Style Inspo For Wearing Shorts From Celebs Over 40

The only thing harder than picking the perfect pair of shorts amid the various lengths, styles, and shapes on offer (plus the latest shorts trends) is deciding what to wear them with. Creating an outfit that's not only stylish and practical, but will also keep you feeling confident while flashing some leg, can feel impossible. But that's where fashionable celebs over 40 come in.

The likes of Carrie Underwood, Kate Middleton, and Kerry Washington have years of experience with the leg baring garments — and they've put it to good use. These stars 40 and over have served up some seriously chic outfits that will serve as your ultimate shorts inspo no matter what the season, occasion, or your style. So there's never been a better time to get leggy.

In 2016, Reese Witherspoon served the ultimate comfy yet stylish shorts ensemble while out in L.A. via her simple, baggy white T-shirt with bright pink, relaxed shorts. The outfit gave the actor room to move (this look is ideal for a sunny vacation, running errands, or any hot day when comfort is paramount), and the colors were classic, yet fun. She expertly accessorized the number too. Her nude, chunky heels were practical but polished and matched her sunhat and structured bag, which created a polished juxtaposition against her slouchy clothing.

Kate Middleton is the ultimate style inspo for wearing shorts over 40 if you want a casual yet polished look. In 2022, she tucked a navy-and-white striped sweater into white shorts, which she paired with white sneakers. Tucking in the top highlighted her waist for a flattering silhouette and created a more conservative look that won't accidently flash her torso. Middleton's versatile ensemble could be worn for formal and informal occasions, and is one of the many ways to bring tailored shorts into your wardrobe.

Jennifer Lopez gave a masterclass in pairing shorts with hosiery in New York in 2024. Lopez's look consisted of short leather-look shorts over black tights, which is ideal for women who want the style of shorts without the skin exposure. The shortness of the shorts and sheerness of the hosiery made the look sultry and spicy — not frumpy. She also showed how to make shorts work in winter by adding an oversized fur-look coat and hoodie that dialed up the glam but balanced out the skimpy, skin-tight bottoms.

Kerry Washington demonstrated how to put a breezy twist on formal shorts at the 2024 US Open. She tucked an open, navy, collared silk shirt (with a skin-tight vest underneath) into her ultra-high waisted cream shorts, but kept the shirt buttons undone to stop the 'fit being stuffy. The bottoms were neutral and perfectly tailored, and the brown waist belt that matched her heels and bag accentuated her figure. Washington's stilettos could easily be swapped to a flat brown shoe or sandal for those who prefer more comfortable footwear.

Carrie Underwood truly loves an outfit that shows off her killer legs and she displayed how to make shorts formal at the 2023 CMT Awards. Her look was part of an embellished silver co-ord. Matching her sparkly bottoms to her top ensured the 'fit was appropriate for a more formal event. She also paired the look with silver stilettos, as heels are notorious for elongating the leg and making the muscles look more toned. It's an ideal combo for those over — or under — 40 who want to really show off their gams.

Mindy Kaling made a case for denim Bermuda shorts. "The Office" star posed on Instagram in 2024 in the high-waisted, high coverage, bottoms with a black pinstripe blazer over a black bra. The longline blazer and shorts had a more conservative vibe, yet Kaling ditching a top added a spicy twist. The blazer also featured white lace that matched the lace on her shorts for a more cohesive aesthetic. Instead of heels, she wore comfortable black shoes with white socks, which made the look more practical.

In a 2022 Instagram post, Rebel Wilson made her beach shorts 'fit stylish by adopting the sandwich styling method. That involves wearing the same color in two garments, but separated by a second color. The "Bridesmaids" actor wore a sheer, black coverup and shorts, but made a statement via her hot pink swimsuit. Black may be unexpected for the beach, but it balanced out her eye-catching swimming costume color to stop the 'fit being too overwhelming. She also kept the garments flowy and breezy to balance out the structure of her formfitting swimwear.