How To Wear Shorts Over 50: Timeless Styles For Classy Ladies

I was recently talking to my blogger friends Susan, Jennifer, and Tania about how to wear shorts over 50 (stay tuned until the end for links to their posts!) We were discussing how shorts is a conversation that instantly divides women. You have the gals that love shorts and can’t get enough of them, and the gals who wouldn’t be caught dead in them.

There’s a real fear of looking old and frumpy in shorts, so many of us avoid them. But does it have to be that way? I have a handful of styling tips on how to wear shorts after 50 that may change your mind about wearing them this summer!

How To Wear Shorts Over 50: Timeless Styles For Classy Ladies

I’m the first to admit I don’t wear shorts that often. I have a couple of medium-length pairs I take on vacation and at the odd time, I will wear them in the backyard. But with Bermuda shorts trending, I thought I would give them a go.

I recently ordered several pairs of long shorts to try on and settled on this pair of black Bermuda shorts, The Amazon Essentials pair in black looked identical and was a close second, but I loved the stretch built into this sleek pair. It made them so much comfier. Now that I’ve introduced you to one of my go-to pair of shorts, let’s look how to wear shorts over 50—and all the things you should (or shouldn’t) be doing!

See more about my opinion on Bermuda shorts in this post!

shop the look

Match With Tailored Tops And Jackets

I’ve been seeing a lot of tailored looks with shorts lately, and I quite like the look. For my own personal spin on this, I styled an outfit with a fun orange jacket and a nice leopard tee. It doesn’t look business-casual powerful, but it also doesn’t look overly relaxed, either.

I wore a belt to keep the look nice and dressy, and I paired it with these fabulous snake print sandals. When you wear shorts over 50, you want the outfit to look intentional. Structured pieces balance out the casual vibe below.

Add Texture Like Linen, Snakeskin, and Straw

When you want a look that feels like you’re doing summer right, add some texture! Layered textures especially feel visually rich and fabulous. Don’t feel like you have to wear tacky-colored shorts or textures that don’t feel personal to you. I went for snakeskin, leopard print, and a sleek blazer for a chic safari feel, but the textures and patterns play with each other perfectly.

And top it off, every gal needs a straw bag in the summer time. It adds a pop of personality without feeling like too much. I love a big woven bag, but you could opt for a straw clutch or crossbody bag and still look just as chic.

Find The Right Shoes

I’ll be honest with you all, I don’t often reach for flip flops. Even when I’m vacation (pool, beach, cruise), you’ll most likely catch me in a cute pair of summery sandals! With that being said, be mindful of which shoes you wear—it can make or break your look when you’re wear shorts over 50.

Because your shorts may lean more on the casual side, you need to dress up your feet with the right pair of shoes. Think more along the lines of sandals, loafers, espadrilles, or even sleek sneakers. Your shoes, like the rest of your look, should feel intentional.

Wear Quality Jewelry

Lovely jewelry from Dean Davidson, one of my favorite jewelry designers, also elevates the look. Have a look at the photo above to see the matching gold stud earrings and chain link bracelet from his Manhattan collection. These pieces have a lot of texture (hammered gold), which works well with the exotic animal print.

You want to skip out on any costumey jewelry, as this can completely throw off a shorts look for a woman over 50. Timeless jewelry is the missing ingredient to make you look WOW!

Get The Length Right

As you can see, the longer shorts make a big difference to the look. These shorts with the 10″ inseam are almost like a pencil skirt but more sporty and relaxed. I like the above knee length; they have just the right leg opening size.

So how do you find which shorts to wear over 50? It all comes down to your figure, body type, and what makes you feel confident. You don’t want anything too short, you’ll look skimpy and unflattering. But you also don’t want anything too long, otherwise you should’ve just worn a skirt, lol!

For more tips on finding the right length and style of shorts, check out this guide.

Be Mindful Of Details

Knowing how to style the small things is what matters most if you plan to wear shorts over 50. Take note of a few things I did in my outfit. I tucked in my shirt, styled with a belt, kept my pieces sleek and unwrinkled, and wore the right accessories.

Can you imagine if I left my shirt untucked, didn’t compliment the outfit with a bag, and came out with a wrinkly jacket? It would look frumpy, disheveled, and like I threw something on and ran out of the door, lol!

Pay attention to the little things, they go a long way!

Will you be adding shorts into your summer wardrobe?

So there are my non-frumpy shorts look that would look fabulous on any woman looking to wear shorts over 50. I call this a sophisticated version of shorts since it’s more dressy with the jacket and longer shorts. To get the look:

• Stick with a neutral color on the bottom, like black, navy, or beige, which is more elegant,  and then have fun with some color up top.
• Go for simple tailored tops and jackets—nothing fussy. Keep it sleek and streamlined.
• Add texture like linen, snakeskin,  and straw to make it summery.
• Beautiful, quality jewelry elevates the look.

If you like a matched set look, check out this linen shorts and jacket set I also love wearing.

My blogger friends Susan (Une Femme d’un Certain Age), Jennifer (A Well Styled Life), and Tania  (50 is Not Old) also shared some ideas for wearing shorts. Drop by their sites to pick up some more shorts outfit inspiration!

Be sure to check out my LTK storefront to see all of my favorite outfit ideas. And, keep up with my blog for each new post. You can also join my private Facebook group, Fabulous After 40 Dressing Room, to discuss your favorite ways to wear shorts over 50. Are you planning to add a pair of structured shorts to your wardrobe this season? Let me know in the comments!

Meet the author

Deborah Boland

Deborah, a former Fashion & Lifestyle TV host and Image Consultant, understands the style challenges women face in their 40s, 50s, and 60s. As the founder of Fabulous After 40, she helps women tweak their chic and embrace fashion with confidence—so they always look and feel amazing.

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