Nike SB Stefan Janoski Premium QS, $90

Luca Says: "The Janoski has become an instant classic; it skates great, has a super-sexy profile and looks good at yacht parties, too. I went to the Hamptons this weekend and everyone was wearing boat shoes. Luckily, I had my Janoski’s on so I totally fit in. I ended up eating a lot in these shoes over the weekend and I have to say, they make eating that much better. They really allow you to get in the zone and devour whatever is in your sight. I managed to finish 5 pounds of pasta that my aunt cooked in one sitting by wearing these shoes."