The First Date...

Destination:  Downtown Restaurant

Look: Keeps his eyes locked on you; leaving just enough to the imagination when wearing the Summer's low back with split midi dress (www.shelliscott.com), paired with a sexy sandal like the Giuseppe Zanotti - Alien, and the must have Christian Louboutin - So Kate Patent Leather Baguette Clutch.

Vacation Time

Destination:  Puerto Rico

Look:  For a sophisticated dinner outfit wear the Grace Maxi Dress (www.shelliscott.com) paired with the Jones Leather Tassel Belt (www.shelliscott.com), and a feminine pair of slides like the Tory Burch Tatiana's.