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Lucky Haul: Island Bound Edition

For the first time in quite a while, I'm taking a proper vacation. By proper vacation, I mean more than a 3-day weekend at my parent's house. Including a serious travel itinerary, passport requirements and a different climate. I'm bound for the tropics, where I hope to detach entirely from the rest of the world, indulge in some rum and you know, pretend I'm a pirate.

With the last of my Christmas money and a few gift cards, I trekked up to Barneys to see what I could find. And true to history, they didn't let me down.

First up, a Michael Bastian knit polo ($525) that will get mileage beyond a beach vacation. Pricey? Yes. Will I have this for at least 10 years? Yes. Your argument is invalid.

Next, I decided to get my shoe game centered. After several rounds of approval from Ray Siegel, I grabbed a pair of Mark McNairy laceups ($385) with a white sole. Lord knows that sole will get roughed up in a few wears, but I'll have fun doing it.

The last time I went on vacation, I dropped my hat in the ocean and it got wrecked. Luckily, J.Crew ($40) had a solid option available and in all honesty, I won't wear this unless I'm near water. I wouldn't be able to take myself seriously if I wore this around the city during the summer.

After this frenzy of shopping, I realized I hadn't bought a plaid shirt yet. So I remedied that with Gant by Michael Bastian's version ($185). Easy, breezy, tropical.