The Fitting Room Diaries: Shorts for All Shapes

Every few months, I seem to hear about the “thigh gap workout.” While part of me mentally sports a sweatband and goes digging for the thigh master in my mom’s old workout junk, the other part of me realizes that to achieve the coveted “thigh gap,” I’d need a plastic surgery lineup that rivals Heidi Montag’s.

But I’d keep my nose.

Anyway, what I’m trying to say is that I’ve got more of a “thigh overlap” going on. Which can make finding shorts that flatter rather difficult. But I love the look of shorts! In my mind they’re more comfortable than miniskirts. I pair shorts with tees, with chambray, with sweatshirts, with sweaters, with a tank and denim jacket but a small part of me always dreads putting them on.

I’m sure you’ve had a moment in your shorts wearing past where you’ve had to dig them out from their bunched up state in your nether-region. I admit I’ve done it myself and it is not a good look.

Before we get started, if you’re wondering why the “how to buy shorts” article is coming in September…

  1. Shorts are on clearance now so find your pair and buy one in every color possible.

  2. Shorts with tights and pumps or booties are an adorable look to help transition from summer to fall.

  3. Hold out hope for a beach vacation this winter… you won’t be able to find shorts as easily then!



To prevent this unfortunate and uncomfortable wardrobe malfunction, try shorts with a longer inseam. An inseam is measured as the length of your shorts or pants from the crotch, for lack of a better word, to the hem. Ideally, the inseam will be at least a half an inch, better yet a full inch, longer than the point where your thigh is biggest. For me, my thigh is biggest about 2.5 inches down my inseam so shorts with a 3 or 4-inch inseam are the best bet. Most retailers (J.Crew, Eddie Bauer, GAP, Old Navy, Banana Republic, LOFT) offer styles in multiple inseam lengths so once you know which is best for your stems you can stock up.

So while wearing my most comfortable pair of skinny jeans, I got out my trusty tape measure and started to measure my thighs. (Deep breaths.) I started by looping the tape around at the top of my thigh, right up against the inseam of my jeans. Then I incrementally moved the tape measure down slightly until I needed to pull it tighter. I marked that spot with my finger and then measured from my jean’s inseam down to that point.

Et voila.

It wasn’t pleasant and I definitely used centimeters because that makes the actual size of my thigh a little less real, but I learned that my thighs taper down after a few inches. So now I can shop with confidence for shorts that I know will fit better and be comfortable!


Pay attention to the rise of your shorts, measured as the length of your shorts or pants from the crotch, for lack of a better word, to the waist. Essentially, where the seams meet in your pants, down to the floor, is inseam. From that point to the waist band is rise. The rise is important to consider because too low of a rise, and you’ll get Barbie Butt (where your pants slip down exposing your backside like Barbie’s used to when she went to sit down in her pink corvette). You might find you like higher rise shorts (which are widely available now thanks to the 90s comeback). Higher rises will help to “contain” the area between your belly button and panty line. Rise is about comfort, and you should be able to get your thumb into the waistline of your shorts with them on and buttoned up. If you can’t, try a size up. Leaving room for your thumb will allow you to move easily and avoid the uncomfortable squeezing of your intestines.


Now a quick moment on fabrics: Linen, satin or silk crepe shorts are stylish and very comfortable but will wrinkle considerably where cotton, chino, wool, brocade or lace will stand up to wear a little better. That’s also to say you could wear a pair more than once… or twice… before having to wash and dry them again. Typically blended fabrics will have more stretch. Cotton blended with Lycra or Rayon have some give to them.


Let’s take a second and talk about short styles. Most retailers will offer “five-pocket” styles that mimic the fit and rise of a pair of jeans or trousers. These pairs usually come in chino or denim or cotton fabrics that are perfect for summer. Wear them this fall with your favorite sweater or sweatshirt and boat shoes for a casual seaside look or with a big wrapped sweater and sneakers for a cozy bonfire.

Shorts that are suited to wear with tights are going to be darker colored, patterned and/or textured. Some will have classic that classic “five-pocket” look I just mentioned, while, others will have zips at the hip or in the back. There are styles available with pleats, which make them look like mini skirts, enabling you to have that long legged look without dreading what you’d do if you drop something on the floor. And, skorts are not the awful thing they once were! Many skorts in stores today are stylish, and will be perfectly suited for fall styling.

And finally, unless it is your thing, I’d recommend not pairing shorts with riding boots. It might border on go-go. Instead, wear fall shorts with tights and pumps or ankle booties. Try to create a long line with your legs by keeping the shorts, tights, and pumps in a similar hue. Monochromatic legs create a straight, long line. This helps create that tall, elongated look we all love.

Now… we wanna see those gams! Post a picture of you in your perfect shorts and use the hashtag #TEGaPerfect10 to show us how you’ve mastered the look.
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