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How to wear shorts when you’re over 50



How to wear shorts when you're 50+

“I can’t wear shorts, I’m too old for that”

It’s a comment I hear often from women over the age of 50 (and sometimes over the age of 40!)

They feel that hitting a certain number automatically takes away their right to wear specific types of clothing. Well folks, I’m here to tell you that it just isn’t true.

Saying you can’t wear shorts over a certain age is just as ridiculous as saying someone over a certain size shouldn’t wear a swimsuit.

I understand that you want to look age appropriate, but I have a little secret for you. It’s possible to wear shorts at any age and look age appropriate.

Here’s how.

1. Choose the right length

Obviously, you don’t want to wear daisy dukes, but just because you’re older doesn’t mean you have to wear Bermuda shorts. Finding the right length for your body is key to looking age appropriate in shorts. Essentially, you want your shorts to be no higher than where the inside muscle of your leg ends. To find that spot, stand in a superman pose with your legs slightly spread. The inside of your legs will get thinner as they go from your pelvis to your knee. Whenever they stop getting thinner and just go straight down, that’s where the muscle ends. Here are several pictures featuring women of different body types and shapes. The red line is where the inner muscle ends (and where your shorts should begin).

From left to right: Ashley Graham, Goldie Hawn, Julie Andrews

2. Keep it simple.

Leave the bright floral prints, polka dots, and stripes to your kids and grandkids. Opting for neutrals like white, beige, black, and navy are going to look more classy than cutesy. It’s also a good idea to choose shorts from more structured fabrics like thick cottons and canvases. These fabrics don’t wrinkle as easily, they don’t cling to your skin, and they look more pulled together (aka: age appropriate!) than linens and slinky polyesters. Keep it simple when it comes to pockets, too. Cargo pockets look bulky and will make your legs look bigger than they are. The more hidden the pockets, the better. If you need help coming up with a classic wardrobe of clothes, click here.

Washed Chino Bermuda ShortsWashed Chino Bermuda ShortsWashed Chino Bermuda Shorts7" Button-Hem Short Riviera Shorts with 6 Inch Inseam color Coral Blush

From left to right (LLBean, Eloquii, Talbots (other colors available), LOFT (more colors))

how to wear shorts and not look frumpy

3. Choose the rest of your outfit wisely.

If you’re showing more skin on your bottom half than normal, cover up more on top. A cardigan or long sleeve shirt will keep you from looking like you’re baring all. Also, try to pick tops that match the formality of your bottoms. In other words, if you’re wearing gym shorts, wear a t-shirt. If you’re wearing tailored khaki shorts, opt for a nice blouse (like a button down oxford). Pair nice shorts with the same tops you would wear with business casual khaki pants.

Here are several ideas of how to wear shorts:

outfits with shorts

Left to right (Casual daytime look, more professional look, very casual/beach look)

Creating a wardrobe of clothes you love can be hard, not to mention when you’re trying to achieve an age appropriate look. If you’re looking to boost your style (or even start out in the right direction) keep reading here about my classic wardrobe basics (and the 20 items that make up every great wardrobe- no matter how old or young you are).

How do you wear your shorts? I’d love to know! Comment below. 

xoxo, Leslie


  • Mary Lou Moreno

    July 5, 2019at4:51 am Reply

    Hello, I’m 52 years old and I have enjoyed reading this whole article. I wear a whole lot of Boom Boom shorts that I buy online from a website called Poshmark, but now that I’ve read your article it has changed my way of wearing shorts.
    Thank you

  • BarbaraTennyson

    July 23, 2019at2:11 pm Reply

    Thanks! I’ve not worn shorts for 10 years, but have recently decided (at 73), that it’s ok again. Maybe I’m past the age of worrying about being attractive, but I do want to look neat and stylish, your article has helped me tremendously! Thanks

    • leslief

      September 23, 2019at10:47 pm Reply

      So glad it was helpful!! Thanks for sharing. 🙂

      • Robin Simpson

        March 22, 2020at9:39 pm Reply

        You are Never too old to care about being attractive! Just too old to worry about what people think. As long as you are wearing clothes that are age appropriate, and you like what you see, that’s all that matters!

  • Brenda Lusk

    August 6, 2019at1:02 am Reply

    I agree with almost everything about this article. I do believe under the right circumstances the printed shorts work fine for myself and other slim and fit older women. They work great with solid top or sweater. Dressing appropriately for ones âge is very important for a positive self image

  • Vicki Doris

    August 9, 2019at4:50 pm Reply

    Hi! I’m 66 and just bought a pair of white thick cotton shorts ( nothing show through). I hadn’t worn shorts for quite some time and worried about how I will look. The shorts are fairly long, not quite to the knee. I was planning on wearing a quarter length sleeve tee shirt. Your article was very helpful in reassuring me I was choosing wisely! Thank you!

