Shopping for Shorts over 40

shopping for shorts over 40

Shopping for Shorts over 40


This is a guest post by Shannon Hale of Skip to My Life

“I love shopping for shorts!”  said no one, ever. Shorts shopping signals the beginning of summer for most of us. But for me, this single article of clothing symbolizes so much more.  Topped only by preparing taxes and dental work, searching for a passible option to bare my pasty legs is one of my most dreaded tasks.

Perhaps you can relate.  As moms of teens, we have a front-row seat to our youth-centered culture.  As we start to notice normal physical changes become more pronounced with age, we can quickly turn those changes into mental limitations if we’re not careful.  

Read on for tips about Shopping for shorts over 40.

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Shopping for Shorts over 40



I’d like to help you out a little, not just by simplifying your wardrobe, but also by giving you a positive message to take into the dressing room this season.  The first step is becoming aware of how we view our bodies and the limiting thoughts we’ve accepted as “normal”.

Here are a few that plagued me as I tried on shorts last week:

“How could you let yourself get this heavy?”

“At least you’re not as big as: (insert name of reality show star).”

“You’re getting older, of course you’re out of shape.”

In the span of about a minute, I completed a mental circle from shame to superiority to resignation and started over at shame.  I said things to myself that I’d be horrified to hear coming from the mouths of my kids or just about anyone I know. Like my old cut-offs, I realized my seriously outdated self-talk needed to be put out with the trash.  

Maybe you’ve experience similar negative body image thoughts and letting them limit what you wear, where you go, or new experiences you try.  If so, here are a few tips I found that updated both my look and my mindset.

I decided to start on my quest for awesome shorts by thinking about which styles make me feel put together and celebrate the shape I am today.  I narrowed them down to just three categories: the Jean Short, the Bermuda, and the Athletic short.

Each of these types serves a different purpose and is versatile enough to work in various settings.  I visited three retail stores available in most markets: Old Navy, JC Penney, and Wal-Mart. Here’s what I learned, along with pointers to help in your shorts-shopping adventures.


Most of us will experience a combination of these changes in our lower half as we voyage past 40.  


  • “Spider” veins or more pronounced varicosities
  • Stubborn abdominal or hip weight
  • Cellulite or uneven skin, especially in the upper legs
  • Stretch marks
  • Crepey or thinning skin
  • Sun spots


The smartest retail outlets have realized we will cross a desert to find a flattering pair of shorts that minimize the above characteristics.  Look for a store that’s abandoned the “one size fits all” mindset of yesterday and enjoy trying on clothing with your unique body type in mind.  



My must-haves in this category were:

Casual without being sloppy, and

Fitted, but not uncomfortable.  

A darker jean shrinks the mid-section visually so I opted to skip the light-washed looks.  





These shorts met all my requirements and then some.  They ran true to size and had a mid-waist that offered some support without looking like mom jeans.  I’m average height and prefer a longer inseam, but you could easily adjust these by rolling up the cuff.

Best of all, they offered a fun distressed detail without trying too hard.


JC Penney


Lee brand “flex motion” jean shorts offered a nice fit, were comfortable, and ran true to size, but were a bit too short for my taste.  They came with a scarf-type belt that I probably would never wear. Not a winner for me, especially at this price.


Old Navy


These ran a close second to the Wal-Mart brand for comfort, length and style.  They came in only one jean color, called Toise, which looks like a moderate wash and run true to size.  They are snugger fitting at the leg and won’t flatter every shape. Nothing put them over the top for me, but they’re a good option for the price.



This category of shorts needs to go from casual errand days to date nights.  A wardrobe workhorse, a great Bermuda should come in a variety of colors and make me look great.  




Wal-Mart’s closest selection to my needs was a pull-on version of the Bermuda, which made me feel frumpy.  I opted for this casual, knee-length, black dress instead and loved the fit and feel so much I bought another in grey.  This dress is very roomy so I sized down.


Extremely versatile, this cutie can be classed up with a jacket and sandals or just slipped on with a pair of tennies.   Hidden pockets! Need I say more?


JC Penney



Penney’s St. John’s Bay brand had an 11” inseam and midrise waist that ran true to size.  These felt great with just the right amount of support. They come in several colors, including a jean option.  


Old Navy


Seriously?  Old Navy really dropped the ball in this category.  Although they offered a variety of colors and cute prints, their version of the Women’s Bermuda was far too short for my needs.


I ended up on the guy’s side of the store with the Ultimate Slim men’s grey (Panther) Bermudas.  The fit was too baggy for my figure, and my son identified them as “guy’s pants” the minute I put them on.



Perhaps the trickiest category, the athletic short needs to allow for lots of movement while making me look great enough to want to slip them on and go for a walk.


I decided to venture out from the traditional short in this category and offer a variety of options.  Here’s what I found.




After trying on some real train wrecks in this category, I found a gem that made my trip to the Wal-Mart dressing room worthwhile.


This black, athletic Capri by Avia fell a few inches below the knee, offered a tummy-hugging high waist and was light and breathable enough for summer temperatures.  In black, it offered a classic look that could also be worn under a summer dress.


JC Penney


I have always admired the look of skorts on others, but it’s one of those “fantasy” wardrobe items that never seem to look like I hope it will once I try it on.  This black, athletic skort was a nice surprise!


It fell to just the right length, was very comfortable and ran true to size.  Unfortunately, I needed a bit more support in the tummy area to make it a winner for this price.


Old Navy



Old Navy redeemed themselves from the Bermuda debacle with these black, athletic shorts.  I feared they would be too short, but found them very comfortable and even needed to size down.  They offer great tummy support and silky feel with a fun side detail.


These are a great buy, especially if you can catch them on sale.


This weekend, I plan to go through my closet and pair down my shorts.  But I’ve also decided to replace some of my limiting thoughts with those below.


“You’ve set some healthy goals for the summer.  Good for you!”

“Give yourself time to get there.”

“Your body has served you well, be kind to it.”


I hope that, when my kids leave our home, they carry a positive view of their bodies resilient enough to withstand the blows of an unhealthy culture.  That goal, I now realize, starts with the way I speak to myself.


As temperatures rise and we bare a little more skin, let’s choose kind self-talk.  Instead of bemoaning shorts that no longer fit, why don’t we use that energy to embrace all our incredible bodies have done to get us where we are today.


I’ll be taking a KonMari sized clothes donation to the local resale store this weekend and wishing their new owner all my best.  In return, I’m looking forward to refilling my closet, and my mind, with my exclusive brand of self-love.


For pictures of Shannon in her winning shorts check out her post: Do you make these short shopping mistakes?


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Shannon Hale has been blogging at Skip to My Life since January, 2019. She lives in the heartland with her husband of 25 years, 2 fur babies and 2 mostly-grown children. She found life at home most fulfilling, her career was spent in the healthcare industry.  She learned the value of research-based decision making when it came to using the best products and services available to better her life and health. She has now turned her attention to home, health, and style after 40. 

You can follow her on Facebook and Pinterest.

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