$253, asos

Skimpy and leather are two words that I don't usually like together--except in this case. In fact, I have a dress that's very similar to this one in white, which I wore to a wedding last year in Palm Beach. (You can see me in it here.) There's no doubt this is va va voom sexy and definitely more appropriate for the minimally-endowed, but the fullness of the skirt keeps it tasteful. Come colder weather, I also like the idea of wearing a black turtleneck underneath or a cropped sweater over it. But for now, I'd pull it off like this...

1. Asos leather dress, $253, asos.com
2. J.Crew cardigan, $89, jcrew.com
3. Burberry Prorsum clutch, $1595, netaporter.com
4. Aquazurra peep-toe booties, $595, shopbop.com