I pretty much stopped wearing shorts when I stopped going to camp, but if there's any time to bring them back, it's summer 2009. The hideous romper trend is proof enough that shorts are replacing skirts and dresses as the preferred method of showing off your legs.
I love a pair of jean cut-offs as much as anyone (except when the pockets are longer than the hem, and poke out at the bottom--I think that is the tackiest of the tacky. Makes you look like a white-trash teen who took a pair of blunt scissors to her jeans and just cut them as high as possible in order to seduce pimply boys at the outlet mall), but right now I think different fabrics and styles are worth investigating. These Gap button-tab striped jeans, $24.99, are menswear-inspired but still playful enough for girly girls. I like how they're a little bit longer, so you don't have to feel overexposed when you're riding the subway.
On the other hand, if you're not afraid to flaunt your killer legs, there's the Zimmerman Jinx Chambray Short, $55.20. The light blue color matches the sky of a classic summer day, and beaded drawstring on the side adds a crafty spin. I'd want to wear this with a loose, billowy white top, and then maybe some black gladiator sandals with silver studs--you know, to add a little toughness so you don't look like a member of The Babysitter's Club (Dawn was the California hippie, right?).
If there's one thing I believe about shorts, it's that they should be cheap because they're not very versatile. You can't wear them to work (unless you're a classy man rocking a nice shorts suit), or nice restaurants, or any month in which the temperature dips under 60 degrees. A trend I hate almost as much as rompers? Wearing shorts over tights in the winter. On the other hand, I do prefer that wacked-out layering to just wearing tights and a shirt, which, ladies of New York, IS NOT APPROPRIATE FOR PUBLIC.
Where was I? Oh yeah, shorts could be dirt cheap. Enter Old Navy! Their always-reasonably priced shorts are now on sale, and I want to get the Low-Rise Perfect Khaki Shorts, $12.99 to $7.99, in every color. The bright white is perfect when I want to go all-out nautical (stripped navy blue boatneck top, a gold anchor necklace, some leather boat shoes, perhaps a scarf used as a headband), the classic khaki is good for hanging with the family, and the jalapeno green is perfect for drinking Coronas with friends at a patio bar.
I can't end this post without including denim. From American Eagle, the Tuxedo Short, $29.50, has a silly name but a great design. It's a bit distressed, so it has that lived-in look without being on the verge of falling apart. The waistband is cummerbund inspired, which distinguishes these shorts from other basic pairs, and you really can't go wrong with a dark wash and a 2-inch inseam.