Piña Colada

Look, the chance to drink a Piña Colada like a man and not get ridiculed for it only comes once in a while. It’s called “vacation”. So, kick back in your beach chair and enjoy your bitch drink. Go ahead. We won’t judge you.

Shirt: Gitman Vintage Bamboo S/S ($200)
Nothing says “vacation” like Hawaiian-inspired shirt, but this one from Gitman Vintage won’t make you look like a complete cornball.

Shoes: Superga 2750 Cotu Classic ($55)
Classic canvas sneaker are another vacation essential. Beat ‘em up. These things are pretty indestructible and only look better with age.

Speakers: Jawbone Jambox ($199)
This fancy-shmancy bluetooth-enabled speaker plays music directly from your iPod directly, so you can blast your entire Jimmy Buffett collection with zero remorse.