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How To Confidently Wear Shorts Over 40, 50

Not all midlife 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 over 40 or 50 and feel good about it.

shorts over 40 tan with animal print tee Deborah Boland

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1. Choose a Flattering Length

How short is too short when you’re middle-aged or more? Determining the best length is always tricky, but it boils down to your figure, where you plan to wear your shorts and your confidence level. There are basic lengths:

  • Short Shorts are most flattering on toned legs. Aim for short shorts with an inseam minimum of 4″ -5″. Anything faster will look skimpy and unflattering on a grown-up gal.
  • Medium Length Shorts are popular with women 40,50+. Medium-length shorts have a 5-10″ inseam and are several inches above the knee.
  • Long Shorts: Classic Bermuda shorts end at the top of the knee AND are a great choice if your legs are not as firm as they used to be or you need a pair of more formal shorts. Bermuda shorts usually have an inseam of about 11 inches.

Tip: Try this trick if you’re still unsure about what length to wear. While standing up, 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.

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2. Consider Sizing Up

To fit right, shorts shouldn’t be tight in the thighs, bum, and crotch. If the shorts have side pockets, they should lie flat, not flare out at the hips. Sometimes, it helps to go up one size in shorts, especially with white shorts, which tend to show everything.

As for the leg opening size, if it is too wide, your legs will look skinny, and the shorts will look baggy, giving you a frumpy look. If the leg opening is too snug, you will look squished into those shorts, which look desperate. Experiment to find that middle ground.

 

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3. Wear Tailored Shorts

Wear shorts with structure if you want to look more sophisticated. Shorts that are slightly more tailored and less flimsy will help give your softer, rounder 40+ body an excellent shape and make you look more polished and chic. For example, flat-front walking and Bermuda shorts are more tailored and trending. Even a pair of crisp paper bag waist pants can have a more polished look.

4. Don’t Wear Skimpy Tops with Your Shorts

You want to look classy, not trashy! If you reveal many legs, cover up more above the waist. A skimpy or very fitted top worn with short shorts looks tacky after a certain age. Balance your look.

 

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5. Create a Style Theme

A mish-mash look doesn’t help you look chic in shorts. Try to coordinate the colors and the mood of your shorts outfit, or pick a theme to build on to look pulled together. For example, give your outfit a natural woven vibe by wearing this linen, straw, rope shorts outfit above. More great shorts-style themes here.

 

 

Shorts over 50 black bermuda shorts

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6. Layer the Third Piece

Never underestimate the power of the third piece to dress up anything, including shorts. I like to wear long black shorts with a bright linen jacket. You can also wear a denim jacket, cardigan, or third layering piece to add polish and maturity.

 

7. Wear Flats or Low Heels

Flats are perfect with shorts. A low to medium wedge or block heel is about as high as you want to go without looking like you’re in a beauty pageant.

 

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8. Add Classy Accessories to Dress-Up Shorts

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

 

9. Uplevel Shorts with Good Grooming

Well-groomed hair and some makeup help dress up shorts and take you from average to excellent.

 

 

blue-jean-shorts-over-40

 

10. Swear Off Daisy Dukes

Cut-off jeans shorts with frayed hems are just too short and junior for a mature woman. Don’t even go there. The best denim shorts for women are

          • Dark wash denim- dressier and more slimming.
          • Chambray is modern but looks more relaxed.
          • Jean shorts with no or minimum rips or whiskering

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.

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71 thoughts on “How To Confidently Wear Shorts Over 40, 50

  1. I like these tips for wearing shorts after a certain age. I must confess, though, that I still love my cutoffs, and I’m 65 years old! They are not Daisy Dukes, though. They have a long inseam, and I mainly wear them around the house.

  2. Deb, I liked your tips on shorts, you were very helpful. In case anyone missed the point it was how to look classy wearing shorts! Last year I donated any with an inseam less than 6” and purchased some nicer matching tops, and yes, the self-tanner disguises spider veins, etc. save flip flops for your patio and wear some fab comfy sandals in a pretty color too! I enjoy your style advice!!

  3. Love the shorts outfits! The gold sneakers shoes in your introductory picture…what would the brand be?
    Thank you!

  4. Hi Deborah,

    Great article about shorts, you look fab and stylish.
    Shorts in the winter with opaque tights over 40? Would you say yay or nay? If yay, how to style it?
    Thank you

  5. 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 offended. lol! 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 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

  6. 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 thirty, 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.

  7. 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 them, I look at them, talk like them, and social media like them, but turning 40 last year didn’t seem to register in 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 WAY. 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

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

  9. 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 a 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.

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

  11. 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 the 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!

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

  13. 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 women 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!

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

  15. 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?..by whose standards? I’m sure you look beautiful and can rock whatever you want to wear.

  16. 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… The casual state overall for everyday dress; even the police wear shorts, so if the police can wear summertime shorts, so can we!!

  17. “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.

  18. 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 on your face, to draw the attention upwards. Your husband is right, nobody cares about the scars. Everyone is worried about themselves.

  19. 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, or 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

  20. 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.

    Jill
    dousedinpink.blogspot.com

  21. 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.

  22. I just bought long dark wash jean shorts. I am slim, and 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 pants 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!

  23. 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 the 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 perfectly for my 5’4″, 31 inseam legs, AND I still look age-appropriate! Victoria’s Secret carries 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 has 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.

  24. 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. 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 sports 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-color 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!

  25. 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.

  26. I almost always agree with you when it comes to your fashion recommendations for over 40 women, but I take a very strong exception to the 2-inch above-the-knee suggestion. This basically means a Bermuda short which is unattractive to 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 their 40’s and ’50s who are still looking good in above-the-knee shorts or dresses. I don’t believe in hard “rules”. All suggestions need to be taken as just that… suggested, tips. I hope that everyone that reads this blog takes 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 who can do above the knee but should do so, tastefully (definitely not too short where it’s all hanging out.)

  27. 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 must buy a new pair of white every season to keep them looking crisp. AND also “dress” thong-style sandals. It’s an FL thing. A friend of mine quipped “It’s a dressy affair; wear your leather flip-flops…”

  28. 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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