top: Trouvé, shorts: Forever 21, shoes: Chinese Laundry, belt: Rachel Zoe, bangles: Lauren Ralph Lauren, longest gold neckalce: Kenneth Cole, star necklace: Gorjana

Shorts are more secure than a skirt. Sure bending over can still become a peep show, but don’t you feel just a little bit more safe touching your toes with that splash of fabric between your legs? My favorite time to sport shorts is an evening out. Obviously we are not talking your denim or your khaki bottoms. Leave your J. Crew pair at home. I am talking dressy shorts. You know the pair. They might be silky, patterned, leather, lace or just more fabulous than your average camp bottoms.

Once you have selected a pair of shorts for an evening out or fancy day event, pair your top accordingly. If your shorts are silky, add a silky top, like I have done at the Del Mar Races. That is not to say the fabrics need be of the same material, but make sure they are in the same tone. Don’t just pop into a cotton tee with your dressy shorts and then head off to a cocktail party. Dressy shorts means dressy top. It also means jewels. Put on those elaborate or elegant jewels to solidify your dressed up tone and don’t forget the heels. I am adamant about heels with fancy shorts. Of course elegant or funky flats will work as well, but nothing like a pair of heels with some shorts for an event.

Photo Credit: Robin Dayley/Dayley Photography