5 Fresh & Easy Ways to Style Shorts Over 40, 50

Whether you’re vacationing at the beach or barbequing with friends in your backyard, the question isn’t, Can you wear shorts over 40 or 50? It’s How?

One easy way to look great shorts at any age is to style your shorts outfit around a theme. For example:

Shorts - Khaki Tie waist

1. Style Shorts as Part of a Safari Theme

You’ll always look polished and pulled together if you borrow from Safari style. Shop for soft, muted earth tones and neutral shades to get the look. This summer, you should have no problem finding these”Out of Africa colors” since Tan, Khaki, black, olive, brown, and rust are always popular. 

To create a Safari shorts outfit:

  • Start with a pair of classic cuffed tan shorts. These have a cute modern twist- a tie front waist.
  • Add a top in a soft earth tone. I like this desert pink tee with the flattering side ruching. 
  • Finish your shorts outfit with a great leather tote and strappy leather sandals. These have an exotic touch of metallic rose gold, which ties into the earthy feel. It’s that easy!
Shorts - Black Cargo, tropical print top

2. Create a Bright, Tropical Vibe

If you like wearing colorful clothes in the summer, a shorts outfit with a tropical vibe is cheery and upbeat.

To create a Tropical Vibes shorts outfit:

  •  Adventurous-looking cargo shorts. I like this chic black pair. 
  •  Add a bright top with an exotic leaf or flower print.
  • Accessorize with straw or rope wedge sandals to go with the tropical island feel, and don’t forget a textured, summery tote to complete the look.


Shorts - Pink Linen, Check shirt

3. Try an Old Money Linen Shorts Look

Linen is a popular summer fabric because it keeps you cool and has a classy, laid-back look and feel.

To look instantly chic:

  • Pair a linen top with linen shorts. I like these pink drawstring linen shorts because they are comfy and feminine.
  • Add a pair of rope and leather espadrilles and a fun, round, rattan bag.
  • Finish with exotic, textured earrings, and you are all set for a stylish summer.
Shorts - White Bermuda,snakeprint top

4. Go Edgy with Snakeprint

Bermuda shorts are trending this summer in a big way, but if you are concerned about looking a little old lady in them (they’ve had that reputation in the past, wear a trendy top.

Trendy Top with Shorts Outfit Recipe:   

  • This sleeveless, button-up snake print shirt is edgy and cool.
  • Add some sexy square toe sandals, which are trending right now. 
  • A fabulous,  soft leather bag rounds out this chic, urban shorts look.


Shorts - Khaki with floral scarf belt

5. Get Preppy with a Scarf Belt for Your Shorts

For anyone who likes more of a playful, preppy look, here’s an idea. Roll up your shorts and tie a scarf around the waistband. These shorts are unique because they come like this, with the scarf built right in.

To get this preppy look:

  • Add a flowy sleeveless shirt
  • A pair of braided sandals and a leather crossbody bag look classic
  • Brown and navy are a very sophisticated color combination that will make any shorts outfit look more grown-up and chic.

Do you have an idea for a summer shorts theme?

Nautical is another one of my favorites. I love the look of a red, white, and navy shorts outfit. How about you?

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24 thoughts on “5 Fresh & Easy Ways to Style Shorts Over 40, 50

  1. Hi Deborah, I accidentally found your website while on the computer. You’ve given me so many wonderful ideas about looking really great. I turned 75 in May and I get so many compliments about what I wear. You give me great ideas to dress looking great yet not looking like I’m trying too hard to look young. Just want to look classy and since I love clothes and shoes this has worked out beautifully. You also give me colors to put together I’d never thought about. Keep up the great work. You’ve made a 75 year old feel really up to date and classy.

    1. Hi Marlene,
      Thanks for dropping by. It’s never too late to look stylish and I’m so glad I’ve inspired you. When you look great, you feel great and life is so much more fun. As I always say, Life is too short to be Frumpy.

  2. I am about to give up on wearing shorts, Not because of my legs, but because of the fit! Current shorts seem to be cut full in the thighs, making me look like I am wearing a box. Denim shorts are the exception, but I don’t want to wear denim all of the time. I know I owned shorts in the past that were narrower in the legs. Are there any brands that offer a slimmer cut in shorts?

  3. I really enjoy your blog Deborah. Thanks for this great post on shorts. At age 55, I thought shorts were a thing in my past. You have given me so many styling ideas. I love that you also link the product to the store.

    1. Hi Mareva, Thanks for dropping by. I’m glad you are being inspired by the blog. I think that shorts over a certain age are not allowed is nonsense. I’ve seen lots of mature women rockin shorts of all kinds. If you want to wear them, why not? I think the key is to put together a complete short outfit to look a little more polished, sporty and modern. Sounds like you are doing that. All the best and please let me know what you’d like me to write about. Cheers, Deborah

  4. Deborah – Do you feel there is a rule regarding length after 40? I will be 45 this summer and am in the best shape of my life – even better than when I was a 4 sport athlete as a teenager. I am a fitness competitor and have found the shorts in the “mature” section of stores do not fit me at all. The proportions from waist to hips is always awkward in those sections. I don’t want to look like I’m trying too hard to be young, but I REALLY don’t want to look like a frumpy, soccer mom either. Any suggestions?

