Your Body + Shorts, a Love Story?

When your legs are your frenemy

I’ve never loved my legs. My thighs and I have always had a complicated relationship (mostly me wondering why they wouldn’t shrink). So naturally, shorts and I have been on the rocks for some time. But shorts are a critical part of the summer wardrobe! So today we’re talking about the styling tips that make shorts work in your favor so you can actually feel good wearing them. Even if your legs are long and lean, and your thigh gap is a mile wide, some shorts are just bad news. Here’s how to win the shorts game.

Me, age 4, rocking my shorts and here for the fashuuuuns!

The bigger the X, the smaller the Y

Let’s talk proportions: the bigger the bag, the smaller you look in comparison. The more voluminous the shorts, the slimmer your legs appear. It’s not about hiding; it’s about contrast. Oversized pieces create balance, making everything around them seem more delicate, and yes, smaller.

Jessica Simpson, Patron Saint of “The Bigger the Bag, the Smaller the Girl”

It leads us to…

Rule #1: Size up when buying shorts

Free People tank / The Great shorts M / Amazon socks / Salomon sneakers / The Best Hat paracord string

I generally wear a small in clothes, but I always buy a medium in shorts. It’s not because shorts are more comfortable when they’re bigger - don’t be crazy you know I don’t think like that. It’s because shorts look better when they’re roomier. Especially when you sit down. This principle applies practically across the board, but really works when it comes to sporty shorts like the ones above, or these from Adidas, or boxer style shorts like these from Comme Si (every fashion girl’s favorite).

Hat / The Great tank / Free People shorts / F&E Sweater / Miu Miu boat shoes

Rule #2: Flare out

Shorts with a wider leg opening create a visual contrast that makes your legs look slimmer. When the fabric floats away from your legs instead of clinging to it, you’re avoiding a potential stuffed sausage scenario. A little breathing room goes a long way.

I wore these shorts on the first hot day we had this week and I got so many compliments! I felt like my legs had room to move and the shape is so cute. Doen top / Vince sandals / Jenny Bird anklet

Rule #3: Make geometry work for you

The more a short flares at the sides, the longer it makes your legs look. We’ll call these “optical illusion shorts”. This is basic geometry, but also kind of a magic trick:

Ganni shorts on the left with a nice flare at the corners. The sad, flat shorts on the right are from Everlane.

My favorite optical illusion shorts from Free People (and they’re $78!) it’s a style they’ve had forever and I reach for them every year (wearing a M). Soldout NYC tank (M) / Frame belt (code ABBY15) / Bottega sandals

Another cute pair from Natalie Martin (M) / Maison Irem necklace / Shashi earrings

Part II: Controversial shapes

Every summer a few controversial shorts styles emerge; and I say controversial because they’re hard to style. The category includes capri shorts (sausage makers) and bloomers (diaper butt). This year it’s the “dad short”.