Pleat it

At some point in the last year, I became obsessed with menswear. Not watching men's clothing come down the runway necessarily, but actually absorbing aspects of menswear into my own wardrobe.

It started with nautical stripes, moved into oxfords, then grew into boyfriend-fit everything, from slouchy jeans to oversized t-shirts, and now I'm fixating on shorts. Specifically pleated shorts. We're talking the roomy, high-waisted, sometimes cuffed, pleated shorts your dad used to wear golfing. They've gotten a bad rep over the years, mostly due to middle-aged mom wearing them into the ground. But who can blame them? Pleated shorts are comfy as hell, flattering on many body types and popping up everywhere. Check it:

 Steven Alan shorts from Net-a-Porter

Look how cute they look with a fitted top. Tucking in shirts is key with this look. Go untucked and you've ruined the appeal. Also, make sure you wear them in a size that stays roomy in the legs. These aren't meant to be hotpants, and you don't want the pleats to stretch out and become, well, unpleated. I was worried about this at first because I tend to have a smaller waist and bigger hips, but I haven't had a problem with the styles I've tried so far; in fact, I think they're flattering on my body type, which is part of why I love them so much. Vintage styles fit me best.

Creature of ComfortSee what I mean by menswear-inspired? This chick looks like she's about to play a game of croquet with a cigar in one hand and keys to the yacht in the other. I'm guess I'm mostly inspired by upper-class prep-school menswear, come to think of it.

Photo by Meghan McAndrewsAbove is a shot of me in some similar thrifted pleated khaki shorts. I got these suckers at a Salvation Army for around $2. They're super comfortable and look cute dressed up or down.

Frances MayHere's another similar pair. Throw on a skinny belt, necklace and some sandals and you have yourself an outfit.

Jenni Kanye from ShopBopI just thrifted a pair similar to the above shorts for $2.50 last weekend. They were a little longer than I wanted, so I cut them right below the top hem of the cuff. After washing them, they wound up with a cute fray along the bottom, giving them a slightly rugged feel. I look like I'm about to embark on an African safari. Awesome.

Elizabeth and James from ShopBopHow cute are these? They have just the tiniest bit of pleating and sit low on the waist, but I love them anyway.

Photo by Meghan McAndrewsHere I am with a pair of similarly lower-rise shorts. These puppies are crazy comfy and maybe even a little big, which is why they sit so low on my hips, and why I wear them cuffed. Eh. I bought 'em for a couple bucks at a Salvation Army, so sizing gets a pass.

Creatures of ComfortAnother black variety, but high-waisted and with what appears to be elastic in the sides. Don't tell anyone, but the black shorts I'm wearing above also have a bit of elastic in the sides. How downdy, right? Wear a belt and no one'll ever know.

Chambray B3 from Need SupplyAck, how cute. Love the styling in this look. I'm not sure what you call this type of puckered, belted high waist, but whatever it is, I love it.

Photo by Meghan McAndrewsLast but not least, here's a shot of me in some thrifted linen shorts. This pair wrinkles easily and sits super high on my natural waist — also uncomfortably so. But they make my legs look six miles long, and I can wear 'em with anything, so it's totally worth it. As always, secondhand shorts straight outta the '70s, '80s and '90s fit me best. And who can beat the $2 price tags?

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