The 10 Best Shorts for Women Who Think They Can’t Wear Shorts

We've got a pair for every figure, style, and budget.


God bless women who continue to wear shorts with supreme confidence regardless of their age. You look great! As for the rest of us (because it can’t be only me), the thought of sporting a pair of shorts started to lose its appeal after the age of about 40. That’s when I slowly started filling my closet with flowy skirts and sundresses and shoving the shorts to the back of the drawer.

Sometimes, though, you really need to pull on something easy, cool, versatile and casual. In other words, you need a pair of shorts! Whether you’re riding a bike, sitting on the grass at a picnic, on a vacation, or roughhousing with grandchildren, shorts offer a level of comfort and practicality that dresses and skirts can’t touch.

With that in mind, we’ve rounded up seven pairs of shorts that are easy to wear at any age. Whether you want to dress up or dress down, spend a little or a lot, downplay your derriere or camouflage dimpled thighs, one of these will work for you. Keep scrolling to shop Woman’s World‘s picks for the best shorts for women over 50.

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J. Crew 5-Inch Stretch Chino Shorts

Best Classic Chino Shorts
chino shorts for women
J. Crew

Buy on J. Crew ($49.50)

Why we like them:

  • Available in 6 versatile shades
  • Added stretch for ease of movement
  • Made from organic cotton

When in doubt, go with a classic. These tailored chino shorts come in a variety of versatile colors, including khaki, navy, olive, and white. A hint of stretch in the soft cotton fabric makes them perfect for active days, and a slightly higher rise than previous J. Crew versions — they sit just above the hip — means you won’t be tugging at them or fussing with the fit. Pockets lend practicality, and the fact that they’re machine-washable make these shorts a perfect choice for everyday wear. And to make you feel even better about purchasing these, J. Crew supports the Better Cotton Initiative, which advocates for more sustainable, responsibly grown cotton.

Promising review: “I finally realized at 40+ years old, I was no longer comfortable in shorts … Thank you J. Crew for offering cute, stylish, quality, on-trend shorts in a variety of lengths. I am a size 2/4, pear shaped, with solid, muscular legs. Shorts were always a hunt for me. These shorts are comfortable, and big enough in the thigh area. I purchased a size 4. The fit is perfect. I feel that the material will stretch a little with wear, but I like my shorts a little roomy and [to] ride low on my hips.”

GAP High-Rise Khaki Shorts

Best Khaki Shorts
khaki shorts

Buy on Gap ($30, originally $39.95)

Why we like them:

  • Available in 6 versatile shades
  • Added stretch for ease of movement
  • Made from organic cotton

With a 5-inch inseam and a high rise, these stretch twill cotton shorts are comfortable, cool, and modest. Cuffed hems and a single front pocket give them a classic look, and pockets in the back offer a place to slip your phone when you’re out and about. You can machine wash these shorts, and choose from white, olive green, or the tan color pictured here. Grab them while they’re on sale!

Promising review: “These shorts are a great basic. Very soft and good length. Nice tan color that pairs with everything!”

Best Shorts for Pear-Shaped Figures

pink boden shorts for women over 50

Boden Berwick Shorts

Where to buy: $85, Boden

If you struggle to find a pair of pants or shorts that can comfortably accommodate your rear without gaping at the waist, you’ll love these stylish Boden shorts. They feature a self-tie belt that hugs your waist, while the soft tencel-blend fabric drapes over your bottom half. Crisp pleats add visual interest in the front, and faux back pockets won’t add any bulk. Available in bright pink, vibrant green, or navy, these will change how you think about shorts!

Best Denim Shorts

affordable denim shorts

Amazon Essentials Denim Bermuda Shorts

Where to buy: $18, Amazon

Shorts for women over 50 don’t have to be formal, and this denim pair is begging to be worn at a backyard barbecue or lounging by the pool. More than 200 rave reviews on Amazon show that great shorts don’t have to be expensive to be loved, either! “I normally hate the way I look in shorts but I love how I look in these,” writes one happy customer. Soft stretchy cotton and a high-rise waist make these comfortable for any type of figure, and at this price point, why not give them a try?

Best Affordable Shorts

casual walmart shorts

Hanes Cotton Shorts

Where to buy: From $6.96, Walmart

When we say “affordable,” we mean affordable. At under $10, these cotton shorts, featuring pockets and a drawstring waist, are some of the best-reviewed shorts Walmart offers. “Perfect fit, perfect length, love them!” writes one buyer. “I plan to buy another five or six [pairs] because they’re so comfortable, and here in Texas it’s shorts weather year-round!” Snap up a pair in all four muted, go-with-anything colors, and you’ll have something easy to pull on every morning!

Best Dressy Shorts

pink flowy shorts for women over 50
Saks Fifth Avenue

Remain Birger Christensen Linen Bermuda Shorts

Where to buy: $180, Saks Fifth Avenue

Paired with a silk blouse, a belt, and some delicate jewelry, these flowy linen shorts are fancy enough for a night out on the town. Or throw a summer cardigan on top, and they work well for a day at the office. The pale pink color coordinates easily with a range of hues, and the breathable fabric keeps you cool. Fully lined and equipped with pockets, these dry-clean-only shorts will be your warm weather go-to for more formal occasions.

Best Casual Shorts

shorts for women over 50
Ann Taylor

The City Short

Where to buy: $49, Ann Taylor

Available in navy, black, and beige, these relaxed yet sleek shorts are made of a cotton blend with just a touch of spandex to give them a little stretch. Style them with a belt for a more put-together look, or go without for everyday, casual wear. These shorts are cut a little leaner through the hip and thigh and have a mid-rise waistline, for a flattering, classic line. And good news — they’re machine-washable!

Best Paperbag Waist Shorts

yellow shorts for women over 50

Brynn City Shorts

Where to buy: $98, Anthropologie

A paperbag waist lends these fun shorts a casual vibe, while a removable belt keeps them looking chic. They can be worn just as easily with a T-shirt as a button-down or camisole top, and come in a deep taupe shade as well as the pictured chartreuse. Side pockets make them practical, and a front-zip makes them easy to slip on or off over your favorite swimsuit at the beach. Note that these shorts are hand-wash only; keep them out of the washer and dryer so they maintain a perfect fit.

Best Shorts for Apple-Shaped Figures

bermuda shorts for women over 50

Vince Coin Pocket Bermuda Shorts

Where to buy: $78.75 (Originally $175), Nordstrom

Women with wider waists and slender legs, these Bermuda shorts are for you! These slim, tailored walking shorts are a shade of blue that goes with everything, feature plenty of pockets, and are machine-washable and dryer-safe as well. Made of a cotton-spandex blend, they have just enough stretch to be comfortable without losing their shape, and are long enough to be modest yet stylish.

Best Shorts That Aren’t Really Shorts

Anthropologie culotte shorts for women over 50

Mina Chambray Culottes

Where to buy: $98, Anthropologie

For the seriously shorts-averse, culottes are a fashionable warm weather alternative — and this pair from Anthropologie is versatile enough to become a staple of your wardrobe all summer long. Made of cotton chambray, they’re machine washer and dryer-friendly, have lovely pleated detailing in the front, and offer a super-comfy wide-legged silhouette. Dress them up or down to suit any occasion!

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