How To Wear Shorts When You’re Over 40

Shorts are some of the most complicated garments for a lot of us, especially as we get older. From concerns about cellulite, visible veins or varicose veins, or simply just not having what we perceive as being “model perfect” legs, shorts can seem fraught with fashion peril. But shorts can be a lot easier to style than you think. Here’s how to wear shorts if you’re over 40.

How To Wear Shorts Over 40

That said, shorts are some of the most comfortable and practical pieces for summer and hot weather in general. There are so many excellent options out there now, that you have practically no excuse for not giving at least one of them a try. Here’s how to wear shorts when you’re over 40 and some of our favorite styles.

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Halogen Soft Shorts, $59 | Theory Lynie Tailored Shorts, now $146.25

City Shorts

This more tailored style is one of the easiest ways to wear shorts. These Halogen shorts look both comfortable and stylish – a rare and valuable combination during the hottest days of the year. Theory does the city short look well, and this pair would be a great option. Some women can go shorter but an inseam of at least 5-6″ is a good length for most women over 40. We’re fans of pairing shorts like this with a drapey blouse or even a contrasting blazer (if you’re going to be in some serious air conditioning).


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How to wear Sailor shorts over 40 fountainof30
Derek Lam 10 Crosby Sailor Shorts, $325 | Express High Waisted Button Sailor Midi Short, now $19

Sailor Shorts

A buttoned-up nautical look is a perpetual summer classic. We’re fans of these impeccably tailored Derek Lam 10 Crosby sailor shorts as well as this cheap and chic version from Express. Wear them with a crisp poplin or linen button down for a traditional look, or a fitted tee for something with more edge.

Paper bag Waist Shorts fountainof30
Leith Buckle Belt Paper bag Waist Shorts, $55

Paper Bag Waist Shorts

You might remember this look from the nineties, but the new versions of paper bag waist shorts are definitely more flattering. The modern way to do a paper bag waist is with a fitted tank or tee and some wedges – it’ll elongate your legs and showcase your upper body. This belted style by Leith would be an excellent choice.

Tie Waist Shorts fountain of 30
J Crew Cotton Poplin Tie Waist Shorts, $69.50

Tie-Waist Shorts

If you want to show off your waist and dress up a standard summer shorts ensemble, these are your best option. Similar to a paper bag waist but with a built-in sash belt, these are the ideal way to show off a narrow waist and to draw attention up from your legs. These J.Crew poplin shorts would be great for a variety of situations and could be dressed up with a silky tank or blouse or dressed down with a cotton tee.

Bermuda Frayed Denim Shorts black
Frame Le Vintage Bermuda Frayed Denim Shorts, $195

Denim Bermudas

Carol already said it perfectly, and these Frame denim Bermudas are a great option if you want to do a trendy shorts look with a little more coverage.

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Current/Elliott Cotton and Linen-blend Twill Shorts, $198

Twill Shorts

The traditional summer style of twill or chinos type shorts has been updated with styles like this Current/Elliot pair. Wear them with a tucked-in button down for a cool and elegantly casual outfit. Olive tones might be the most versatile and current shades this season.

denim shorts how to wear over 40 fountain of 30
RE/DONE Frayed Denim Shorts, $195

Denim Shorts

If you’re going to do the laid-back denim look, then go a bit upscale with the construction and wash, like this gray-black pair from RE/DONE. Think similarly with your accessories. You might be wearing denim and a tee, but that doesn’t mean you can’t take the look up another level with some statement jewelry or sandals. Avoid anything too “destroyed” looking unless you want to look like you raided the junior’s department. The key to wearing denim shorts now is finding something that’s subtly distressed and fits perfectly.

You should also keep in mind that when you’re wearing shorts, your footwear takes center stage. Low-top sneakers or flat sandals tend to be best for casual looks, but wedges or embellished flats are great if you want to be a little dressier. A bit of self-tanner also never hurts if you want some extra confidence.

Do you wear shorts in the summer? Are they only for super casual days or working in the garden, or do you dress them up?

–Jacqueline Zenn

You may like to read more of Jacqueline’s styling tips like Sun Hats: How to Protect Your Skin And Still Look Stylish and What to Wear to A Wedding This Summer.

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