The Best Ways to Wear Shorts for Women Over 40

It’s almost summer and that means it is time for shorter skirts, bare shoulders, and other clothing that bares a bit more skin than we’ve been showing all winter. While we love some fun in the sun, and the associated uplift in our moods and general happiness, sometimes summer clothes seem so much more complicated than cold-weather gear. No (or less) layering, more fitted pieces, less fabric, and the need to make sure we’re summer-ready can be stressful! This includes how to wear shorts for women over 40.

Shorts For Women Over 40

Is there any other piece of clothing more fraught with peril than shorts, particularly after 40? Determining a flattering length, level of tightness, and the appropriate amount of stretchiness, and what to pair shorts with only gets more complicated as we age.

After all, no one wants to look like mutton dressed as lamb but we all want to be comfortable and stylish! Read on to see our favorite shorts options for women over 40 in summer 2023.


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Best Ways To Wear Shorts

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Skort The Issue

Want the best of both worlds? Try a skort, or a combination of skirt and shorts. This Columbia skort with adjustable drawstrings is ideal for more athletic pursuits (even if that is just chasing after your kids or pets!) We also like the Earth Skort from Girlfriend Collective for every day outfits. There are dressier skorts out there as well, like this turquois asymmetrical one from Lulus that could be a fun vacation or date night piece.

Add A Little Flare

Shorts that are not super fitted around the leg openings or thighs are often much more flattering than tight shorts or bike shorts, since they skim over the body and flow almost like a skirt. There is a reason these 4″ Stretch Chino shorts from J. Crew are a consistent top seller, since they would work on nearly any figure. We like the summer green or vivid begonia for a fun summery statement! 

Go For A Print

An eye-catching print can actually help distract the eye from the cut of shorts and draw attention away from anything you want to conceal. For instance, wouldn’t these leopard shorts from Amazon look great with a black top and some interesting jewelry and sandals? Plus they are only $25.99.

Drawstrings For Casual Looks

Adjustability matters, and for casual wear a pair of drawstring shorts can be perfect. Something like these Eileen Fisher organic linen shorts are ideal for a variety of sizes and shapes.

City Chic Shorts for Women Over 40

City shorts are shorts styled more like dressy pants and usually made of a more refined or upscale fabric than other types of shorts. For instance, these Hybrid & Company womens 7 inch shorts available via Amazon would be a great choice to dip your proverbial toe into shorts this summer, and they come in a bunch of colors so you can be safe with black or experiment with brights, or both.

Not Your Standard Cargo

Cargo shorts have gotten a bad rap over the years, and for good reason! But now they are back on trend. And there are light, feminine versions like these Cali Cargo Shorts that would look wonderful with a button down top or similar breezy blouse. 

One thing we don’t necessarily recommend is cut-off shorts, whether you buy them pre-made like that or cut off an old pair of jeans yourself. They are fine for yard work, walking the dog, hiking, or other messy tasks, but wearing a more elegant or pulled-together pair can be much more flattering on an over 40 figure.   

Do you wear shorts in warm weather? How about on vacation? Let us know in the comments or in our Growing Younger Facebook group! 

Shop The Best Summer Shorts

– Jacqueline Zenn

You may also like to read more of Jacqueline’s styling posts like So What Is The “Old Money Aesthetic” and Why Should You Care? and Our Favorite Fashion Prints For Spring 2023 (That Aren’t Florals).

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3 thoughts on “The Best Ways to Wear Shorts for Women Over 40”

  1. Here’s the thing. If we didn’t fear judgment, we’d wear whatever we feel like. I don’t see why we have to be concerned with our age when we wear shorts …or our size. Acceptance is the rule for me! Of course, there are those People of Walmart photos…another story entirely.

    • I could not agree more. We write these more so women feel confident in wearing whatever the heck thay want. There are no rules. Just tips to help with confidence. Personally I do not feel right in shorts. One summer a few years back I put a pair on that I had for years and I just didn’t feel right in them. Can’t explain why. But my guy is telling me those days are over and I listen to my gut. But my voice is different than yours and everyone else’s. We all just have to do what feels right for us. I could care less about what others think.


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