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Jason Alexander didn’t plan for a career in fashion. London-born and St Lucia-raised, Alexander had earned a university degree in business, moved to New York, and was working on Wall Street when he found himself pulled in an entirely new direction. “My job was on Wall Street but it wasn’t something that I was passionate about. I made money, but I wasn’t passionate about it,” he said. A part-time offer to assist a friend at Fashion Week led to a 20-year career in high-end retail, styling, and menswear — the pinnacle of which is Alexander’s newest project, the brand-new Style On J boutique on 9th Avenue.

Jason Alexander welcoming Hell’s Kitchen neighbors to Style on J on 9th Avenue. Photo: Phil O’Brien

The new menswear boutique — specializing in the latest trends direct from the streets, bars, and clubs of Hell’s Kitchen — is the product of Alexander’s many years as a stylist and creative director for stores across the city. “When I got into retail, I did the big boutiques — Barneys and stores like that. And I realized that’s not where I wanted to be — I love a small boutique because I can be much more creative than I could in a big store where you’re so controlled and monitored,” said Alexander. 

After managing and opening several stores in Chelsea, “I asked myself, ‘Why am I making other people so much money? Why shouldn’t I have my own store?’” he laughed. The decision to carve out space up 9th Avenue was a natural one to Alexander, already a keen observer of the queer community’s social and cultural trends. “I know my demographic very well,” said Alexander. “I’ve seen the transition from Chelsea into Hell’s Kitchen. I saw most of the bars come here, most of the restaurants come here, but it was a slow process. My demographic was slowly moving here over the course of the last 10 years, and now the majority of my demographic is here,” he added. 

After a long pandemic wait, he was able to secure a space in the neighborhood and began building his brand — a process that came easily to Alexander after decades cementing his reputation as a stylist. “I decided to call it Style On J, because that’s what I do. Some of my clients are fashion people, and some are not, so it’s often a process of me grabbing stuff and putting an outfit together. What I love the most is when someone asks, ‘Can I have the outfit on the mannequin?’” he added. 

The thrill of styling clients brings Alexander back to his first days in the fashion industry, when he accepted that fateful part-time gig at Fashion Week. “I was being an assistant for a friend of mine at Mercedes-Benz Fashion week —  I was literally just putting shoes on a model. And it was so exciting, the thrill of everybody rushing and everybody running out there, that just got me going and I never stopped being in it — I was always drawn back into fashion,” he said.

Jason Alexander at his new store on 9th Avenue. Photo: Phil O’Brien

He honed his craft working as a creative director for catalog brands like collegiate giant MV Sport, as well as styling looks for celebrities — “some nice and some not-so-nice, but that’s part of the job”— before branching out into retail. His skills as a stylist proved indispensable when it came to mastering the buying process, a capability that Alexander prides himself on. 

“When I ran a couple of stores, I did most of the buying process myself. Now, because I’m dealing with a relatively small space, I know I have to be very effective in buying — I know what my clientele needs, so I tend to bring in exactly that,” said Alexander, crediting his sharp observation of neighborhood trends as real-time market research. 

“I pay attention, I follow trends. I look at every season’s designs, see the runway shows when I have the opportunity. I also go to the bars, the parties —  I want to see what everyone is wearing, what they’re not wearing, what they like — it’s why my buying skills, I think, are very effective,” said Alexander. “I believe the minute you stop doing that, you’re done. I am of the belief that you should never think that you know it all — even if you’ve been in the community for a long time. You still have to put yourself out there and pay attention to what the boys are wearing, what the new trend is, and get involved. That’s how you’ll always be on top of it and it’s one of the keys to success — and it’s fun!” he added. 

Alexander believes that providing his Hell’s Kitchen clients with candid, solutions-oriented styling advice is the key to developing a loyal customer following. “If something doesn’t look good on the client, tell them the truth,” he said.  “But don’t tell them the truth and walk away — give them options! And that’s what I’m very well known for — I’m a stylist first. Because if I tell you look amazing and you walk out there and your friends tell you look amazing, you’ll find me wherever I am, because you’ll always want my opinion,” added Alexander. 

Thus far, the neighborhood is eager to hear Alexander’s advice. Since opening, Alexander says he’s been inundated with local support, adding that West Siders are thrilled to have a rare clothing boutique in the area. “I’ve gotten a lot of positive reactions —  I’ve been getting a lot of retweets,  I’ve been getting a lot of Instagram posts, people shouting me out — I very much appreciate it! It’s been a little wild,” he said. Everybody’s like, ‘Oh my god, finally! There are so many bars, so many restaurants, and no men’s clothing stores’.” 

He also cites the warm, welcoming, Hell’s Kitchen business community as further reason to stay: “I was floored at how many business owners have stopped by, saying, ‘Hey, if you need anything, let us know — and welcome!’. From just this block alone, I’ve had so many supportive business owners literally coming in and bringing their clients to be my clients. I told them, ‘Whatever way we can work together, let’s collaborate.’’ 

While it was an unexpected path to 9th Avenue, Alexander hopes that Style On J is simply the start of a new and fruitful chapter of his fashion career. “It’s been a whirlwind — Style On J is my first baby,” he said. “I’m so fortunate that I was able to find something that I love, because I know it’s a rarity for a lot of people. I’ve been doing it for almost 20 years now, and I still love it!” 

Shirts on display at Style on J on 9th Avenue. Photo: Phil O’Brien

Style On J’s current opening hours at 746 9th Avenue (between W50th and W51st Street) are Monday to Saturday, 11am to 8pm and Sunday 12pm to 7pm

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