Founded in the 90s with a story that backdates to pina coladas, Tommy Bahama is the clothing brand that holds the island lifestyle at the heart of their designs. A purveyor of the laid-back coastal life, the brand has become known for putting a casual twist on their active and sportswear collections. The result is clothing made with relaxation in mind. From their slip-ons, expect fuss-free styles that put comfort and function at the core of the design. Think classic boat shoes created in bold shots of color and driving shoes that come in soft leather.