Dos and Don’ts for Wearing Shorts

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.


Sanctuary shorts // black tank // sunnies // earrings

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.

Tips for Wearing Shorts In Your 40s and Beyond

#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.


1. KUT from the Kloth 3 1/2″ // 2. JEN7 shorts 4 1/2″ // 3. Wit & Wisdom shorts (7″ cuffed // 4. similar Bermuda shorts 9″

Here are a few general guidelines to consider:

  • 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.

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.


Jen7 shorts // black tee // slides

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

I sized down in these shorts a couple years ago, 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. 


WHBM utility shorts // Everlane tee

That said, beware of buying shorts too big, which is the mistake most women our age tend to make. Buying shorts too big 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 4″ Shorts (6″ option) // LOFT muscle tee // sunnies

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 shorts // Sundry sweatshirt

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.


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, 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 // 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.


Banana Republic linen shorts and similar sweater tank // Tory Burch Miller Sandals

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 shorts // Evereve tank // Marc Fisher slides // tote

In Conclusion

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.

Also, a little self tanner goes a long way. There’s also a lot of good leg makeup available these days, if you care to go to the trouble of applying that.

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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