Feel Good Ways to Wear Shorts After 40

Not all middle-aged women are comfortable in shorts, and that’s perfectly o.k.  But if you want to wear them, there’s no rule or reason you can’t. Here’s how to pull off shorts at 40, 50 and beyond and feel good about it.

shorts over 40 tan with animal print tee Deborah Boland

1. Choose a Flattering Length

How short is too short when you’re middle-aged or more? Determining the best length of shorts to wear is always tricky. It basically boils down to three things – your figure, where you plan to wear your shorts, and your confidence level. The three most popular lengths are:

  • Short Shorts

These are easiest to wear when your legs are very toned. Aim for short shorts with an inseam that is minimum,  4″ -5″. Anything shorter will look skimpy and unflattering on a grown-up gal.

Shorts striped

similar shorts here with 5″ inseam

These short navy &  white striped shorts I’m wearing (above), have a 4.5-inch inseam. They’re definitely on the short side, but they work. They would look nice at a backyard BBQ, a trip to the beach, on a boat.  I’m wearing them with a sleeveless button-up blouse, rather than just a t-shirt, to upscale the look.

  • Medium Length Shorts

This is one of the most popular lengths of shorts for women over 40. When you don’t want to reveal too much leg,  but you also don’t want to wear Bermuda or walking shorts, then choose a medium length short.

Medium length shorts have a 5-10″ inseam and end a few inches above the knee. This pair of navy nautical-inspired shorts wide the side pocket buttons has a 5″ inch inseam.

Shorts Outfit - Peach denim Bermuda shorts and white tie top styled by Fabulous After 40


  • Long Shorts

Classic Bermuda shorts that end at the top of the knee are a great choice if your legs are not as firm as they used to be, or you need a pair of shorts that are a little more formal.  Bermuda shorts usually have an inseam of about 11 inches. These are a good choice for women over 50, who feel more comfortable with lots of  leg coverage.

Tip: If you’re still unsure about what length to wear, try this trick. Lay your arms down by your sides. Where do your fingertips end? That’s usually a comfortable minimum length for wearing shorts for most women.

Shorts Outfit for over 40 - Blue striped shorts and yellow top


2. Don’t Wear Tight Shorts

Tight shorts, especially in the thighs, are aging and all too common. If you have side pockets, they lie flat. If they flare out, your shorts are too tight.

How to Wear Shorts Over 40 - peach blouse, black shorts outfit styled by Fabulous After 40

3. Buy Quality Shorts

Even a relaxed, casual pair of cotton shorts should look classy and fit well. You can never go wrong with crisp, tailored shorts that look classic and chic. These high waist shorts with the tie are trendy at the moment. Soft, silky shorts can also look classy on the right figure.


chambray shorts, mid thigh denim shorts , cut off shorts (too jr!)


Shorts - Frayed Denim


As for denim shorts for women…

          • A dark wash jean is dressier and more slimming.
          • Chambray is modern but looks more relaxed.
          • Stay away from short, faded, distressed, or frayed cut off jean shorts for women ( Daisy Dukes).

4. Don’t Wear Skimpy Tops with Your Shorts

You want to look classy, not trashy. If you are showing off a lot of leg, then it’s best to stay a little more covered up above the waist. A skimpy top and short shorts start to look tacky over 40. Balance it out.Shorts - Olive Green


5. Wear Fabulous Accessories with Your Shorts

Shorts and rubber flip-flops + not much else looks plain and junior. Add fab jewelry, a great tote,  cute sandals, and you’ve got a grown-up ensemble.

The bottom line is that shorts for women over 40  look great when you put a little effort and thought into your overall look! For more ideas on how to wear shorts, check these tips for  Cute and Classy Ways to Style Shorts.

Rock a great pair of shorts from Amazon.

Top Row: Left | Middle | Middle | Right

Middle Row: Left | Middle | Middle | Right

Bottom Row: Left | Middle | Middle | Right

Who has a great selection of shorts right now?

