Dos and Don’ts for Wearing Shorts Over 40

This time of year, I get so many questions about shorts! Shorts can go really wrong when they don’t fit well, so I wrote a post with some dos and don’ts for wearing shorts over 40… or at any age, really.

Shorts can go really wrong when they don’t fit well so, so here are my dos and don'ts for wearing shorts over 40 and looking your best.

Of course, if you aren’t comfortable wearing shorts, you certainly don’t have to. There are lots of other options out there (see my post, Casual Alternatives to Shorts for some ideas), but if you are going to wear shorts, I put together some tips for looking your best. Also, a little self tanner goes a long way!

Dos and Don’ts for Shorts

#1. DO find your ideal inseam length.

Tips for Wearing Shorts Over 40: Know your ideal inseam length.1. J.Crew 3″ cuffed // 2. Joe’s Ozzie 4″ // 3. KUT from the Kloth 7″ cuffed // 4. Paige Jax 9″ cuffed

Your ideal inseam length will probably be a range, not an exact measurement, and it depends on your height and body type as well as your personal comfort level.

As a rule, petite ladies tend to look better in shorter shorts because showing a bit more skin will give the illusion of longer legs. If you’re taller than average, you’re more likely to be able to pull off Bermuda shorts, which tend to look frumpy on the rest of us.

Mid-length shorts (around finger-tip length) are pretty much universally flattering, and any woman can wear them. It’s fine to have some of each, but most of us look better in some lengths than others.

I have a variety, and I take into account the venue and social situation when choosing what length of shorts to wear.

#2. DON’T ignore the rear view.

Tips for Wearing Shorts: Pay attention to the rear view! Kut from the Kloth Gidget Raw Hem Shorts // Boden t-shirt (old)

Just like with jeans, the rear view can make or break a pair of shorts. In my denim shorts review (coming soon!) you will see what I mean. Some shorts look great from the front and sides, but when I turn around, yowsah!!!

YOU MIGHT ALSO LIKE: Fight the Frump: Denim Mistakes You Might Be Making & How To Fix Them

Pay attention to pocket placement, and make sure the shorts don’t sag, nor do you want them to pull across the rear. Clearly these went back.

Summer Shorts Review: GAP Mid Rise 5" Denim Shorts with Raw Hem in Saltwearing: GAP Mid Rise 5″ Denim Shorts with Raw Hem #justsayno

#3. DON’T buy shorts that are too tight.

I sized down in these shorts last summer, and I regretted it all season long. When shorts are at all snug through the hips and bum, they will make the side pockets flare out, and they can ride up in… um… unfortunate places. 

Tips for Wearing Shorts Over 40: Don't buy shorts that are too tight.wearing: WHBM Utility Shorts // Everlane The Pima Micro Rib Cap-Sleeve Tee

Of course, sizing up in shorts can create an issue with the leg opening (see #5.) Like most matters of fashion, it’s all about finding that sweet spot.

I always recommend trying several sizes, and if you’re unsure, wear them around the house for a few hours before taking off the tags. Be sure to sit down, bend over, and move around to make sure they will be comfortable to wear in all situations.

#4. DO buy quality shorts.  

Tips for Wearing Shorts Over 40: Quality matters. Caslon Cotton Twill Shorts // Treasure & Bond striped sweater

As we get older, quality matters more and more — and this is especially true when wearing shorts over 40. Keep it classy with good quality shorts in classic styles, and pair them with dressier tops when you want a more sophisticated look.

Frayed hems and distressing are very on trend right now, but they’re definitely a younger look and may not be appropriate for all situations. I actually love them, but as I get older, I’m more selective about when and where I wear them.

#5. DO pay attention to the leg opening.

Shopping Tips for Summer Shorts: Pay attention to the inseam length. Caslon rolled boyfriend shorts // Caslon French terry hoodie // BP. sandals

Ideally you want your shorts to follow the line of the leg without being too tight. If they’re too wide, you’ll look frumpy, but you also don’t want them to be too tight through the hips and rear (check both the front and back views.)

The best way to determine your ideal pair of shorts is take pictures of yourself in the mirror, and compare. For some reason, I can get a lot more clarity about what works and what doesn’t style-wise when I compare pictures, rather than just looking at myself in the mirror.

Also, try to stand the same way every time, and don’t necessarily stand at your most flattering angle. Stand straight on and see what you “really” look like.

shorts comparison1. Gap 3″ Mid Rise Khaki Shorts // 2. Loft 4″ Washed Twill Shorts

The style and color of your shoes will also affect which length of shorts looks best. In the above pictures, see how the neutral shoe combined with a shorter short creates a longer, leaner leg line; whereas the black espadrilles (while very cute!) with the longer shorts visually shortens the leg.

