How to Wear Denim Shorts Over 40

Denim shorts go hand in hand with summer and never go out of style. While it does take trial and error to find the perfect pair, there are so many cuts, lengths, and washes; there’s a pair out there that will flatter you and your body type. My favorite pair of denim shorts are cutoffs. Something about them brings me back to summer days in the 80s and not having a care in the world. And while I’m not in my teens anymore, they’re still appropriate for any age. Read on for my tips on how to wear denim shorts over 40.

Just like jeans, denim shorts are not reserved just for casual wear. They’re versatile and can easily be dressed up or down, depending on the occasion. While I was looking back at my outfit of the day photos over the past week, I realized I had worn my denim shorts multiple times, creating a fresh look with each outfit.

What to Wear with Cut Off Shorts

Jean Shorts and Heels

A pair of low heels instantly dresses up a pair of denim shorts. I revamped the classic cutoff look by adding strappy wedges and a silky mixed-media tank top. My gladiator-style sandals not only add interest to this outfit but they lengthen your legs and bring the eye upward.

how to wear denim shorts over 40

Cutoffs / Tank/Similar/ Sandals

Denim Shorts with Long Sleeve Shirt

Whether you don’t want to show off your arms in the summer or want the added warmth when you’re in air conditioning, throwing on a long sleeve tee gives you that perfect balance. Another stylish option would be to roll up the sleeves of a button-up shirt and layer over your tank or short-sleeve top. I had fun with pattern mixing for this outfit, opting for a striped tee and animal print sneakers. The Panama hat completed the laid-back vibe for this look.

denim cutoffs over 40

Cutoffs / Tee/Similar/ Panama Hat /Sneakers (similar)

Wedges and Denim Shorts

As noted with the first outfit above, you don’t always have to wear shorts with sneakers or flats. Wedges, in my book, are probably the most comfortable type of heel because they’re supportive and easy to walk in. Opt for a nude or lighter color to make your legs appear longer. For this look, I dressed up my cutoffs with a floral peplum top, neutral wedges, and a statement necklace for a chic date night look.

denim cutoffs over 40