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 Fight the Frump post with some dos and don’ts for wearing shorts over 40… or at any age, really. But it does seem like women over 40 struggle with them the more than younger women do.

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

I’m not one to set an arbitrary age at which to stop wearing a certain wardrobe piece. I believe the question of wearing shorts over 40 is like any other trend or article of clothing: it’s way more about personal style and practical factors than age.

Another comment I often get when discussing shorts is, “My legs are too fat/thick/old/pale/veiny {fill-in-the-blank} to wear shorts.”

I say it’s all about your personal comfort level. No one else 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. It’s more important that you wear shorts that fit properly and are appropriate for the occasion. Beyond that, it doesn’t really matter what your legs look like. Also, a little self tanner goes a long way!

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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, I can definitely share some of my personal dos and don’ts for looking your best.

Dos and Don’ts for Shorts

#1. DO find your ideal inseam length.

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″ Stretch Shorts

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) are pretty much universally flattering.

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

I’m 5’5″, and I 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.

wearing: Old Navy 3.5″ Pixie Shorts

One of my best tips when shopping for shorts is to pay attention to the size of 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.)

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?

#3. DON’T ignore the rear view.

wearing: White House Black Market 5″ Stretch Shorts

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!!!

I take pictures of myself from behind so I can get an accurate idea of what my shorts and pants look like. Needless to say, the ones above went back.

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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.

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

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

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 a 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!

#5. DO buy quality shorts.  

wearing: Ann Taylor City Shorts

As we get older, quality matters more and more — and that is especially true with shorts. 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 wisely when and where to wear them.

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