And that is the perfect segue…

#6. DO wear a low heel or shoes that are close to your skin color.

Tips for Wearing Shorts Over 40: With longer shorts, wear a heel or shoes with low contrast to your skin tone.Paige Jax Bermuda Shorts // Everlane The Pima Micro Rib Cap-Sleeve Tee // old wedge sandals

To visually elongate your legs when wearing shorts over 40, especially longer shorts, wear shoes with a wedge or low heel.  If you don’t want to wear heels, a shoe in a neutral shade with a low contrast to your skin tone will look best.

In the next picture, you can see how wearing black shorts and black sandals visually shorten the leg line. I still like this outfit, but I have long limbs, so I can get away with bending this rule a bit. It also works because these shorts have a shorter (4″) inseam. But if you feel like shorts make your legs look stubby, you will generally look best in a neutral shoe that is close to your skin tone.

Tips for Wearing Shorts Joe’s Jeans 4″ Ozzie Denim Shorts // Free People Camo Clare Tee // Marc Fisher Pava Slides // Gypsy Creations Hoops

A final word on the topic of shorts: Whenever the subject of shorts come up, I hear women bemoan the condition of their legs, especially those of us who are on the older end of the spectrum. Every body is different, and we all have things about ours that we don’t like, but let’s be kind to ourselves.

What’s important is that you wear shorts that fit well and are appropriate for the occasion. Beyond that, it doesn’t really matter how old you are or what your legs look like. And always remember, no one pays nearly as much attention to your perceived imperfections as you do. That is the mantra I speak to myself when I’m feeling self-conscious about something.

Of course, you don’t have to wear shorts of you don’t want to, but if you do, I hope this post is helpful!

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37 thoughts on “Dos and Don’ts for Wearing Shorts Over 40

  1. I am 5’4 and a runner. My legs are not stick thin and never have been. My legs aren’t super muscular, but they are shapely. Thank you for clarifying who can wear Bermuda Shorts. I’ve been debating on buying a pair. They look AWFUL on me. I do like to wear a short short–like the 3 inch inseam. I can pull it off, but wondering if I should start wearing a 5 inch. I have a 5 inch pair of ‘girlfriend’ khaki shorts that I like to wear. I bought an athletic skort to wear also-haha.

    Great and honest article! Thank you.

    1. Kathleen: I am 5 foot and have toned legs and I, like yourself, look awful in a bermuda short I wear a 3 inch and feel very confident in them and they look good. I am 59 years old. So wear what you feel confident in and what looks good. Show off those legs!

  2. I am one of your followers that does not feel good in shorts that are not close to the Bermuda length, for lots of reasons. I have finally woken up and realized that since I don’t feel good about my appearance in shorts, I am better off wearing other bottoms so that my confidence level will be better. The overall fit of the shorts is so important. I do have a few pair of shorts that I wear, and when I do, I put extra thought in what top, shoes, jewelry, etc., I pair with them. You’re right, we are much too critical of ourselves! I hope you have a great day!

  3. I love shorts and have always worn them. I’m short-waisted, 5’7″, and a 10/12 with very muscular legs. I bought a pair of Bermuda shorts 2 or 3 years ago and culled them this spring because I liked the idea of them, but I didn’t like them on me. I must have taken them out of my drawer, tried them on, and put them back dozens of times each summer. I love a 4 inch short but 5 works, too. I do have some veins on my legs (I’m 59) but I found that self-tanner covers them well enough that I’m not self-conscious. I agree with Jo-Lynne that we need to wear what we’re comfortable in, and what makes us feel good about ourselves. I don’t think we have to worry about what’s age-appropriate. I still wear my hair in braids when I hike, sometimes!

    1. Hi Colleen! I’m 5’8” and find Bermuda shorts look good on me. They are just a little dressier, I find. I think it’s all about the proportions of your top. I’m not short waisted so perhaps, JoLynne can give you some direction on how to make them work for your body type.

    2. I do agree that Bermuda shorts look best on thinner legs, or super long legs. I like my white pair with a heel for a more elevated look, but I don’t find myself wearing them much.

  4. Love this shorts post! I’m 5’7″ with long, thin-ish legs so I like wearing shorts (all my extra weight in in my tummy area!!), and I really love the bermuda shorts! As long as they are lean, and not reaching the top of knees, I think they are flattering on me. (and they also hide veins on the back of the legs!!) Funny story, I wore a nice pair of lean tan-colored bermudas to a local garden where lots of photos were being taken. Looking back on the photos, it always looked like I was wearing NO pants, since the shorts were so close to my natural skin tone! My family got a real kick out of it and I’m always teased about it! Lesson learned! HAHA!!

