How to Wear Shorts When You're Over Age 30

If you've ever questioned if it's suitable to wear cutoff shorts after age 30, how short is too short, or what to wear with shorts in your 30s, this one's for you. We're well into the dog days of summer at this point, and if you've recently stepped outside wearing anything that covers your legs, you've probably noticed that shorts are a crucial wardrobe component (unless you like the feeling of your legs suffocating).

The celebrity set loves a good pair of shorts (especially the Los Angeles dwellers), so we turned our attention to those stylish women in their 30s who frequently wear them, to show us how to do it right. Surprisingly, our research proved that according to celebs, cutoffs (even quite short ones) are totally achievable for anyone, although some favor more tailored options. The secret to success lies in what you wear them with. In your 20s, it may have been NBD to just throw on an untucked T-shirt and go, but in your 30s, the key is to pair shorts with polished tops, jackets, belts, and shoes for a more sophisticated look. Want a visual example?

Keep scrolling to check out seven tips to shorts-wearing success in your 30s, and shop our favorite pairs at the end!


Wear tailored shorts with a tailored top.
(Image credit: Getty Images)

On Alessandra Ambrosio: Étoile Isabel Marant top and shorts; Jimmy Choo Lockett Snow Leopard Bag ($2350) and Harlow 80 Boots ($1195).


Try a matching set.
(Image credit: Getty Images)

On Ashley Madekwe: Atea Oceanie top and Bermuda shorts.


Put on a long jacket.
(Image credit: AKM-GSI)

On Chrissy Teigen: Janessa Leone Dahlia Wide Brim Hat ($264); Alexander Wang coat; Helmut Lang One-Shoulder Top ($125); R13 Double Layer Shorts ($205).


Wear special, elevated accessories.
(Image credit: AKM-GSI)

On Diane Kruger: Chanel handbag.


Tuck your blouse in and wear sleek sneakers.
(Image credit: AKM-GSI)

WHO: Alexa Chung


Top your shorts off with a kimono.
(Image credit: Splash News)

On Jessica Alba: Athena Procopiou kimono; Fidelity Denim shorts; Birkenstock Arizona White Birko-Flor Sandals ($100); Proenza Schouler PS1 Leather Pouch ($1325).


Wear a structured top and polished sandals
(Image credit: Splash News)

WHO: Jordana Brewster

Shop stylish shorts:

Allyson Payer
Senior Editor

Allyson is a senior editor for Who What Wear. She joined the company in 2014 as co-founder Katherine Power's executive assistant and over the years has written hundreds of stories for Who What Wear. Prior to her career in fashion, Allyson worked in the entertainment industry at companies such as Sony Pictures Television. Allyson is now based in Raleigh, North Carolina, and is originally from Baton Rouge, Louisiana. She holds a BFA in theater. Her path to fashion may not have been linear, but based on the number of fashion magazines she collected as a child and young adult, it was meant to be.