Shorts. They’re the bane of summer fashion for anyone who wasn’t blessed with the long, skinny legs of a prepubescent school boy (which was the exact person they were originally designed for.) But as warm weather approaches, we all need to come to terms with the fact that they are a staple of most people’s summer wardrobes and are thus a necessary evil. 

The good news is that you can choose from hundreds of styles, lengths, and fabrics to find a pair that suits you. The bad news is that you have to figure out which of those hundreds of styles, lengths, and fabrics will look best on a body that most definitely is not that of a prepubescent school boy. Here are some tips to keep in mind:

Finding the right length:

Woman's legs in shorts and high heelsThe key to feeling comfortable while wearing shorts is finding the right length. If you go too long, you’re running into either Granny fashion or surfboarding territory, and if you go too short, well, there’s definitely such a thing as “too much upper thigh.” Ideally, you want to fall somewhere between these two extremes, with a short that hits in the middle of your thighs (or just a few inches above your knees.) 

To figure out where that is for you, do the “sit test.” When trying on a pair of shorts, sit down on a chair the way you normally would, with your bum all the way to the back. Maybe you cross your legs, maybe you don’t. Either way, when you look down, are you exposing more flesh than you’d like? Sitting down requires the shorts to stretch to accommodate the new position, and if they don’t do that enough, then maybe you want a pair of shorts that are an inch longer. Another good test requires you to walk for a few paces. Do the shorts ride up in the crotch? If so, you’re not going to be comfortable wearing them out and about, and you should go a bit longer, or opt for a style that is tight with more stretch.

Figuring out a favorite cut or style:

Certain styles are, of course, meant to be worn at certain lengths or they just look strange. Daisy Dukes would look really odd if they were worn knee-length, and conversely, the palazzo shorts that are in style this year would look odd if they weren’t long enough. So once you’ve found the length of inseam (the measurement from the crotch of the garment to where the fabric ends on the inside of the leg) that you are comfortable with, you need to find the style that should be worn that long. 

Denim bermuda shortsAs we mentioned above, the amount of stretch also makes a difference. If you have thicker thighs, it’s often better to opt for styles that are worn longer and tight against the skin, like these bermuda shorts. That way when your legs rub together as you walk, the shorts won’t ride up and will provide protection against uncomfortable friction. These denim shorts look great and provide comfortable flexibility, even in the heat of late summer. And, because they’re meant to be tight, they don’t look ill-fitting on larger sizes as they would if wearing a style that’s meant to be loose.

Also, those of us with “talking thighs” can breathe a sigh of relief this season, because longer flowy shorts are definitely in. These linen shorts are universally flattering, if not wrinkle-resistant. Walmart even has a pair of cotton shorts that look really nice (and comfortable!) We are also seeing shorts like this everywhere, which are so flowy that they look like skirts but offer protection against any errant breeze-related wardrobe malfunctions.

If you prefer a more tailored look, J. Crew has the market cornered on chino shorts that look amazing while also being really comfortable. The only drawback is that they only offer a 4” inseam, which might be on the shorter side for some people. For a wider selection, Old Navy has a truly wide range of styles and lengths, and they list the inseam and waist lengths in the description so it’s easy to find what you want.

When you want to look casual:

Once you’ve found the shorts that you love it’s time to create an outfit. You might have noticed while shopping our links that many of the models are teens wearing tiny crop-tops. That is not your only option; take a deep breath. Any style can be amended to have a more modest aesthetic. 

Shorts with flora on themA tucked-in, fitted T-shirt looks good with almost any style short. But other options exist as well. If you prefer longer, tighter style shorts then flowy tunics can be great statement pieces. (Just be careful that the tunic isn’t longer than the shorts, or else it’ll look like you forgot to put pants on.) For the flowy shorts, try to find a top that is tighter so you don’t look as if you’re drowning in fabric. The basic rule to follow here is to balance flowy with fitted, regardless of which is which.

When you need to look nice

Hardy Amies, an infamously witty Savile Row designer in the 1960s once wrote: “The natural desire to relax is often the cause of the abandonment of all standards of taste; [one] should never wear shorts except [when] actually on the beach or on a walking tour” (The ABC of Men’s Fashion, 1964). Clearly, a lot has happened in fashion since then (thank goodness).

So, if you want to dress up a pair of shorts for something a little less casual there are plenty of options; it all comes down to your choice of accessories.

Woman in matching blazer and shortsBanana Republic is going for the trendy oversized version of wearing a blazer with shorts this year, although you don’t need to do the oversized bit (as unfortunately, that tends to only work with petite frames.) Going monochromatic with a blazer is also in vogue, but you can mix and match, too for a great, tailored look.

You can also dress up just about any shorts outfit with heels and have the added benefit of making your legs look longer. You could wear kitten heel slides or opt for more casual platform wedges.  Then just add an accent necklace or a light scarf and you’re ready to take on the world.

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