It's not often that I deliberately revive the 80s for my personal wardrobe, but when I saw these classic Gap "easy fit" (haha) pleated khakis going for a fiver in a local charity shop/thrift store, I couldn't resist. Three years, even a year ago, I would have turned up my nose, but thanks to rising waistlines and an easing-off of pleats as fashion anathema, the time seems right to go there once more.
How to style? There's history here. After WWII, when returning soldiers popularized them for wear on campus, the ideal was with a crisp white or blue oxford-cloth shirt, or, for a more James Dean-y vibe, a blindingly white t-shirt.
When Diane Keaton was dressed by Ralph Lauren for Annie Hall, the look jumped to the women's department, while keeping a menswear edge with a vest , tie, and brogues. Neither incarnation is going to work perfectly for me but what I will do (much as trying-harder fashionistas are doing this season with the dreaded harem pants) is keep the upper half as close to the body as possible, possibly with layered tees. Sleeveless shirts would also work very well. On foot: sandals--pretty ones--because as much as I love easy fit, fashion's gonna come in there somewhere.