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.

Spanx shorts // LOFT tee // sandals // sunnies // handbag

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.

1. KUT from the Kloth Jane (3 1/2″) // 2. JEN7 Roll Cuff Denim Shorts (4 1/2″ ) // 3. KUT from the Kloth Catherine ( 7″) // 4. similar Bermuda shorts (9″)

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 // AllSaints tee // sandals // earrings

#3. DON’T buy shorts that are too tight (or too big).

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) or just look generally schlumpy. Like most matters of fashion, it’s all about finding that sweet spot. Fit and proportion always matter, but maybe never so much as they do with shorts.

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. 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 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.

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.)

KUT from the Kloth Jane Porkchop Shorts // Sundry Lace Up Sweatshirt // Dolce Vita sandals

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 here is LOW; high heels and shorts are hard to pull off in a classy way. It can be done, but tread lightly… no pun intended. Ha!

I wore the outfit below on vacation in Florida last year, and I think the stripe wrap pulled it together, but I prefer those casual 4″ shorts with flats. I’ll save my wedge sandals for longer, dressier shorts.

7FAM Midroll Short (non-distressed option) // striped wrap // similar tank // wedge sandals

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 (non-distressed option) // old cable sweater // old sandals // 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 // Evereve tank // Marc Fisher slides // tote

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!

Shop Summer Shorts:

Stay In Touch!

If you liked this post, be sure you’re signed up for my email newsletter. In addition to my most recent blog posts, you’ll receive exclusive content like special sales, my newest favorite finds, and an occasional peek behind the scenes — all delivered right to your inbox. Also, I’d love for you to join my Facebook Group!

This post contains affiliate links. When you shop through my links, it helps support my business (at no additional cost to you) so thank you!

Shop the Post
Join the Conversation

25 thoughts on “Dos and Don’ts for Wearing Shorts

  1. How are you finding those Naot Dorith sandals, pictured in one of the pics. I’m still on the hunt for my European adventure this summer. I like the looks of the Naot Sabrina and it is highly recommended but I can’t seem to find them here in Ontario.

  2. I appreciate the review! I haven’t worn shorts outside yet this year. It’s been too cold here in Ohio. But warming up today!

  3. Taking pics and getting that rear view is key! Best advice on shorts and jeans I’ve gotten from your blog! I feel more confident too if I have self tanner on until I get a natural tan throughout the summer! That can also boost confidence:)

  4. Last year I decided to start wearing shorts more and it was because I found I was wearing them too long, hence feeling frumpy. So, now I wear 4-5″ length and feel better and have found some I like to wear. I bought those Jo denim ones you posted here and recommended last Summer and really like them. They are still like new this season. The fit is good too and they don’t stretch out on me. I do still wear dresses too. Great post.

  5. I really appreciate the information you provide. This post is one I’ve referred back to over the last couple of years. A++

    Cheers – Katie

  6. “They are way too wide for my spindly legs.” I have been told my whole like I have skinny legs, even at my highest weight. As silly as it sounds, I couldn’t put my finger on the reason why I didn’t like certain shorts I have. Thank you for sharing.

    1. Isn’t it funny how you get so used to dressing your own body that you don’t even think about why you don’t like something, you just know you don’t? I am the same, I didn’t know why shorts all looked dumpy and too wide on me until I realized I have very wide hips in comparison to my thin legs.

  7. So glad it’s shorts season again! I discovered WHBM’s Pret-A-Play shorts last year and bought two colors. Bought my regular size and they fit perfectly. Sometimes a girl needs something different than denim shorts! I thought they would be too short for my liking, but I’ve grown to love them (thank you self-tanners!). Bought the black this spring (they sold out of black part way through the summer last year and I promised myself I wouldn’t wait this year!) for my trip to Disney and wore all three colors all week along.

  8. I love bermuda shorts. Don’t like to show too much thigh. Luckily I have long enough legs to pull them off.

  9. I’d add to pay attention to the shoe vamp. I think that’s another problem in the pic with the black espadrilles. I agree the shorts are probably a no go either way, but black sandals would chop the leg off less than espadrilles with a high vamp. I’m petite and always have to keep that in mind with shorts. Great post, thanks for the info!

  10. Thanks for this post!! Me being 73, it has opened up my eyes. I tried in shorts at Loft Saturday and have found I can wear them little bit shorter. I was always just above the knee which is an 8 in on me and I did look slumpy. The 4 to 6 in look much better. Thank you again!
    Linda W.

  11. This might seem too “slouchy” a look to suggest lol, but: (particularly, if having top-heavy legs in warmer weather chafe with non-stretchy fabrics) I’d add bike shorts (above the knee length ofc) paired with an oversized tee or sweatshirt as another option.

  12. I’m on the shorter side 5’3″ and I’ve found that a 5-inch inseam is about perfect. Also, if the shorts are looser on my leg, my shirt is more fitted.

    Good post. I hadn’t thought to take photos but I will. Oh,the money I’ll save instead of buying the wrong thing for my body! 😉

  13. Thanks for your advice on choosing the length of shorts to wear. I’m 5’0”, 150 lbs and tend to look frumpy in longer shorts. I’m experimenting with different lengths this summer since the weather’s too hot not to wear shorts! Thanks again for the input!

  14. Thanks for sharing. Agree with the picture-taking to see yourself with a new purchase, mirrors aren’t enough.
    I take videos instead of pictures (running against the timer to see that I wasn’t even frame got old ) the video gives a 3rd person 360 view of yourself in motion and I think it really helps.

  15. Very helpful article–thanks! I’ve been looking for an article addressing shorts. Do you have specific brand recommendations for tall skinny girls? It’s so frustrating only finding shorts with huge leg holes. It makes me so self-concsious that I often shy away from wearing shorts. I had one pair that was pretty much perfect in every respect except thigh size, so I tapered them!

Want More?

Jo-Lynne Shane on Instagram

Click an image below.

Follow @jolynneshane
This error message is only visible to WordPress admins
Error: Access Token is not valid or has expired. Feed will not update.
This error message is only visible to WordPress admins
Error: Access Token is not valid or has expired. Feed will not update.