Jean shorts - our moms wore them in the 50s, and the 60s. Many of us wore them in the 80s, then again in college in the super grungy early 90s (with tights, natch) and now here we are in 2010 ... do we or don't we? To jean (short) or not jean (short) that is the question... and let me tell you 'tis far nobler to wear what works than to suffer a fashion tragedy. That said, they' are incredibly versatile and practical so maybe its really a question of HOW and not IF.
My pick is this pair of Red Engine 'boyfriend' shorts or something like them. Understated, comfy, and a far cry from the...er... "WT" Daisy Duke cousin that's given them a bad name. Of course I'm not going to really drop $100 plus on a pair of neatly rolled-up cutoffs, so I'll grab the Old Navy version instead. My advice is to go with something mid-thigh, with a looser cut (like a boyfriend cut). Skip the frayed edges and the pockets hanging out below and for God's sake, cover your butt (and then some). I'd pair with a detailed belt and long-sleeved t-shirt or woven top and a pair of flat sandals. Less is more. Trust me.