The Devil Wears Prada, Love Wears Hilfiger Plaid

Tommy Hilfiger's Office

Do you like what you do and where you do it? This is Tommy Hilfiger's office, one of the many places on my Wednesday in New York where I asked myself those questions.

After our amazing morning at the Statue of Liberty, Ellis Island, and the World Trade Center site, we ate at a true New York Deli. It was called Stage Door Delicatessen, and the variety of foods was completely wonderful and overwhelming. Fruit, salad, deli meats, burgers, fries, milk, juice, soda, tea, coffee, dessert - everything you could imagine. You picked and chose. You called your order to someone on the other side of the counter, they prepared it in an amazing amount of time, you paid, and then you found a place to sit - perhaps around the corner and up some stairs to their second floor dining area overlooking the World Trade Center construction. The owner had a real live New York accent and she mentioned her brother Nick once as the other owner so that I felt I'd known them both all my life or at least grown up next door.

Full and happy, we made our way to a giant warehouse-turned-office-building for our Hugo Boss and Tommy Hilfiger tours. At Hugo Boss we shook hands with a man dressed better than any person I've ever stood next to in real life. He took us through the show room, which was now in construction mode for its twice-yearly renovation based on the seasons of fashion. (They change out the mannequins two more times a year for the pre-fall and spring seasons). That's four times a year the room gets a whole new look, two of which require nail guns, new carpet, and ceiling tiles. Can you imagine?

Alex - that was the guy's name - next introduced us to Sonya, also sharply dressed only in a breezy feminine way. I could almost see her walking to work that morning to the Raising Helen soundtrack. And this is the surreal part. Sonya has my job. She also tweets and runs the facebook page and generally takes care of the social marketing aspect of her company, only she does it in New York City under the name of Hugo Boss and can give away cool contest wins like trips to Germany. But it's okay. I get to give away...re-worded advice about student travel. Sigh. Yeah. It was surreal meeting her.

At Hugo Boss they gave us an idea of the tour they actually give to students. We heard some really fascinating history about the company, felt extremely welcome, and nodded along as if we can actually imagine their parties on the yacht and the fashion shows in Berlin. At Tommy Hilfiger we felt like those people you met at summer camp once and loved with all your heart but just haven't seen in a while, so you embrace them and bring them into your family room, plop them on the bean bag chairs, feed them snacks, and dish.

Our Tommy Hilfiger tour guide was John Burke. He got his job as the Tommy Hilfiger historian because he dug a pair of plaid ankle boots from a pile of castoffs and it made an impression on Tommy while everyone else had scoffed. He won't allow his picture to be taken because he stopped aging, but his face hasn't. And he told us all about how the Tommy people no longer speak to the Martha Stewart people in the elevator because the Martha Stewart people were eating cookies and laughing in their windows on the news the day the airplane pilot was rescued from the Hudson and the camera panned several office's floors just behind him. (Our office looked appropriately hopeful yet concerned, he said. The homeland security people looked grim per usual. But the Martha Stewart offices were practically having a cocktail party!)

John Burke teaches a course called Life 101, and we got little tidbits of it all along our tour, which consisted of cubicles and offices with walls, including Tommy's own corner office, where John proudly pointed out the custom artwork, portraits of rock stars - a community Tommy loves like John Burke and I love Hollywood - pictures of Tommy's wife and children (aren't they beautiful?), and the company closet stuffed full (though almost completely organized now by John and his interns whom I've decided might have the best summer jobs EVER) of hundreds of clothing items, from last season's sailor sweaters to a pair of jeans custom-made for Marilyn Monroe.

Through it all, John told us Tommy's history, the true American story, rags to riches, great idea to multi-million dollar enterprise. And he told us all about how you have to figure out where your passion lies and do that. "Success may not bring happiness," he told us. "But happiness can sometimes bring success." He literally overflowed with gems like that about the importance of doing what you love. As if I wasn't thinking about that enough as I strolled through real live New York City offices. I've always kind of thought that if you really love what you do it doesn't matter where you do it but that also if you really love where you work, it doesn't matter what you do. I don't think that's true anymore. Because as we walked by cubicles cluttered with fashion samples and sketches, I realized a cubicle is still a cubicle no matter what sidewalks lie below and you really better love what you are doing no matter what. John Burke taught me that.

And then it was over, because despite how much I loved John, I had now begun a frantic texting session with Agent Holly followed by quick advice from Matthew the Super Guide, because as wonderful as John Burke was, he had just made me late for a meeting with Holly at an adorable independent bookstore way too far away. Coming up: A delightful walk through Chelsea to Holly's plan B and the part of my trip that made my mother ask, "Will the rest be a letdown for you now?" And I responded, "You mean, the rest of my LIFE?"

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A Wednesday in New York