How to Wear Shorts

I hate to brag, but I have legs for miles. Except that I’m 5’2″. So I guess it’s actually inches. I have legs for inches.

Seriously, with a short waist and longish legs, shorts have always been my friend. Add to this the fact that I live in Florida and my legs (unlike my face) haven’t changed much since high school, and you can see why shorts are a summertime staple for me.

But shorts are not for everyone. And that’s totally fine. I have had so many women tell me that they are uncomfortable with the way they look in shorts. My answer? Then don’t wear them. There is absolutely no reason to wear something unflattering or that makes you feel less than lovely. None.

It pretty much comes down to this question: How do I feel about my legs? If you like them, or are relatively comfortable with them, then you can find a pair of shorts to fit and flatter. If you don’t, then skip the shorts. There are countless alternatives. Cute, comfortable culottes, maxi skirts and midi skirts might be more flattering choices, and they’re just as practical and comfortable.

If you are ready for shorts, you’ll want to find just the right pair. Fortunately, I can help! Here, how to wear shorts, in 71 simple steps.

Length Matters

Before we dive into flattery, and finding the right fit and style for your body type, let’s talk length for a minute. The length of your shorts is critical to how flattering they are, and fortunately, many brands, from Old Navy to J. Crew, have caught on, and are selling shorts by the length of the inseam. The key with shorts, and skirts, and virtually anything else, is to avoid drawing a line at an unflattering part of your body. If you’re not fond of your knees, then don’t choose a pair of shorts with a hem that hits directly at or above the knee, or you will, in effect, be pointing an arrow at them. The hem of your shorts is a detail that attracts the eye, so make sure it is at a flattering place.

Sometimes, it helps to have a starting point. If you already own a pair of shorts that you love, or a pair that you loathe, try them on and try to determine why they flatter — or don’t. Measure the inseam, and make note of the details. This will inform your future shorts-buying decisions.

(Note: As always, just click on the picture to shop, and Amazon links are affiliate links.)

Cool Resource:

Search by Inseam is a fabulous site developed by a frustrated tall woman who was unable to find pants. It allows you to search for styles by inseam length, so that you can find a great fitting pair of jeans, shorts or pants.

Here, some more hints for finding the right length for you!

Shorts for Petites

Most stylish mamas steer clear of short-shorts, but if you’re petite, shorter shorts can do a great job of lengthening your leg! Look for a length of 3 1/2-5″, which lengthens the leg while still covering the inner thigh. Avoid horizontal stripes (unless they’re skinny stripes) and huge prints. If you’re petite with long slim legs, cuffed and rolled up styles can work, but other petite women should avoid them, as they tend to make legs appear shorter. If you have a long waist/torso, try the leg-lengthening effect of high-waisted shorts. Petite and plus? Go for a mid-length short (7-8″ inseam) in a thicker fabric with a side zipper. Heels and wedges can also help you appear longer; just make sure to balance out shorter shorts with a relatively modest top. And make sure the top hits at your waist or just below it. Short shorts and a long top are a sloppy combination.

LOFT petite lace shorts feature a pretty all over lace and a 4″ inseam, $54.99, LoftOnline.com

Shorts for Plus Sizes

Bermuda shorts are the most flattering length for most plus-sized women, except those who are petite and plus, who should go for mid-length shorts. Bermuda shorts are usually anywhere from 8-10″ in the inseam. Their downside? They can make your legs look shorter. Just make sure they don’t hit below your kneecap, and go for a slightly shorter inseam if you feel that the shorts take too much away from your height. Look for a thicker, durable fabric that will hold up well all day and won’t show lumps or bumps. Heels or wedges can also counteract the shortening effect of Bermudas.

Lucky Brand jeans “Ginger” Bermuda shorts, $41.70, Amazon

Shorts for Tall Girls

If you’re tall, with slim legs, the always flattering mid-length shorts, with about a 7-8″ inseam, will be super flattering, although you can pretty much wear any length, from short shorts to Bermudas. To maintain the balance of long legs in shorter shorts, break up the eye with cuffs or a roll-up style.

Silver Suki mid Bermuda shorts, $59, LongTallSally.com

Shorts for Everyone

Walking shorts, sometimes called classic shorts, are mid-length and universally flattering, with an inseam of about 7-8″.  These are short enough to lengthen the body yet long enough to provide thigh coverage, and they can be dressed up easily with a pair of heels and a silky top.

