How to Wear It: Denim Shorts

Make Sure to Pick the Right Fit 

“To avoid looking like you’re trying to be 16 again, I would go with a more relaxed/boyfriend fit. It will be a little looser, and give you more length. Pairing them with a relaxed button-up blouse can give you a chic, effortless look. Throw on an ankle bootie or lace-up sandal to complete the look.”—Andrea Peña with Modern Society 

Pair Your Shorts Appropriately 

“Wear them with a sweater for transitional weather. Pair them with lace and silk to dress them up. Wear them with longer open kimonos, dusters and maxi dresses for a west coast vibe.”—Tara Hamilton with STAXX 

Don't Let Your Shorts Look Too Summery

“Avoid wearing crop tops with them. I would also avoid wearing flip-flops with them (unless you’re headed to the pool). I love the idea of cut-offs with an oversized sweater as we head into fall.”—A.P.  

Style Up Your Shorts For Work 

“I suggest going with a clean hemline versus a frayed edge. If you wear it with a dressier top, it will be more work appropriate. Also, keep in mind the length if you are wearing them to work and trying to maintain a professional feel. Add a silk cami and a blazer to add an office vibe. A lighter wedge, bootie, or heel can make the outfit seem dressier. I would suggest choosing a darker wash if you’re going for a more professional look. The darker wash can almost appear as more of a dressy short, rather than a denim.”—T.H. 

Pick Shoes That Work With Shorts

“Don’t wear them with stilettos or flip-flops. Do pair them with a pair of booties.”—A.P.

Mix Up Your Shorts Styles 

“Don’t be scared to play around with lengths and washes. You’d be surprised to see what works and how much a short can change an outfit.”—T.H. 

Become Comfortable Wearing Shorts

“You just have to find the right pair. Once you do, you’ll have them forever. I would start with a very basic, relaxed, mid-rise fit. Get out of the mindset that they are just for young girls who are wearing crop tops and going to music festivals. Get a second opinion if you aren’t sure. Whether that be from a sales associate, or husband, or close friend, it’s always nice to have that reassurance.”—A.P.

Ease Shorts Into Your Wardrobe

“Wear them for the first time with a group you’re comfortable with! It’s fun to branch out. Try it out with an easy baseball tee for a more relaxed weekend feel. It gets so hot in our summer months, and if you switch up your outfit with cutoffs, you’ll be much better off than being miserable.”—T.H. 

Don’t Be Afraid to Go Formal With Shorts

“Dress it up for a dinner date with something a bit more feminine to offset the casual vibe.”—T.H.