TALBOTS – They have tons! Lots of Bermudas but shorter ones too

NORSTROM  -An excellent modern selection

CHICOS – A colorful selection of long and shorter


Join the Conversation

63 thoughts on “Feel Good Ways to Wear Shorts After 40

  1. So glad I found this blog!!
    Although, I have to disagree with being able to wear the same shorts at 20 yrs old. At least for some women. If you are blessed with the same figure for 20-30 years kuddos… but most are not and that is ok. Granted, some 20-30 somethings should not be wearing what they are wearing either.
    Thanks for the examples of different lengths and the accessories with them!! Love your style!!

    1. Hi Jessica, This is such a touchy topic with women that no matter what I suggest someone is! I think you are right. It boils down to common sense. It’s not so much about age as it is about your body and your attitude. You just need to find a pair that flatters your figure, and that I would say that is more on the classy side. (ie:leave ripped, frayed jean shorts for teens!) I think if you keep these two things in mind, then shorts can be worn at any age, (if you feel comfortable in them) Cheers, Deb

  2. How to wear shorts after forty….hmmm. Let’s see….put them on one leg at a time, then fasten the button and zip them up. Same as you wore them at thrity, twenty, etc. Age doesn’t make any difference in what you “should” wear.

    1. You are right K, you should wear what you want, but if you want to look your best you need to use some common sense too. You may need to make a few tweaks to look chic and ageless.

      1. Totally agree…just like you shouldn’t be wearing the same hairstyle…you need to change your clothing style as well.

  3. Thank you SOOOO much. 1st of all, I have always despised shopping, even as a teen. And secondly, I’m a youth advocate & activist for their safety and well being. Needless to say being around them all of the, I look them, talk like them, social media like them, but turning 40 last year didn’t seem to register to my brain. I mean I knew I needed to begin scaling back my punk rock attire I’ve always loved and worn, but I wasn’t going down without a fight. I am nowhere near ready for Dress Barn or Lands End and going to the beauty parlor for my once a week football helmet perm. NOOOOO WAAAAY. So I have literally worn nothing but leggings / sweatshirt combo & pajamas for an entire year. Thank god, I work from home. LOL. Anyway this article has definitely helped and pointed me in the right direction. Have a lovely and brilliant day! ~Ambereve Ginunas

  4. Lovely collection! Sorts are one of the most versatile summer staples that belong in everyone’s wardrobe. These shorts looks are so cute and stylish. I want to try them. Thanks for sharing.

  5. Any suggestions for a 4ft7” lady with a few curves, what will suit and what to avoid please.

    1. Hi Elaine, If you are short, you don’t want long Bermuda type shorts because you will just look shorter. Also if you have curves stay away from very tailored shorts. I would go for a looser flowy short in soft material that follows your curves and is shorter rather than longer. There are a lot of cute shorts like that out there this summer. I hope that helps.

  6. Really good tips! I like the one about laying your arms down to see the length of short you would wear – It was almost bang on for me! Thanks!

  7. Hey Deb,
    LOVE your articles! I have struggled with finding shorts the perfect length for my leg length. I don’t want shorty-shorts but Bermudas are too long and make me look “cut-off”. I like the tip about laying your arms by your sides to get the perfect length. How easy! Also, you look great in shorts, but self-tanner makes everyone look better!

  8. Hello, Looking for links to the clothing. Especially the open shoulder cream look. Where do I find these?
    Thank you!

  9. Hi Deborah.
    Thank you for your post. However, all women should have self love and wear whatever they want. To say that only women with toned legs should wear shorter shorts is to say that other woman aren’t as beautiful exactly as they are. If one were to take what you said to heart, then larger gals would never step out in a bathing suit either. All sizes and shapes are beautiful and no one should be judged for their less than toned legs, at any age. Keep in mind that many are dealing with illnesses and medications and perfectly toned legs may not be possible or even what is important. Wear those shorts ladies!

    1. Great post and I totally agree. I’m 46 and I still rock a shortie short. I’m not going to have any person tell me that I have to change the way I like dressing just because I’m a certain age. Wear whatever makes you happy and look good. . . period.

    2. Hi Teresa, I agree with you that all women are beautiful just as they are and should wear whatever they like regardless of age or size. In the article I say, there is no rule or reason women over 40 can’t wear shorts. I find the shorter shorts are most flattering on women (of any age or size) whose legs are more toned. That doesn’t mean thin, it means fit. However, anyone is free to wear short shorts, period, toned legs or not. I’m not the fashion police. Thanks for joining in the conversation.

