There isn’t a sandal more classic or iconic than a pair of Jack Rogers. I love seeing old pictures of Jackie O. wearing hers during summers on the Cape! I order a new pair of gold Jack Rogers every season – they go with everything and are so comfortable once you break them in. To celebrate its 55th Anniversary, Jack Rogers created a special video series featuring real customers, and the brand is also giving away 55 pairs of Classic Jacks. You can enter for a chance to win one of the pairs here!