How to Wear Shorts Over 50 When You Thought You Couldn’t

Today I’m talking about shorts over 50- a topic I find always stirs up a lot of conversation and divides women into two distinct camps: the ones who like and wear shorts and the ones who wouldn’t be caught dead in them.

There’s a big fear about looking old and frumpy in shorts which is why many of us avoid them, but does it have to be that way? I’ve teamed up with my blogger friends Susan  Une Femme d’un Certain Age , Jennifer  A Well Styled Life, and Tania  50 is Not Old to find out. Here are some fresh style ideas for shorts outfits, starting with this upscale casual shorts look I put together for summer.

Shorts over 50 lack shorts orange jacket

I’m the first to admit I don’t wear a lot of shorts. 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 the last couple of seasons, I thought I would give them a go. I recently ordered several pairs of long shorts to try on and ended up settling with 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.



Shorts over 50 black bermuda shortsI have been seen a lot of shorts suits around – the kind with matching jackets and shorts,  and I quite like the look. But before diving in, I decided to experiment with this orange linen jacket that I had in my closet. ( similar here) To create these chic shorts look, I paired my black Bermuda shorts with a cute leopard tee and added this bright orange linen jacket.  I included a belt to keep the look dressy and slipped on these 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.

Nice jewelry also helps elevate this look. This gorgeous layered necklace is from Dean Davidson, one of my favorite jewelry designers. Check out 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 makes them work really well with the exotic animal print.

shorts over 50 black long shorts

Don’ 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 are almost like a pencil skirt, but more sporty and relaxed. I like the length just above the knee and not too wide of a leg, or your body will look boxy.

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


So there’s 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 some texture like linen, snakeskin,  and straw to make it summery.
  • Beautiful, quality  jewelry elevates the look

Be sure to check out how my blogger friends are styling their shorts too. Visit Susan at Une Femme d’un Certain Age , Jennifer at A Well Style Life,  and Tania at 50 is Not Old to pick up a few ideas that may just change your mind about wearing shorts this summer!


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19 thoughts on “How to Wear Shorts Over 50 When You Thought You Couldn’t

  1. I bought some last week to take to the beach that were bermuda but a denim type biker short from Loft. I rolled them up twice as petite, ha! Added cute tops as the heat index was unreal. 104 to 115 heat index in Mississippi and Alabama. I’m not sure they worked especially great on me as usually stick to ankle length crop jeans in the summer but hey I tried. When I use to wear shorts they were shorter length but turning 70, I was trying to stay age appropriate. Thank goodness I am still a size 2P but I tell myself just because I am small doesn’t make it right to wear. But also I don’t want to look old either. ha!
    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 at all, 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 standout more or look even shorter.

    1. Hi Lisa, Yes it depends on your height and the length of your legs. I 5’7″ and have fairly long legs but if you were short, you’d want to go with something a bit shorter 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 the top & shoes

  4. The shorts are perfect on you. This is the kind I wear too 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 too. 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 as classic, polished and chic! That said; IMHO feel with a few tweaks the pieces could also read sporty, relaxed and casual. 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, switch out the gold jewelry to a/or statement artisan piece(s). Optional: keep the jacket and wear as is or change out to either colour in your handbag. -Brenda-

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