I used to rail against pleat-front anything - men's pants, ladies pants, skirts - you name it. I've definitely come around and I'm hunting for the perfect pair (or pairs) of pleat-front pants. But it can be a tricky proposition, the waistband must fit perfectly (ill-fitting baggy and pleated is a recipe for oddly fat looking thighs), the fabric must drape nicely and there can't be any crazy embellishment.
These remind me vaguely of great Colonial-era jodhpurs (without the insane thigh bulge). They pouf just perfectly above the knee in a great, soft gather.
The cropped pant tends towards casual, but worn with stellar heels these would look dramatic and definitely dressy.
City Style silky pleated ankle pants, $12, New York and Company
I'm always a sucker for the super high-waisted/wide leg combination. I'd pair this with a slouchy grey American Apparel v-neck and some layered necklaces.
Jean Paul Gaultier Wide Leg Pants, $114, zappos.com
This is the quintessential golf short that is probably the root of my fear of pleats. Typically, I see these on people who actually fill out the pleats as if they were added to accommodate extra body mass so you don't have to size up. Incorrect. They are infinitely more flattering if they drape loosely against the body. I love this casual, slinky pair. Love them.
BR monogram bloomer short, $100, Banana Republic
Getting into the potentially oddly slouchy/baggy category here, but the stiff wool material and properly fitting waistband make me think these could be really cool in an architectural way.
Alice + Olivia Arthur Pants, $275, Shopbop.com