Fight the Frump: Dos and Don’ts for Shorts

I get so many questions about shorts for women over 40 that I decided to write a Fight the Frump post about it! Shorts can go really wrong when they don’t fit well so it’s definitely a topic worth discussing.

Dos and Don'ts for Wearing Shorts for Women Over 40 | I get so many questions about shorts for women over 40 that I decided to write a Fight the Frump post about it! Shorts can go really wrong when they don’t fit well so it's definitely a topic worth discussing. I realize some women prefer not to wear shorts, and that's okay; there are plenty of other options! But if you wear shorts, here are some dos and don'ts for looking your best.

One question I get a lot is, “Is there an age at which a woman is too old to wear shorts in public?”

Another comment I often get when discussing shorts is, “My legs are too fat/thick/old/pale/veiny to wear shorts.”

First off, I’m not one to set an arbitrary age at which to stop wearing a certain trend or type of clothing. I believe it’s more about personal style and practical factors than age.

And as far as women not liking how their legs look… that’s a personal decision, but if you find shorts that fit properly and look nice on you, I wouldn’t let that stop me. Also, a little self tanner goes a long way!

Ultimately, I think these are questions every woman has to decide for herself based on a variety factors including climate, venue, personal style, and general comfort level, but if you are going to wear shorts, there are definitely some dos and don’ts for looking your best.

Dos and Don’ts for Shorts

Dos and Don'ts for Wearing Shorts for Women Over 40: Find your ideal inseam length and more shorts advice!

wearing: White House Black Market 5″ Coastal Stretch Shorts

#1. DO find your ideal inseam length.

Determine the inseam length that is right for you. This is usually a range, not an exact measurement. Typically shorts are short (3½” – 4″ inseam), mid-length (5″-7″) or Bermuda (9″-11″). Most women look best in mid-length shorts.

(I think it goes without saying, but shorts that are short enough for the pockets to be hanging out or to show your undergarments are too short — at ANY age. #justsaynotobootieshorts)

Petite girls 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 (or finger-tip length) is pretty much universally flattering.

wearing: Joe’s Jeans 3 1/2″ Rolled Hem Denim Shorts (similar)

I’m 5’5″, and I actually prefer a 3½” or 4″ inseam on my shorts, but I don’t mind 5″ or 6″ if I wear them with shoes that are neutral and/or have a low vamp. (The higher the vamp on your shoe, the shorter your leg will look, so sometimes you have to compensate by shortening your shorts or skirt.)

STYLE TIP: To elongate your legs, pair short shorts with wedges or heels.

The best way to determine your ideal inseam length is to try on various lengths, 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.

wearing: Gap Mid Rise 3″ City Shorts & Loft 4″ Riviera Shorts

The style of shoe you’re wearing and the style and length of your top will also help dictate what length of shorts looks best. In the above pictures, see how the neutral shoe combined with a shorter short elongates the line of the leg and makes them look longer, whereas the black espadrilles (while very cute!) with the longer shorts visually shorten the leg. The longer shorts are also too wide, which is the perfect segue…

#2. DO pay attention to the leg opening.

One of my best tips when shopping for shorts is to 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 an back views.)

I have wide hips compared to my thin legs, so I have a hard time finding shorts that fit the hips but aren’t too wide in the legs — especially with chino shorts. I’m thinking of taking a pair to a tailor to see if they can take them in on the side seams. Has anyone ever tried that?

wearing: Old Navy 3 1/2″ Pixie Shorts

#3. DON’T ignore the rear view.

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 in the rear, nor do you want them to pull across the rear.

wearing: White House Black Market 5″ Coastal Stretch Shorts

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

I usually have to size up in shorts to get a comfortable fit. I wear a size 6 in most pants and jeans, but I often wear an size 8 in shorts. When they’re at all snug through the hips and bum, they will make the side pockets flare out, and they can ride up in… um… unfortunately places.

I’m usually more comfortable when I size up in shorts, but that doesn’t help the leg opening issue I have (see #2.) Like most matters of fashion, it’s all about finding that sweet spot!

wearing: Kut from the Kloth Gidget Denim Shorts, similar .

#5. DO buy quality shorts.  

As we get older, quality matters more and more. Keep it classy with good quality shorts in classic styles, and pair them with dressier tops when you want a more upscale look.

Frayed hems and distressing are a more youthful look. I’m not going to say to never wear them (y’all know I love ’em!) But know your audience, and choose when and where to wear them wisely.

Dos and Don'ts for Wearing Shorts for Women Over 40

wearing: AG The Hailey 3 1/2″ Cuffed Denim Shorts

Is this post helpful? What would you add to my advice?

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