    • leslief

      September 23, 2019at10:50 pm Reply

      So glad it was helpful; I appreciate you letting me know! And, I’m sure you look wonderful in your new shorts. 🙂

      • Lenee Jones

        June 7, 2020at10:08 pm Reply

        I’m a very fit, athletic, healthy and muscular 55 year old woman
        I’m one of those bodacious ladies who will continue to rock 3 inch shorts when going to the gym or when I just want to wear a pair of shorts. Life is too short to be pigeonholed in a box; instead, I wear what makes me look and feel great.

  • Karin A

    August 12, 2019at1:05 am Reply

    57 and went 20+ years not wearing shorts. I’ve worn shorts all summer long. Mostly pair with summer sweatshirts. I like the long sleeve with shorts look, feel more covered up but feel cool and trendy.

    • leslief

      September 23, 2019at10:54 pm Reply

      I LOVE the look of long sleeves with shorts! My favorite weird outfit is a button-down oxford from Ralph Lauren and Nike gym shorts. It’s not the most fashionable long sleeve, short combination, but it’s a classic for me while I’m just lounging around the house.

      I’m glad you broke your 20+ year stint and started wearing shorts again! I’m sure you look fabulous!

  • Mezata

    August 12, 2019at4:13 am Reply

    Bonjour,ma femme est + 50 et adore mettre les shorts je dirai sexy,et ça lu va bien,et c est une deuxième jeunesse,

  • Melissa Hayes

    August 23, 2019at8:39 pm Reply

    I wear white cotton, or denim shorts. Look just like jeans but are.shorts.and my length is about where you recommend. You are never too old to wear something. I am 51 by the way.

    • leslief

      September 23, 2019at10:57 pm Reply

      I completely agree that you’re never too old! I’ve met so many women that say they can’t wear shorts (and their age is the only ‘excuse’). Thanks for breaking the horrible myth that you can’t wear shorts (or anything else!) after a specific age.

  • Lorena Varela

    September 2, 2019at5:25 pm Reply

    I just turn 60 and love wearing shorts, get compliment on my legs. I always had strong healthy legs and I’m not shy about it. I don’t wear the shorts too short.

  • Anne smith

    September 10, 2019at3:22 am Reply

    I have discovered shorts. They are very forgiving,

    • Anne smith

      September 10, 2019at3:24 am Reply

      Scorts is what I ment

    • leslief

      September 23, 2019at10:45 pm Reply

      Yes! I think skorts are such an underrated piece of clothing. All the comfort of shorts but the classiness of a skirt- it’s a win-win situation. Thanks for sharing! 🙂

  • Dynetta Robinson

    September 17, 2019at2:07 pm Reply

    I’m 62yrs young.And was always self consciousness about my skinny legs.,however my 66 yr old friend who wear shorts all the time recently encouraged me to begin weraring shorts (according to her my legs are nice) I love wearing shorts and now have 2 pairs and 2 jeans short skirts

    • leslief

      September 23, 2019at11:01 pm Reply

      I’m so glad you got back into wearing shorts again! I also have skinny legs (I call them chicken legs) and I think that people don’t always realize that being skinny can cause similar anxieties to being overweight (or whatever aspect of your body makes you insecure). I used to be terrified of looking like a popsicle, but now I embrace it. In fact, maybe that should be my next blog post: In defense of the popsicle. Thanks for the inspiration!

  • MLP

    November 8, 2019at4:18 pm Reply

    Loved reading this as I started wearing shorts again around age 55 (I’m now 58). I always thought that capri pants were more “tasteful” but figured out that they really don’t look good on anyone! I’m 5 feet tall and it was so hard to find ones that fit and looked good. I love wearing shorts that fall a tiny bit above my knee, I think they are so flattering.

  • Liz Tompkins

    March 4, 2020at2:25 am Reply

    Hi my name is liz I’m 67 wear my 3 in shorts every day im crossing guard so it’s very hot in the afternoon work at gap weekends they have fantastic shorts 3 and 5 in all different colors and floral if you like t shirts and some nice shirts to love wearing my shorts I’ll still be wearing them when I’m 90 ha ha one love ❤️

  • Stacie Kreitman

    March 10, 2020at12:47 pm Reply

    I wear shorts all summer long because otherwise I would be too HOT. I think showing a little leg beats showering 5 times a day. LOL.