      1. The older I get the more difficult it is to know what works. Thank you for this website and all of your great tips! Keep up the good work!

  10. Deborah, Thanks for a great post! Your 5 tips to wearing shorts after 40 are spot on. It’s interesting to read ithe responses in the comment section. I can’t remember seeing such a wide variety of opinions on a subject before.

  11. All of these looks are great — beautifully paired and classy. However, I am also one of those women who look better NOT wearing shorts. It’s not just the spider veins and cellulite, but the shape of my legs isn’t great and shorts only serve to cut me off and make me look dumpy. I’m almost 63, but I do try to dress in fun, cooler outfits in the summer … I wear capri leggings with short dresses and longer tunics in cool fabrics; peasant tops with cute sandals; maxi dresses and skirts in light, flowing fabrics.

    That said, if you’ve got the legs — no matter what age — shorts will look great on you. It’s best to know how to accent your best features and qualities, and not show off the less attractive ones.

    1. Less attractive Cyndi? whose standards? I’m sure you look beautiful and can rock whatever you want to wear.

  12. Wow, I’m 60 and it never occurred to me not to wear shorts. Forty? That’s so young! LOL

    That aside, I think the advice in this column is spot on. Nicely written.

    1. in Florida, it never occurs to anyone not to wear shorts… Casual state overall for everyday dress; even the police wear shorts, so if the police can wear summertime shorts, so can we!!

  13. “If you’re still unsure about what length to wear, try this trick. Lay your arms down by your sides. Where do your fingertips end? That’s usually a comfortable minimum length for wearing shorts for most women.” BEST ADVICE EVER. I measured by this guideline & my favorite shorts end right at my fingertips. Add that a touch of concealer or BB cream can make any spider veins less noticeable too – not just for your face anymore.

  14. You got great legs! I envy you and others who can wear shorts. I am one of those people who were not blessed with great legs (got deep scars when i had an accident when I was in my teens). I usually wear long skirts and capri, even if I’m just 5’2″. My husband says nobody cares if i have scars, just wear shorts if I want. I wish I have the confidence.

    1. Make up an outlandish story of how you got the scar ( I had an ACL reconstruction but I tell people, while maintaining a straight face, that I got in a knife fight) and flaunt them. Everyone has scars: they tell your life stories and speak to your resilience and survival.

    2. Hi Lorie,
      Here’s how to do it to make you feel less self-conscious. Just wear those shorts with 1) a cute top that has some interesting detail and 2) perhaps some jewelry by your face, to draw the attention upwards. You husband is right, nobody cares about the scars. Everyone is worrying about themselves.

  15. Great tips! Its so true, I’m 39 and there’s no way I would wear really short shorts. I love dark denim too!

    1. Thanks Jennie,
      I wasn’t out looking for shorts. I don’t wear them much but I saw these and I thought those would look cute on the weekend when I’m by the pool, around the house, having friends over for a BBQ. What I really love is they have a very slight flare which makes them flirty like a skirt. Thank you Banana Republic! Cheers, Deborah

  16. Great tips and picks! I am fortunate to still have toned legs and like to wear a 3″ or 4″ short with flat sandals or wedges.


  17. I too live in a very warm climate. Shorts that are the same length as a skirt you would wear is a good tip. So that’s about on the knee for a straight skirt. As a pear shape, I have also found a straight pair of shorts to be more flattering than tapered shorts and have sometimes resorted to buying pants and shortening them. Capris tend to shorten my legs so I avoid them too.

  18. I just bought long dark wash jean shorts. I am slim, have long legs too – but those shorts look god awful on me. I didn’t realize it until my husband told me I looked like I should be in a bike race.
    Long, snug shorts are not very flattering to anyone I think. I changed into a snug cropped pant and looked so much more in style. I’m done with shorts!

    1. I too was disappointed in the look of snug shorts. A loose top (think gauze, covering the hips) deflects that somewhat, but a straight leg versus skin tight short looks better on me too. Your husband is spot-on: leave the skin tights to the cyclists!

