One of the reasons dress shorts remain so popular with celebrities is no doubt due to their duality: they're both daring and demure. While they're traditionally casual daywear, shorts are an unexpected choice for night, look quite chic when worn correctly, and are far more modest than a mini.
Whether you wear a loose blouse like Nicole Richie or choose a fitted top like Gwen Stefani, just make sure you incorporate some shine or slightly fancy fabric into your look. You can accomplish this in lots of ways; for example, pick a silky top (Rachel Bilson), satin shorts (Lindsay Lohan), or patent leather pumps (Mischa Barton). Also, as you're exposing a significant stretch of leg, you'll want to refrain from showing too much skin elsewhere-notice how the above ladies are otherwise pretty covered?
Stefani's own line L.A.M.B. currently make black velvet High Waist Shorts ($145) that are quite similar to the pair in the above image. We also like Chloe's Silk Blend Shorts ($540) as well as the tap pant vibe of the Satin Short Shorts by Elizabeth and James ($250). Topshop also has scads of super cute shorts, from the military-style of the Stripe Shorts ($60) to the cuffed and eggplant-colored Sheeny Pleat Pocket Short ($60).
Photo of Gwen, Splashnews.com. Photo of Lindsay, Pacific Coast News.