    1. Hi Jodee,
      I like shorts with a 4 inch inseam or more. That’s short but not skimpy especially if you get more tailored shorts. Banana republic always seems to have lots. I think it also important what you wear up top. If you are going for short shorts, go with top that doesn’t show as much skin. It’s that balance that will make you look classy not trashy. Here’s an article that will give you a few more tips:

  5. thanks for fixing the Basic Black and White for the shopping information – – Love, love this outfit for Summer
    I guessed the shoes were Toms but was not sure about the res..

  6. I love shorts, but have a hard time finding ones that fit. So last summer I opted to wear stretch capri leggings with a longer top. Works great for me. Also has the benefit of being more comfy than bottoms with a woven waistband. But if I find shorts to fit, I’ll gladly wear them!

  7. Hi Deborah, the styling-tipps are great. Your photos are always a good Inspiration. The color mix of the styles is so beautiful. My leggs are not so good in form, that I could wear a short – with 55 it’s not so easy. Greetings Martina from Munich

  8. I’m 43. Others say I look like 29, cuz I am 5’2 feet, 29 inch waistline, I can wear shorts,skirts and mini dress which are comfortable for me!!!! and I look too pretty so others say!!!

    1. I agree. We live in Florida and it is too darned hot to wear long pants all summer. We see a lot of maxis in gauzy fabrics, sundresses, skorts (tennis and golf people), and knee length skirts as well as shorts. I think the key is stated here in the blog advice. Stay toward the more tailored (dressy) shorts versus the Daisy Dukes. A pair of shorts that hits mid-thigh length is flattering, not cheap looking. They also peek out of the bottom of a longer (covers the derrière) top worn untucked. A pair of heels can dress up shorts, but flat sandals look great all year long here in FL.

  9. I say opt for a skirt instead of shorts! They are so cute- and much cooler (meaning a little more breezy). You can pair a cotton skirt with flip flops and a tank and look stylish! Now that it’s fall- this conversation may be a little late… but had to add my 2 cents!

  10. Go Kim! Wish my husband liked it when I wear sexy…..think he’s more jealous than anything but he sulks the minute I try to look sexy! You wear your shorts and keep looking good,feel good when your man tells you this! Enjoy! I envy you! I look good but hey,this man of mine likes to peep at the other woman,some even far more dam ugly than me but hey, we can sit in a public place and he will make me feel like i’m the ugliest woman alive though I know i get looks from other men, some even younger than me! You go girl!

  11. Hi, i turn 50 this year. I am still in good shape though i never like wearing short skirt or shorts. I need a change, i like to wear fashion items and looks younger than my age, i also like to try out different or new ideas. This winter i bought myself some leggings which i wear only with a long top, jacket or jersey with boots. I must admit,it looks good and i feel good. The other day “something came over me” and i bought myself a short short in denim and also a very short skirt which i tried on with my leggings and boots, it looks really good though i will never go outside because i feel it’s not appropriate for older women. I really want to wear this style though with a long jacket, cover up of course when going outside. You may ask “why do i bother then”? Well, this is to feel good for myself,i don’t want to show my nice legs and sexy clothes out there, i want to know inside, and feel, that i look sexy for me. Am i weird? Hope not but if i do,are there any women out there that does these kind of things? I always try something new,not always proper for my age but hey, what the heck, if i feel good then stuff the rest right? I cover up anyways when outside the home,what does it matter what i look like underneath a pretty coat? I’ve always been a dark head gal,started turning grey the same age most ladies does, i hated it, then started to dye red,black,brown and any other colour one can think of. Recently i started to like the grey fashionable look, decided to go through the whole proccess in turning from red to blond, then to grey eventually. Still reshearching on this but it will come sooner than later. Why do we have to look like a granny if there’s still a lot of spark left in us? I get looks from men and even from woman…..but not good one’s from woman but i also don’t care. My own husband is very old fashioned concerning their woman,just like his father,etc though i see the looks he gives other sexy woman but he turns quiet and sulky when i look good,young and sexy! I hate this and one of the reasons why i feel i need a change,for myself and not even to spite him but just for me and me alone! Careful, thinking of getting a tattoo in a very classy manner,somewhere neat, not tacky and cheap though stylish,small yet still there to make a statement. What do you other gals think of my ideas?

  12. Im just a little bit over 40.My legs are in pretty good shape so I do like to where shorts on the short side. My husband likes me to where high heeels with them so I make him happy.

  13. Nice tip about shorts – Unfortunately in Australia it’s hard to find shorts that are good for over 40 Ladies. Most styles sold are for the very young, unless you want the ‘granny version’ – elasticised waist in pastel colours! Yuk! Any Aussies who know a good place to find over 40’s shorts please let me know.

  14. Shorts at 40, just to or above the knee may be ok, but for me, at 56, that length just highlights what age has done to my knees. Either shorter (several inches above the knee) or covering the kneecap/just to the top of the calf is much better – which technically I guess are not shorts! (I have very long legs, so the longer length works). To wear the shorter look, I’m finding that a skort (with the ‘skirt’ part in front and back, not just the front) is more flattering & just as easy to wear as shorts – & easier to shop for.

  15. Hi Deb, Just had to say Hi and note that it was amazing how my first summer after turning 40, shorts are suddenly an issue! Thanks for your advice. Looks like I have some shopping to do.

    –Amy Tiemann

    1. Hi Amy,
      LOL!!! Great to hear from you and to hear your finally old enough to be official! Glad you found my advice helpful. Ie want you to still have your mojo with your wardrobe!

  16. Hi Deborah,

    Just a quick note – I really en-JOY reading your tips over 40! I find them incredibly helpful, practical and inspiring! Keep them coming!!

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