  19. Hi, I am in my early 50’s, have a small, athletic frame, am only 5’4″, and still have a better body than a lot of 20 y/o’s that I see out and about. I have 2 pairs of the long close-fitting jean shorts (as shown above in article) that I wear, but I wouldn’t be caught dead in Bermuda shorts. They look absolutely ridiculous on me. I look downright frumpy. I don’t wear short shorts, but I have found a length that has a medium inseam of 5-1/2 inches. This works perfect for my 5’4″, 31 inseam legs, AND I still look age appropriate! Victoria’s Secret carry some of their shorts in 3 to 4 different inseam lengths. They have some classy looking shorts in their higher end clothes, and I am sure other clothiers do too. Otherwise, I look better in capri leggings and a tunic. I am writing this because I know there are other women of my size and proportions who also look like freaks in those long shorts with wide legs. What do YOU think? AND, a big thanks for all your wonderful, life-saving, confidence-building advice, FOF girls! You rock!

    1. I’m 5’2″ and wouldn’t be caught dead in Bermuda shorts or capris. I have short, runner’s legs. I don’t wear daisy duke length shorts, but a nice 3.5″ rise short looks great on me! I don’t care if people think I shouldn’t wear shorts because my legs aren’t skinny…my legs have been this way my entire life (I’m 46). I can still run, bike, climb, and dot have spider veins or stretch marks. I have some cellulite, but I’m okay with it. Life is too short to let fear dictate how I dress.

  20. I am 60, and ‘probably older than most of the “over 40s” who respond here. I’m proud of my age, still proud of my body but it’s not young or even young-ish. All my life I’ve worked hard to keep myself fit and healthy, exercise, healthy eating etc etc. But there’s no chance that I will wear shorts of any length on the street now. I believe that a good alternative is a sport skirt – As Sophia Loren apparently once said, the calves are the last to go……whether true or not, a sporty skirt with some pocket/yoke/waist detail feels more appropriate to me than shorts. Not “jean blue” but a neutral solid-colour cotton/denim skirt can be very attractive and versatile. I enjoy the Fab 40 site – even though I’m 20 years over that. Thanks for the good ideas!

  21. At 55, I feel like my legs still look pretty good, but I would still never be caught wearing short shorts. When I see a ‘ mature’ woman wearing too short shorts I think it looks very age inappropriate! I don’t think some women see themselves as being mature, but others do..I am always on the lookout for classy looking Bermuda shorts and wish I could find more of them!

    1. I think that anyone is welcome to wear shorts. Short shorts are questionable but really – any shorts are good. Who cares. After 2 battles with cancer and no hair – I think – Who the hell cares and if they do – they aren ‘t your friends anyway.

  22. I almost always agree with you when it comes to your fashion recommendations for over 40 women, but I take a very strong exceiption to the 2 inch above the knee suggestion. This basically means a a bermuda short which is unattractive on women of any age. If women over forty have the legs then they should feel comfortable wearing a 4″ and above inseam – just nothing too short. Bermuda shorts should be banned forever!

    1. Hi Ellen, There are some women in there 40’s and 50’s are still looking good in above the knee shorts or dresses. I don’t beleive in hard “rules”. All suggestions need to be taken as just that… suggested, tips. I hope that everyone that reads this blog take a good look in the mirror and tries to be honest with themselves. That does not mean being too hard on yourself, but being honest. However, your point is well taken. If you have thick legs or knees, longer shorts are recommended. There are ladies out there than can do above the knee but should do so,tastefully (definitely not too short where it’s all hanging out.)

  23. We wear shorts just about year round here in Florida and this year I had better luck at finding some I liked. Several brands came out with ‘bermuda shorts’ this year. They are a bit longer and slimmer. I am so happy to not be in baggy shorts this year! I love these and bought tan, navy and white…oh and a bright shade of blue. I call them my ‘dress shorts’! lol

    1. I have “dress” shorts. Tailored and well made – classic colors so they go with everything. Basic black, navy, and khaki. I can’t keep white – I muar buy a new pair of white every season to keep it looking crisp. AND also “dress” thong-style sandals. It’s a FL thing. A friend of mine quipped “It’s a dressy affair; wear your leather flip flops…”

  24. Glad to see that Fabulous After 40 recognizes that we don’t need to stop wearing shorts after 40. I like mine just above the knee with colorful tops and low wedge sandals or espadrilles.

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