Funny story: I've added 3 little black dresses to my closet in the past 12 months. That brings my total count up to 3. They are all vastly different. First is a knitted dress by Phillip Lim, shown here and in this post from Greece. The other two are both Jason Wu, one is a shirt dress, the other is a little more modern (I just bought it so I don't have an outfit post to share.) One thing they have in common is a fun little twist. This particular dress has a cute tie-front and a flap in the back that moves to show a little bit of skin in the wind. Also, all three were purchased at Roundabout Resale in Westport.
Dress: 3.1 Phillip Lim (Roundabout Resale), Loafers: Burberry Prorsum (Net-a-Porter Sale), Necklace: bought in Santorini