Mar 19, 2022 • 56M

The Perfect Shirt

Checking-in with Steven Alan.

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Michael Williams
Conversations about style, life, business and culture with interesting people.
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There really aren’t a lot of ways to reinvent a woven shirt. Somehow in 1999 Steven Alan found a way to do it. That was the year he created the Reverse Seam which would go on to sell tens of thousands of shirts. The innovation? To twist the placket and to reveal the outseam. It’s more than that though, Steven flipped the dress shirt to be a deliberately casual button-down. It’s not complicated, but the Reverse Seam was a important reinterpretation. It’s like going back in time two decades and popularizing the entire ridiculous idea for Untuckit. Only these shirts were for people who don’t hate themselves. (Sorry, I had to do it.) In all seriousness, a casual woven shirt was a great idea and that’s why Steven has sold so many of them and why Amy Larocca called it the perfect shirt, which I think sums things up fairly well.

My opinion is that Steven Alan is a legend. I’ve always loved his point of view and his Annex shop in Tribeca was my favorite shop in New York. His product was great, he brought in amazing brands from all over the world and there was always something great to discover. I mostly wear his other woven shirt, the Single Needle, since it’s a bit roomier and we collaborated to make some flap-pocket shirts way back when. They sold out in like 38 minutes. It was a bit of a dream collab for me because I love Steven’s general aesthetic.

Over the years Steven expanded the business to a point that became difficult to manage in a changing world. As wholesale and physical retail evolved Steven had to close all of his stores and the financial situation took him to the brink. He made some tough decisions to extract the company from the store leases and eventually he was able to recommit to a completely online only direct-to-consumer brand and web shop.

When the brand relaunched online Steven started making shirts in the garment center again and the Reverse Seam and the Single Needle have been resurrected. In a way the business has come full circle and Steven himself seems reinvigorated with the simplicity of it all. I’ve missed shopping at the Annex and seeing Steven in New York and was curious about the evolution of the brand. I reached out to Steven a little while back and we recorded a sort of impromptu podcast. Through our conversation we chart the early days of his stores and how Steven Alan has evolved through the years. Steven has had a huge impact of so much of what we see today. His brand is as relevant as ever, especially now that the Reverse Seam is back. Hope you enjoy our conversation.

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Thanks to Al James for lending me his music. The song is: Hard Working Dogs by Dolorean.