If I had to name a few men’s fashion icons, Nick Wooster would undoubtedly claim a top spot. It’s rare to see someone his age not only dress impeccably but also carry such a commanding presence. Sure, Beckham is dashing, Adam Levine has swagger, and top fashion directors have their allure, but something about Nick Wooster sets him apart - he’d likely outshine them all.
Flashback to January 16, 2010: Nick Wooster, then 49, was serving as fashion director for a New York store. That day, he stepped out in a black-and-white herringbone blazer, rugged military boots, and jodhpurs that hugged his legs. He was on his way to a Milan fashion show.
Fate stepped in when two top street style photographers, Scott Schuman (The Sartorialist) and Tommy Ton, snapped Nick mid-stride and shared the photos on their blogs. Those shots quickly went viral, turning Nick Wooster into a street style legend overnight, even impressing the most seasoned fashion insiders. Now 55, Nick Wooster is a bona fide style icon. His every move is documented on fashion blogs worldwide - whether it’s his outfits, tattoos, hairstyles, or grooming tips. His Instagram following has skyrocketed to over 500,000.
Earlier this year, Nick added another feather to his cap by launching Wooster + Lardini, a clothing line created in collaboration with an Italian brand. Each piece in the collection reflects Nick’s unmistakable flair. “I must be the oldest startup founder in the world!” he joked.
Nick’s life is a whirlwind of travel, logging over 200,000 km on business trips in 2015 alone. New York remains his base of operations, with his tailor, barber, and shoemaker all conveniently located within 30 meters of his home.
Having worked for fashion giants like Ralph Lauren, Calvin Klein, and Thom Browne, Nick has perfected his style formula: half simplicity, half daring experimentation. It’s this balance that keeps him at the top of the game.
Now, let Nick Wooster take you through his style for five workdays, sharing tips and practical advice along the way.
Monday
"This is how I look after returning from an international trip. I like to travel with a lot of stuff, which usually means paying extra baggage fees. My travel essentials? Underwear, sunglasses, and grooming products. I always dress comfortably for the airport, but never sloppy - got to be ready for quick style changes if needed. In this photo, I’m wearing some relaxed Rick Owens pants, perfect for catching some sleep on the go."
Tuesday
"When I put an outfit together, I usually start with dark-toned pants, like chinos or cropped trousers. Then I add an oxford shirt in a light color like white or pale blue. I don’t iron them because I prefer the natural wrinkles. From there, it’s all about layering - shoes, blazers, outerwear. The bold blazer I’m wearing here is from my line. You need confidence to pull off something like this. Keep the rest of the outfit simple when you go bold with the blazer."
"First thing I do after a business trip? Visit Geno, my barber. I feel off if I don’t get a haircut and beard trim every two weeks. When I travel, I can’t always stick with Geno, but I always try to stay loyal to those who know me best."
Wednesday
"I don’t cook at home, so Morandi restaurant is my go-to. It’s a cozy spot just 30 seconds from my house. I’ve had countless meetings and lunches there, and they really take care of their regulars."
"I’ve tried dieting, but it’s not for me. I’m not a model - I’m just a regular guy. Being on the shorter side, I find Japanese brands fit me well. These wool pants from Sacai are a great example. The coat is from By Walid, which isn’t Japanese but has that same unique spirit."
Thursday
"I have tattoos all over, but none on my arms or neck - I want wearing a suit to feel clean. If I could do it again, I’d go for black and white ink only. Colored tattoos require way too much upkeep."
"I love cuffed pants in the summer, but I still wear no-show socks. Trust me, you don’t want smelly feet in stylish shoes. This Maison Margiela coat is a timeless piece for fall and winter. And bomber jackets? They never go out of style."
Friday
"Living in New York can be intense, so I make it a point to escape. The seaplane terminal is just 10 minutes from my place, and in 20 minutes, I’m at Fire Island where I rent a house. Sunglasses are a must whenever I’m out. I had eye surgery years ago, so I rely on brands like Garret Leight, Oliver Peoples, Moscot, and Ray-Ban."
"This shearling coat from Gucci is one of my favorites. It’s a big trend this winter, but I don’t think it’s going anywhere anytime soon."
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