Categories: Fashion

How to Wear Cut Off Jean Shorts

Have you noticed how cut off jean shorts are everywhere this summer? It seems like the more tattered and worn, the better. Ironically, cut off jean shorts remind me of my dad because, in high school, I stole an old pair of his Levi’s and made them into cut-offs I wore with this old 70’s belt. I’m not saying it was the best look, but it totally fit the 90’s grunge style at the time.

I was a bit leery about the resurgence of cut offs, so I decided to figure out some looks that would help explain how to wear cut off jean shorts. I actually do think jean shorts can work in multiple settings if you just pick the right items to help elevate the short’s super casual feel.

Casual Friday

Shorts – Rag and Bone
Blazer – J. Crew
Top – H & M
Sandals – Aldo
Bag – Valentino

For casual Friday, you can pull off cut off jean shorts as long as you pair it with something dressy on top and dressier shoes. If you paired this with flats or sandals, it just wouldn’t look dressy enough for work. I like the idea of a crisp white blazer and a flouncy blouse underneath to really dress-up the cut offs. High heels and a printed bag help to pull the whole look together, while making it fancy enough to wear with cut-offs for a casual Friday look.

Night Out

Shorts – Rag and Bone
Top – Moschino
Mules – Proenza Schouler
Clutch – Kate Spade
Earrings – Iosselliani

For a night out look, I paired the cut-offs with a black knitted crop top that has embellishments around the neckline. These funky heels will draw attention to the lower legs while the cropped top will show off a teeny waist. Adding a clutch with a fun detail and edgy earrings really draws attention to everything but the casual jean shorts for a fun night out look.


Shorts – Rag and Bone
Top – Calvin Klein
Sandals – American Eagle
Purse – MR.
Sunglasses – Le Specs

Cut off jean shorts are perfect for the weekend, but that doesn’t mean you have to look sloppy. A fun printed tank top paired with cute flat sandals, a neutral bucket bag, and modern sunglasses gives you a comfortable but put-together weekend look.

Are you wearing cut off jean shorts this summer? How do you style cut-offs?

Stacey Freeman: I am a Style Maven, Mommy, Educator, and Traveler.