Nick Wooster describes himself as a “free agent,” and given his long and storied career in the fashion world, it’s certainly an apt description. Born in Kansas, Nick now lives in New York City, where he’s a fashion consultant and director, having worked with brands like Barneys, Bergdorf Goodman, Neiman Marcus, Calvin Klein, Polo Ralph Lauren and Thom Browne, just to name a few. And if Nick looks familiar, it’s because he’s also a street style legend, with his unique fashion sense helping him create a fan base that looks to him for both timeless style and the latest trends. Nick took time out of his busy schedule (after we met, he was off to Berlin and Tokyo) to show us around his neighborhood of Hudson Yards and discuss how he pairs his Weejuns with the rest of his unique wardrobe.


You grew up in Kansas, far away from any metropolitan fashion scene. How did you develop your personal style?

I think growing up in Kansas forced me to be observant. I was always noticing what people wore in movies, magazines, and television. I was always dreaming about living in either New York, Los Angeles, or London. It was really my mom who first started me on this path. She wouldn’t buy me a cashmere sweater when I asked for one; she told me to work for one. So, I figured I would go to the source and started working at Joseph P. Roth and Sons Clothiers. That was my first job and my entry into fashion.

Your unique taste and style are one of the most respected in fashion and have been for a while. Is your personal style still evolving?

It’s always evolving. I’m never satisfied. Sometimes I look back at my tailored period and think it looked really nice. But then I put on a t-shirt and sneakers, because they are more comfortable. However, I do feel more like dressing up lately.

Do you have any advice for people trying to find their voice and style?

Practice. Practice. Practice. It’s always good to keep trying new things. Just know you’re bound to make mistakes. Keep pushing. It’s like going to the gym: one day, you’ll look in the mirror and be pleasantly surprised.

What makes a great outfit?

When something is a little bit off. Imperfection is actually perfection.

What makes Weejuns a staple in your wardrobe?

I got my first pair of Weejuns in 1976, when I was a sophomore in high school, and have always loved the ease of a penny loafer. They are an iconic staple that will never go out of style. There are not a lot of articles of clothing that can make that claim! I love that they can work with something from Comme des Garçons or something from Brooks Brothers. Weejuns are like the club soda of footwear—they go with virtually everything.

Nick's Questionnaire

Photography: Aaron Bengochea

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