Dos and Don’ts for Wearing Shorts

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.

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.

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. It’s fine to wear different lengths, but most of us look better in some lengths than others.

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.

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″ // 4. Paige Jax 9″ cuffed

I did a poll in my Facebook Group to see what length of shorts most women over 40 prefer (assuming most in our group are over 40) and mid-length shorts (5-7″ inseam) was by far and away the most popular vote.

As for me, I have a variety of lengths in my closet, and I take into account the venue and social situation when choosing which shorts to wear. My favorite length is a 4″ or 5″ inseam, but I’ll go shorter around the house or at the beach, and sometimes I want a longer length for dining out or church events.

#2. DON’T ignore the rear view.

Just like with jeans, the rear view can make or break a pair of shorts. Pay attention to pocket placement, and make sure the shorts don’t sag, nor do you want them to pull across the rear.

Joe’s Jeans Frayed Denim Shorts (28) // AllSaints tee (S) // sandals (8) // earrings

#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 unfortunate places… ifyouknowwhatImean. 

Tips for Wearing Shorts Over 40: Don't buy shorts that are too tight.WHBM utility shorts // Everlane 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.  

As we get older, quality matters, 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.

Spanx Stretch Twill Shorts 4″ (6″ option) // LOFT muscle tee // sunnies // necklace // bracelet

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 where I wear them.

#5. DO pay attention to the leg opening.

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.)

Wit & Wisdom shorts (6) // LOFT muscle tee (S) // earrings // necklaces one & two // bracelet

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 when I compare pictures, rather than just looking at myself in the mirror.

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. In the pictures below, the ones on the left are okay, but the ones on the right are a big, fat NO. They are way too wide for my spindly legs.

shorts comparison

Also, 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.

To visually elongate your legs when wearing shorts, especially longer shorts, wear shoes with a low heel. The key word is LOW heel; high heels and shorts are hard to pull off in a classy way. It can be done, but tread lightly… no pun intended. Ha!

7FAM Midroll Short Destroy (28) // striped wrap // rib tank (M/L) // wedge sandals (8)

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. Also, shoes with less foot coverage will help with the appearance of longer legs.

7FAM Midroll Short Destroy (28) // 525 cable sweater (S) // Dolce Vita studded slides (8) // earrings // sunnies // tote

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.

Sanctuary Switchback Rolled Shorts (28) // Evereve tank (S) // Marc Fisher slides (8)

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 on the higher end of the age 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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23 thoughts on “Dos and Don’ts for Wearing Shorts

  1. Thanks for this post, very helpful, just a tip I have recently learned, Sally Hansens, airbrush legs is wonderful, it hides a lot of imperfections, veins, age spots, etc and you just spray it on and rub it in, leave it 60 seconds to dry and it’s a game changer for me, gives you a tan and covers a lot, dries quickly and does not rub off even on white! Try it….

  2. Jo-Lynne…what do you recommend as a length when you’re short (5″1) but carry your weight in your thighs…is it better to still do a “mid-length” or is a longer length more flattering when you don’t have skinny legs?

  3. I am absolutely going to try this product. I’ve had very ugly veins on my legs for years, and have had surgery to try and correct them which helped a little. I have nice legs other than the veins and am very excited to see what this product can do for me. Thanks for the tip!

  4. You mentioned “frayed hems”… How do you deal with the “on-going” fray? Every time I wash a pair of denim shorts, the hem gets more frayed and messy…Is there a trick to stopping the fray from getting worse??


  5. Help! How do you deal with ‘frayed hems”? Every time I wash my denim shorts, the frayed hem gets messier and more frayed! Is there a trick to keeping the fray looking tidy and to stop it from continuing to fray?


    1. The first few washes the fray will get worse, and you can trim the long strands. But in every pair of cutoff or frayed shorts that I’ve purchased, there is a line of stitching so that the fray wont continue all the way up the shorts. So there is a stopping point, but it definitely gets crazy the first few washes. Then after that you don’t have to trim them much, if at all, anymore.

  6. I quit wearing shorts for a long time, but I have to say with my daughter’s encouragement and your posts on how to wear them and what to look for, I finally have some shorts I really like and will actually wear out in public. Lol. Finding the right length was key along with deciding my 65 year old legs are what they are. Your “final word” on shorts is on point!

  7. Always a great post– some of us need reminding of these rules. I have long legs, so even though I’m 60 and a size 10/12, I prefer shorter lengths. 5inches seems perfect for me most of the time, but I have a fav pair of 4 inch that I’ll wear until they fall off me and I also have a couple of pairs of longer shorts. And I so appreciate your reminder about being kind to ourselves, Jo-Lynne! I have to remind myself that I would never judge someone else’s appearance the way I judge my own.

  8. Thanks for this post. I learned a lot from your Illustrative photos showing do’s and don’ts. Great take-away regarding skin tone shoes and leg length appearance. I’m guilty of wearing dark, longer shorts with dark shoes…no more. Hope you’re continuing to feel good as you recover.

  9. You look so cute! I miss wearing shorts, San Francisco is too ding dang cold most of the time, I just stopped even trying to buy any. The hubs bought me a pair years ago, I wore them ONCE in Las Vegas 10 years ago. They went to the Good Will.

  10. Best advice so far about wearing shorts. I’ll probably have to scroll through many more pages to find some practical advice such as yours. Thank you.

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