If wearing shorts with heels is something you've always shied away from, then maybe it's time to give it a shot. It's all about the pairing, and can actually look very chic and put together. As with most good things in life, this combo is all about balance. Keep the shorts at least around a four or five-inch inseam, and think sophisticated, not bare on top. Adding a blazer makes what could be over the top more grown up sexy than spring breaker. Natural makeup and minimal accessories finish off this on trend, ladylike look. By the way, the heels I'm wearing are almost an exact dupe for the Valentino Rockstuds that would set you back a grand (view here). You could get them in a few colors and make your friends think you got a raise (or won a scratch off).
The Pricey Pauper