    • leslief

      March 30, 2020at7:42 pm Reply

      Haha. I agree!! One of the main reasons I wrote this post is because I knew women who said that you couldn’t wear shorts over a certain age. Not true!! You can wear shorts as long as you’d like…it sure does beat showering 5 times a day. 😉

  • Nancy

    April 22, 2020at4:06 pm Reply

    Wow, I’m 85 and have always worn shorts at about the length you have recommended. Reading about women in their 50’s and 60’s not wearing shorts was sad.
    I also have seen women who never should wear them…..obese ones particularly.
    I’m 5’9″, wear size 12 and there you go…….onward and upward, ladies!

    • Kat

      July 31, 2020at11:27 am Reply

      I am a 56 year old woman who also happens to be overweight. I wear shorts. Yes, even those of us who medically are considered “obese’ can classily wear shorts. Length is important to me as well as color. I agree that fabric is key too. Hope this helps the other beautiful women out there who have weight issues and are self conscious about how they look.

  • sharon maurer

    May 21, 2020at5:45 pm Reply

    I’ve never stopped wearing shorts, I’m 78 and lead an active lifestyle. Once I moved to Florida and discovered you could wear tennis clothes to the grocery store I’ve never looked back.

  • Elaine Penn

    May 24, 2020at4:13 pm Reply

    I live in the tropics. Only in the coolest winter months are jeans even an option for me. I’m now 72, average weight and height, and wear Bermuda or walking shorts year-round, or knee length trouser skirts. My go-to tops are basic solid loose fitting tanks like the Lands End staple cotton tanks. Comfortable, forgiving, easy care and age appropriate for our climate and lifestyle.

  • Sue

    May 24, 2020at5:02 pm Reply

    Nice article. I’m soon to be 64 and have never stopped wearing shorts. I’m very active with walking and golfing. I cannot image how hot I’d be without shorts! So, as I was reading this, it made me sad….have you seen the gross older men wearing shorts? Not to mention when they go shirtless! LOL! It’s a shame women feel the way they do. Or society has made them feel this way? I wear a size 6-8 but no matter what size I have been in life, I couldn’t live w/o shorts. I feel good about my age appropriate length.
    I will say I went to visit my 84 year old art teacher who was wearing shorts and she looked great!
    I even commented to her that she has great legs!
    If you’re comfortable WEAR them ladies!

  • Dorie

    June 6, 2020at5:24 am Reply

    Dorie June 5 2020
    Hey gals over 87 + and love skorts and walking shorts. Only 130 pounds so I can wear gracefully. Shorts can be very classie and sooo comforable. Also flat heels are attractive with them. Add some color and go shine,ladies.

  • Renee Bryant

    June 8, 2020at10:27 am Reply

    Hey I’m 52 and you know what? I look GOOD !! I wear regular length shorts, not to long not to short… But really, I could give a damn what people think! Confidence is key! Wear those shorts ladies!

  • Glenda Jo Martin

    July 20, 2020at7:54 pm Reply

    Ladies, wear whatever makes you feel comfortable. Life is to short to worry what others thinking you should wear for your age.

    At 72 years young I still wear walking shorts. Usually, a nice outfit with solid color pants and a print top.

    My late husband always said to me to take a complete view of myself before I leave the house. I still do this routine daily at my entry hall mirror.

    Remember, “Touch your toes, if anything shows go change your clothes “. Good comment to remind our granddaughters.

  • Christina

    July 29, 2020at12:28 pm Reply

    Hi, I am 58 and have a athletic thin body. I wear and will continue to wear my 3” shorts as they make my still fit legs look the longest. Age is number, confidence and mindset is always in style.

  • Paulette Melanson

    August 11, 2020at1:07 pm Reply

    Chiming in on Summer Shorts at 68. I live in N.H. so our summer is relatively short. I retired in January and with quarantine I’m learning a new way of every-day dressing at home. I have been wearing exercise/walking French terry shorts and casual skorts and skirts (all appropriate length for my legs and age) with sleeveless and short sleeve tops around the house and doing groceries. I do own one pair of white cuffed shorts that are my favorites with anything I pair with them. White is my preferred color as it goes with everything. Seems to me I should find another pair or two while everything is on sale!
    PS – My legs have always been one of my assets and continue to be, so I enjoy wearing skirts and shorts as much as possible.

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