How To Wear Shorts In Your 40s and 50s And Still Feel Polished

We are often asked by our middle aged clients if they can still pull off shorts in an elevated way. And the answer is of course yes! Because we do understand that it can sometimes feel tricky styling shorts in your 40s and 50s… We wanted to pull a few looks together to give you an idea of how to effectively do this. Today, our stylists are talking in detail about how to wear shorts in your 40s and 50s and still feel polished.
Katie
This outfit strikes the perfect balance between casual and polished… Making it a great go-to for women in their 40s and 50s. The belted linen shorts offer a tailored yet breathable option for warmer days, with the structured fit adding a level of sophistication that feels age-appropriate without being stuffy. Linen is also a smart, timeless fabric choice—it drapes beautifully and keeps you cool without clinging. Layering a simple tank under an oversized white button-down provides light coverage and versatility. And the leather sandals, raffia tote, and gold accessories finish the look with effortless style. It’s proof that shorts can still feel chic, modern, and elevated at any age.

Silky Cotton Button-Up Shirt | Sunglasses | Scoopneck TankTop | Stretch Linen Short | Bangle Set | Slide Sandal | Straw Tote Bag
Katey
For a few years now I’ve preferred a skirt to shorts… But living in Tennessee, it’s impossible to pull off a shorts-free summer! I do love a flowy short either with a paperbag waist or drawstring like these. A tee shirt with a fun detail and a patterned short make your look feel elevated for lunch with friends or running errands around town.

V-Neck Tank | Large Gold Hoop Earring | Gold Paperclip Necklace | Printed Drawstring Short | Gold Strappy Sandal | Straw Crossbody Bag
Dana
A denim bermuda short is a great way to incorporate shorts into your wardrobe if you’re not typically a shorts gal. The longer length gives you a bit more coverage while still being stylish. Pair with anything from a tank to a sweater, heels to flats. Add some fun accessories and you have an easy, pulled together summer look.

Crochet Sweater | Sunglasses | Resin Bangle Set | Bermuda Jean Short | Ankle Wrap Block Heel Sandal | Canvas Tote Bag
We hope these ideas on how to wear shorts in your 40s and 50s and still feel polished were helpful! If you are middle aged, pull those shorts out, dress them up, and feel confident doing it!