styles in my closet was fair game, from two different types of sneakers to espadrilles. When it comes to the most flattering shoe style to complement the shorts, there was a clear winner in my mind. All that said, it's worth noting that the styles that didn't work as well for me could look amazing on you. Shorts style and length certainly plays a role, as does height (I'm 5'4", for the record).

Read on to see my ranking and shop the shoe styles, along with some of my favorite denim shorts on the market.

#7: Flat Sandals

I was a bit surprised to see just how unflattering the flat sandals looked with my shorts, especially since that's the shoe style I wear most often with them. This was the flattest shoe style I tested, so I'm thinking that's the culprit.

Shop the Shoes

#6: Ankle Boots

As I expected they would, the ankle boots cut my legs off, making them appear shorter. That said, the small block heel of these boots made them a little more flattering.

Shop the Shoes

#5: Athletic Sneakers

The soccer mom vibes were definitely stronger than I prefer with this combination, and the sneakers felt a little too clunky with shorts, but I love them with leggings.

Shop the Shoes

#4: Espadrilles

While I liked the South-of-France vibes that the espadrilles provided, I found that the ankle strap cut off my legs in a less than flattering way.

Shop the Shoes

#3: Loafers

I love the polished yet effortless look that loafers bring to denim shorts. Case in point.

Shop the Shoes

#2: Kitten Heels

I was surprised by how much I liked this combination, as heels are oftentimes a no-go with shorts, but the heel was high enough to be elongating and low enough to be tasteful.

Shop the Shoes

#1: Slip-On Sneakers

Slip-on sneakers were the winners in my book. These added a little height and balanced out the abbreviated hemline of the shorts while looking effortless, as everything in summer should.

Shop the Shoes

Shop Denim Shorts

Next, shop the five brands with the best plus-size denim shorts.