Old Navy stretch twill shorts with 7″ inseam, $22, Old Navy

The Right Shorts for Your Body Type

If we’re really going to be friends, you’ve got to let me help you out. And no, I don’t mean watching the kids while you nap or anything, although I’m always up for cuddling with some littles. Let me help you discover your Body Type! I promise — it only hurts for a second. When I first started training with The Stylist Online, the concept of body types seemed limiting to me. I felt like I would be given a long list of what-not-to-wears. What I learned, however, is that it’s actually the opposite. A true understanding of your unique body shape opens up your options and gives you ideas for can’t-miss silhouettes and styles that flatter you every single time. After I do a Virtual Style Dial® Analysis and tell you your Style Dial® number (i.e. your body type), you can use the Shopping Cheat Sheet to buy clothes with confidence. Focusing on the most flattering options helps you avoid feeling overwhelmed, and prevents you from making expensive mistakes!

Need a little hand-holding through the process? Connect with me on chat when I’m online, or shoot me an email to advice@nadamanley.com! After all, that’s what friends are for.

Once you discover whether you’re a Proportional Hourglass (Style Dial® 1), a Curvy Hipped Goddess (Style Dial® 2) or a Straight Up Supermodel (Style Dial® 3), it will be easy to choose the right shorts to fit and flatter your body type! Here, the best shorts for each body type, and why they work!

Shorts for a Proportional Style Dial® 1

The key with flattering this proportional body type is to keep the shapes of the clothes simple so that you don’t throw off its natural balance. Shorts should have a sleek simple shape, with streamlined pockets and a mid-width leg opening. You can pull off prints, but avoid extra structure or embellishments on the hips. Cuffs are okay but not preferable.

Zig Zag Ikat shorts, $69.50, J. Crew

Joie “Catia” linen short, $148, Amazon

Rebecca Minkoff “Kristine” mesh short, starting at $52.36, Amazon

Shorts for a Curvy Hipped Style Dial® 2

Balance out your curvy hips by drawing the eye upwards with a pretty patterned blouse and a statement necklace, while keeping the shorts simple and subdued. Look for a mid-width leg, minimal pockets (or sew them down) and avoid bulky button fronts. Look for a side zipper or tab closure instead. Angled pockets tend to open up, unless they’re sewn down, so avoid them when possible. Also avoid cargo pockets or any other extraneous details.

Vince side buckle Bermuda, $195, Bloomingdale’s

7th Avenue Bermuda shorts, $19.97, New York & Company

Sejour “Addison” stretch twill Bermuda shorts, $59, Nordstrom

Shorts for a Straight Style Dial® 3

The straighter lines of the Style Dial® 3 body type means that you can add as much detail and structure in your clothing as you like, provided you have the height to pull it off. (If you’re a shorter Style Dial® 3, scale back on the detail a little!). Flared, cuffed, drawstring and full flowy styles are all flattering, as are cargo styles, pleats, fun pockets and other embellishments. The key is to create shape with clothing. By adding fullness to the hip area with flared styles, you help define the waist and create the illusion of curves. If you are a plus sizeStyle Dial® 3, a flared or slightly wider leg can help highlight your legs while balancing out a fuller torso and bust.

Halston Heritage stretch double weave city shorts, $195, Amazon

Rebecca Minkoff “Santos” pique flared short, starting at $49.33, Amazon

Many of the shorts at Anthropologie are flattering to a Style Dial 3, like these Hei Hei pleated linen shorts, $78.

What to Wear if You Won’t Wear Shorts

As I mentioned earlier, shorts are not for everyone, or for every occasion. Whatever the reason, it’s nice to have options. Strangely, none of these options for shorts are actually short, but that’s sort of the point. The pieces shown here are versatile, comfortable and a little more covered-up.

Basics fold over rayon maxi, starting at $13, Amazon

Blue Pearl by Allen Schwarz crepe culottes, $69.97, Nordstrom Rack

RD Culottes, starting at $19.03, Amazon

I hope these tips have helped you to confidently choose the right shorts for your body type, or to skip them in favor of stylish substitutes. Either way, you’ll look cool and comfortable all summer long!