Blonde woman walking down stairs wearing black blouse and tan shorts.

Blonde woman walking wearing black blouse and tan shorts.

Blonde woman standing against column wearing black blouse and tan shorts.

Wearing shorts in midlife, especially over 50, can be daunting! We all want to feel cool and comfortable, especially in the warm summer months. However as we age, wearing shorts can become less flattering and simply discouraging. Our legs can begin to look crepey, with less muscle tone, and we might not feel confident.

Today let’s up our shorts game with 5 styling tips you can easily follow plus an introduction to a brand made for all shapes, sizes and ages (and a discount code).

Also, I’m partnering with them to gift a $100 gift card (and denim tote) over on INSTAGRAM (scroll down to learn more).

5 Styling Tips To Look Chic In Your Shorts Over 50

 1.  SIZE UP

I always suggest wearing your shorts a bit over-sized. A middle-aged woman should NEVER wear shorts that are too tight or too short. Shorts look best when sized up at least one size. No muffin top ladies and sizing up makes the leg opening wider which helps make your thighs look smaller. Above all, your shorts should fit properly….. meaning not too baggy but not too tight either! And don’t forget to take a peek at your backside!!!!


A middle age woman should never wear shorts that are too short. When in doubt, the finger tip test is a good rule of thumb. Put your arms down by your sides. If your shorts are WAY shorter than the end of your fingertips, you might want to opt for a longer inseam. I like shorts that hit at mid thigh. You want your legs to look long and lean and this length will help with that. My linen shorts have a 9″ inseam.


Having more volume on top will give the illusion of your lower half looking slimmer. This helps create balance in your look by not having everything on your body form fitting.


The shorts I’m wearing have an 10.5” rise, so they’re high waisted and make your legs look longer, which is quite flattering. Anywhere from 9” to 12” inches is considered high rise.


I don’t like to look super tan but I do like to have a nice, healthy glow in the summer. I DO NOT lay out and I rarely get spray tans because I just don’t love the smell. This bronzing and slimming shimmer by Charlotte Tilbury is the super model’s trick to create an optical illusion of longer, leaner limbs and firmer contours!!!  All the Victoria Secret models use it. Try it…you will thank me! A glowing body looks gorgeous in shorts.

NYDJ Apparel:

NYDJ, formerly known as “Not Your Daughter’s Jeans,” was founded in 2003 to address a gap in the women’s denim market. Since then, their mission has grown to address women’s head-to-toe style needs, while staying true to a fit-first mindset, as a lifestyle brand they can depend on to discover style their way. Made for all shapes, sizes and ages, NYDJ’s selection of clothing, handbags and shoes is designed and carefully curated to complement their customer’s every move and help her express her style point of view.

25% off sitewide with code: Megan25
○ Code Exclusions: Gift Cards, Forever Comfort, some Statement NYDJ products, and Fab Fit Fun.


Be sure and head over to my INSTAGRAM page where I’m partnering with NYDJ to give one lucky follower and a friend a NYDJ Denim Tote + a $100 Gift Card!

What I’m Wearing:

The 5 Pocket Bermuda Shorts in Stretch Linen by NYDJ have a sleek, classic appearance that makes them easy to dress up or down from season to season. With NYDJ’s exclusive Lift Tuck® Technology these flattens your front, using a proprietary slimming panel with a patented criss-cross design for the best fit ever. These shorts come in several colors! Wearing a size 2. Code: MEGAN25 saves 25%.

I’ve styled them with the NYDJ Flounce Sleeve Blouse in black. You’ll be floating through warm days in this easy silhouette that pairs perfectly with your favorite shorts or jeans. Wearing a size SMALL. Code: MEGAN25 saves 25%.

My Black & Bronze Arabesque Slides are on MAJOR SALE! They are an effortless and comfortable slide for vacation and come in other color ways. Code: SARAHFLINT-BATRULYMEGAN to save $60 off your first pair of Sarah Flint shoes!

Hover & Shop:

Thank you for reading~

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Shorts Over 50