
These top 3 winners for shorts over 40 will help you feel confident and look great this season! Stay in budget and on trend with these reviews.

Top 3 Winners for Shorts Over 40
In an effort to make the most of my budget, I limited my shorts categories to the 3 must-have groups: the Jean Short, the Bermuda, and the Athletic Short. I also limited my shopping to 3 retail locations: Wal-Mart, JC Penney, and Old Navy. Most of my winners are found in a variety of options, so even if I list them in only one category, there are often cross overs.
For more behind-the-scenes information on my journey to self-acceptance, check out my guest post on Almost Empty Nest.
The Jean Short
My requirements for jean shorts were:
- Casual, not sloppy
- Fitted, not stiff or uncomfortable
- Dark wash
- Updated detailing
- 11 inch inseam

At just $13.92, these were quite a bargain. They fit true to size, met all my requirements, and had an adjustable-length cuff. The distressed detail adds a little fun without trying to look too young. They also come in a lighter wash, if that’s your look.

At a higher price point of $44.00, my standards were pretty high. These shorts were fun and felt great, but just too short for my taste. They also came with a scarf-type belt I knew I’d never wear.

Priced at $24.99, these shorts were a nice pick, but nothing really special. Color is limited to one choice, a moderate wash. They’re a great option for Old Navy lovers or for those of you who have store bucks.
The Bermuda Short
My requirements for the Bermuda:
- Options in several colors, including black
- 11 inch inseam
- Casual enough for errands, dressy enough for date night
Wal-Mart Bermuda Option (T-shirt dress)

After a frustrating battle with dowdy pull-on choices, I spied this little beauty. No, it’s not shorts, but just WOW. At $12.44, this piece definitely meets all my requirements, with a bit of extra style thrown in. Sideseam pockets are extremely flattering and versatile. Size down for this comfy cutie. I went back for another one in grey!

Priced at $37.00, the Penney’s St. John Bay brand short is extremely versatile. It comes in a variety of colors, was very comfortable and had a bit of support at the waist for those of us with a little extra fluff there.

Sorry to say, not one of the “bermudas” on the women’s side of the store fit my requirements, mostly because their longest inseam was 9 inches. I bravely ventured to the men’s side for these slim fit Bermudas for $29.99. The fit is obviously male and definitely not a winner. Let’s step up the game for Moms, Old Navy!
The Athletic Short
I must confess, this is the category I dreaded most. Here are my stringent requirements:
- Flattering cut
- Easy movement
- Neutral color
- Fun detail
Folly to hope for so much, you say. Check it, I found a winner:

My go-to athletic brand for Wal-Mart is Avia, but I couldn’t find a short I liked. This capri, however, priced at $12.96, was wonderful. My favorite feature is a huggy waistband that comes just under the naval. No more worries about the fluff showing when I raise my arms!

This fun little skort for $37.00 was very cute, but didn’t have quite as much mid-section support as I was looking for, so it was a pass for me.
Old Navy redeemed themselves with this $22.99 short. Not only did it meet my requirements, but I needed to size down, always a plus! The side detail is hard to see in my photo, so check out the link.

And the Top 3 Shorts Winners are…
The Jean Short Award goes to Wal-Mart.
The Bermuda Short Award goes to JC Penney.
And, the Athletic Short Award goes to Old Navy.
I hope my shorts adventure saved you some time and dressing room angst this month! Looking for more simple suggestions to up your style? Click on over to this post.
Photo credit: Ethan Hale



Great post! Thanks for sharing!
You are very welcome! Hope you found something you can use.
Great post! We (my sister and I) are in midlife and don’t think shorts suit us at all! Even in the house, it’s a struggle, lol. I suppose it had to do with the way we were socialised but also because we don’t think we have the body for it.
Thanks for your post though, and the shorts do fit you. I personally prefer Bermuda shorts.
Joleisa, I feel you! The Covid pounds have crept on since I posted these photos and I am shorts-shy this year also. Thanks for reading!