A Classy Way to Wear Shorts Over 50

Today I’m talking about shorts over 50 with my blogger friends  Susan, Jennifer, and Tania.  Shorts is a topic that always stirs up conversation and divides women into two camps: those who like and wear shorts and those 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? Check out this chic way to wear shorts over 50, and let me know if it changes your mind about wearing shorts this summer!

Shorts over 50 lack shorts orange jacket

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 from NYDJ.  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.


shop the look


Shorts over 50 black bermuda shortsI’ve noticed a lot of suits around – shorts with matching jackets,  and I quite like the look. However, today I’m experimenting with this orange jacket that I already had in my closet. ( similar here) I’ve paired my black Bermuda shorts with a cute leopard tee and added this relaxed linen jacket to create a chic shorts look.

I’m wearing a belt to keep the look dressy and these fabulous snake print sandals. Then, I picked up this cute straw tote to give this outfit a breezy warm-weather vibe.

Shorts Over 50 black

Here’s a better look at that tee. It’s just a simple scoop neck tucked into my shorts. I thought the leopard print went well with the black and orange, and that safari feel is always so summery.

Shorts over 50 outfit

Lovely jewelry from Dean Davidson, one of my favorite jewelry designers, also elevates the look. Have a look at the photo below 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.

shorts over 50 black long shorts

Don’t forget to push up or roll up the sleeves to give the outfit a youthful, sporty feeling. 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. When the leg is too wide your body can look boxy.

Shorts over 50 straw bag

Here’s that bag. I love switching from leather to something like this in the summer. It gives an outfit so much personality.

Shorts over 50 straw bag 2


So there are my non-frumpy shorts look. 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. Or I have casual, classy shorts outfits ( with no jacket) for you to look at too!

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

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19 thoughts on “A Classy Way to Wear Shorts Over 50

  1. I bought some last week to take to the beach that was Bermuda, but I am a denim-type biker short from oft. I rolled them up twice as petite, ha! I added cute tops as the heat index was u eal— 4 to 115 in Mississippi and Alabama. I m not sure they worked exceptionally well on me, as I usually stick to ankle-length crop jeans in the summer, but I tried. I wear shorts; they were shorter in length but turning 70; I was trying to stay age-appropriate. Ank good s, I am still a size 2P, but I tell myself just because I am small doesn’t make it right to wear. t also don’t want to look old either. H!
    Your short outfit looks great on you!

    1. That’s great to hear, Bonnie. I think denim shorts can look work any age if you feel comfortable wearing shorts. It all depends on the style of the shorts. Short, frayed denim shorts are way too junior and not classy, but it sounds like the ones you bought were more classic and paired with a great top. You rocked those shorts, Bonnie. Congrats!

  2. Well, as most of us get shorter with age, the longer shorts make our middle stand out more or look even faster.

    1. Hi Lisa, Yes, it depends on your height and the length of your legs. I’m 5’7″ and have relatively long legs, but if you were short, you’d want to go with something a bit faster to make you look taller.

  3. I am petite-sized, & shorten most of my capris to around knee length. I can wear them golfing or out for a nice dinner with a change of top & shoes.

  4. The shorts are perfect for you. This is the kind I wear and the only kind I am still comfortable in.

  5. You look fabulous in these shorts! Dressing them up would be the only way I would feel comfortable wearing them. I love the idea of a shorts suit—fun and classy.

  6. You look fabulous in this outfit. I had on that leopard tee yesterday with jeans and a red blazer. It is very versatile.

  7. Loving this look like a classic, polished and chic! That said, IMHO feels, the pieces could also read sporty, relaxed, and casual with a few tweaks. i.e., Roll up the shorts to create a cuff (and shorten), apply a half-tuck to the T-Shirt, add a textured skinny belt and a pair of sneakers, and switch out the gold jewelry to statement artisan piece(s). Optional: keep the jacket and wear it as is or change it to either color in your handbag. -Brenda-

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