  5. Hi Jo-Lynne, I love your blog! I’ve learned so much from you and I’m always Inspired by your great style.
    I’m curious of your take on the paper bag shorts? I was looking at a cute pair of Caslon paperbag shorts at Nordstrom site. I love that look but at 5’2 I’m just not sure that’s the best look for me. Any thoughts on that style?

  6. I just ordered the Caslon rolled boyfriend shorts to try. I LOVE the way they look on you! I’m not super hopeful though because I have thicker legs than you and a cuff can add bulk. But they’re so cute!🤞

  7. Great post!
    At some point my mom refused to wear shorts because of sun damage (and she had great legs!) I told her no one was looking at her legs, but she never wore shorts again. My legs, in my opinion, are my best feature (even with sun damage – oh, why didn’t I use sunscreen when I was younger?), and I love wearing shorts. I don’t like how Bermuda shorts look on me (I am 5’5″, very high waisted), but I find that 4-5″ shorts are best for me. I cannot wait to be able to have a longer short season in North Carolina. Three more weeks!

  8. I love this post it answers so many of my questions! I never considered that I’m short waisted and that changes the look of my shorts. This is so helpful!

  9. I have not worn many shorts in the last few years, but last year during lockdown I gave up and wore the few pair I had stashed away from our past Hawaii trips, thinking I wouldn’t be out in public much. I discovered they are more comfortable than capris in the really hot weather. Ha! My daughter convinced me to get some shorter ones this year, because all I have are bermuda. I wasn’t sure this 64 year old could do it, but after reading a few of your blogs on the various inseams, I finally broke down recently and bought some 7″ and I really like them. I have very short legs, so the shorter inseam does help make them look longer. Thank you to you, Jolynne, and my daughter for a bit of a push. Ha Ha.

    1. That’s awesome! 7″ is a nice length, still very “respectable” but should definitely help elongate the leg a bit over bermudas.

  10. For some reason three things happened to my legs. The first was a roadmap of spider veins especially behind the knee. The second was the development of brown spots and scars from Grovers disease. And the final straw was something called strawberry skin. I asked my dermatologist about the red bumps and she she said with a laugh, wear long pants because none of the old wives tales remedies will work. And reminded me that at 70 I’m entitled to retire my shorts. I kept one pair of Bermuda length to wear when I wash the car and they are fine for that. I tried looser medium length ones but for some odd reason, they ride up between the thighs where the upper leg narrows. So I’ll just have to remember fondly my 110 lb 18 yr old self in daisy dukes so short that the pockets hung down below the ragged edge. Sneaking them past my dad was such a challenge! My hubby said I’ve managed to live to 70 and I’m completely healthy, no medical condition other than allergies, and I don’t look a day over 50. Thanks to fillers and Botox and excellent nutrition. So I just hide them under crops that end just below the knee.

  11. Shorts really are hard to find for me. The older I get the more I want to wear casual dresses. Great informative post.

    1. I wish I liked dresses better. They definitely look more elevated than shorts. I always feel too breezy under there… lol! I feel so much more comfortable in shorts or pants.

  12. Shorts. Always a hard find for me. I’m getting more dresses these days. You and Cyndi both did a shorts post today.

  13. I love this post! As I was pulling out my shorts to put them into rotation for warmer weather, I was beginning to question if short shorts were appropriate for me (45 years old). Thank you for passing along some encouraging words to wear shorts if we love them & think we look good. And for the hot tip about paper bag shorts (in the comments). Those bows look so cute but I never thought about the ideal top to show off that cute bow!

  14. I think if you have decent legs by all means wear shorts. I am 62 years old and have lily white legs and have developed really bad cellulite so I don’t wear shorts but would love to. I am 5’4″ and 125.

  15. Thanks for the timely shorts “how to”s. The reminder about wearing nude/ tan colored sandals to lengthen the leg length line is so true! I have been self conscious about some veins in my legs but then smiled when you wrote no one else cares or bothers or notices and they are probably self conscious about something they have! I love the black t-shirt with white shorts look. You have inspired me to pull out my white shorts for when its warmer out.

  16. Love this! Very helpful as usual. I love wearing shorts and at age 50 I can admit that it’s the one part of my body I still feel fairly confident about. However, I’e noticed that I now feel much more comfortable & stylish if I pair them with a long sleeved top, tucked in, usually a button down. For some reason it elevates the look so much more than when worn with tees. I also love a slide rather than a flip flop for the same reason!

  17. By the way, I forgot to mention that I am 51 years old. I love and like to wear shorts 24/7 and I do

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