7 Ways to Choose Actually Attractive Shorts

by Julia Friedman

When I was in middle school, I had a favorite pair of shorts. They were made by Soffe, I believe, and they were the color of Pepto-Bismol. On one of the bottom front corners was a screen-printed image of a pair of ballet slippers, and when I rolled the waistband down, the phrase "get the pointe" appeared just a couple of inches below my belly button. I wore them to gym class every day for two years (with a t-shirt that I had cut the neck off of, obviously). But then my waist and hips and the rest of my body began to change and I grew out of those beloved shorts. It felt like the end of an era.

Shorts quickly became my nemesis. They rode up awkwardly against my thighs, made body parts visible that I didn't want to be, and never seemed to fit in a way that flattered my figure.

Even today, I rarely wear shorts, which is kind of a shame because I love my legs! I want to show them off but I just don't really love the way they look in shorts. So instead, I usually stick to sundresses.

But no more! It's time to figure out the formula for finding shorts I actually like.

For some help, I reached out to New York City-based personal stylist and fashion expert Alexandra Suzanne Greenawalt, who agrees that "shorts are as challenging as any other garment and maybe even a bit more because most women carry their weight in the hips area." Lucky for us, Greenawalt, who's releasing her second styling book this fall, has advice for women of all shapes and sizes when it comes to shopping for shorts:

1. Mid-Length Is Middle Ground

If you're in the market for a pair of shorts but aren't sure about the length, a good rule of thumb is to find a style that's somewhere in the middle. "Mid-thigh length shorts are universally flattering," says Greenawalt. Keep this in mind to avoid picking out a pair that's too short or too long.

Styles with a rolled hem allow for a little customization when it comes to where your shorts will hit on your thighs. Just don't roll 'em too much, as this will create a bulky look.

NYDJ 'Briella' Cuffed Shorts, $41, Check Them Out

2. Shorter Shorts For Shorter Gals

If you're petite, and your goal is to give yourself a bit more height, then Greenawalt suggests trying a slightly shorter short. Showing a bit more skin will give the illusion of longer legs — just make sure that your bum is still adequately covered. To elongate your legs ever more, pair short shorts with wedges or heels.

If you're going for short shorts, look for clean hems. This will give your look a bit more polish than a super-frayed pair.

ASOS Petite Tailored Shorts, $30, Check It Out

3. Short And Tight Is Too Much

Short shorts are fine and dandy, but too-tight short shorts are not a good everyday look. It's all about finding a balance that works for your shape and size. "If you've got any cellulite that you want to hide, make sure the shorts are body skimming and not too tight," says Greenawalt. Also good to avoid: tight, lightweight fabrics, which are rarely flattering.

The non-clingy fabric on these shorts offers some movement. Even though they're on the shorter side, they won't also be skin-tight. Plus, a darker wash (like this deep navy color) is usually more flattering than white and other bright colors.

Paperbag Waist Shorts, $26, Check It Out

4. Balance Your Bottom With Your Top

One of the pitfalls of wearing shorts is remembering to balance out your top, too. "Keep your top proportional to your short," Greenawalt reminds us. "Don't wear a long top with short shorts. I see this mistake often." Try pairing Bermudas with a tank or tee instead of a long sleeve shirt. But again, the key is to strike the balance that works for you and makes you feel comfortable.

Alberto E. Rodriguez/Getty Images Entertainment/Getty Images

These short shorts are balanced by a short top, and the cardigan ties the two together. (Image: Getty Images)

5. Be A Low-Rider

If your torso is on the shorter side, then Greenawalt suggests trying low-waisted shorts. This will give the illusion of an elongate mid-section, where high-waisted styles (i.e. shorts that sit above your hips) can make your torso look even shorter.

Shorts that sit right at your hip bones allow more of your torso to show, making it look like you have a longer figure. Wear your shirt tucked in for a little accentuation and to give the illusion of even more length.

Trina Turk Corbin Fitted Tweed Shorts, $228, Check Them Out

6. Or Wear 'Em High

Conversely, "If you have a high waist and short legs you can wear high waisted shorts, which will make your legs look longer," says Greenawalt. It's all about illusion! Focus on the areas that you want to elongate and accentuate and that'll indicate which styles you should go for.

Theo Wargo/Getty Images Entertainment/Getty Images

T-Swift demonstrates how high-waisted shorts can give you legs for days.

Versace High-Waist Orange Shorts, $367, Check It Out

(Image: Getty Images)

7. Side Zips Are Slimming

If you have curvy hips and want a style that's a little slimming, then try a pair of shorts that zips up on the side. Greenawalt feels that this style is the most flattering and won't add any unwanted volume, unlike shorts with bulky front buttons.

A smooth, hardware-less front is slimming. This particular style is great because it offers a little stretch, too, helping to minimize any unwanted muffin tops.

Side Zip High Rise Short, $58, Free People

7. Narrow Hips Can Pull Off Pocket Details

On the other end of the spectrum, women with narrow hips should look for shorts with detailing that'll give your hips more shape (if that's what you're trying to achieve, of course). "Wear shorts with pocket details or pleating," suggests Greenawalt. "Otherwise, steer clear of volume adding details in the hip area as it will make you look bigger."

The pleating on these shorts adds a bit of extra volume, making slim hips look curvier.

Pleat Shorts, $21, Check Them Out