Before Steven Alan became a designer known for his stylishly rumpled button-up shirts, he was a merchant known for his eye.

Mr. Alan opened his first store in 1994, on Wooster Street in SoHo. He stocked that 500-square-foot space with vintage jewelry, Casio watches imported from Japan and Ugg boots (before they were popularized by the likes of Oprah Winfrey and Paris Hilton). He later added apparel from buzzy brands — Daryl K, Built by Wendy and Sofia Coppola’s Milk Fed among them — before starting a namesake clothing line and opening more stores in New York City, across the country and abroad.

At its peak, Mr. Alan’s domestic retail footprint included about two dozen stores, the majority of which he opened after a private equity firm invested in his business. But in 2019 he closed all his U.S. locations. Overseeing them while designing his own clothes and sourcing other makers’ items to sell became too “difficult for me to manage,” Mr. Alan said, adding that it got to the point where he would have had to sell more equity in his business to make a profit.

This month Mr. Alan, 58, is trying a sort of do-over with the opening of a new 500-square-foot store. The shop, on West 20th Street in Chelsea, joins the five other Steven Alan stores still in operation in Japan and South Korea.

Like his original shop on Wooster Street, Mr. Alan’s just-opened store carries a tight assortment of products he loves: vintage jewelry and watches, tubular T-shirts from the German brand Merz b. Schwanen, leather footwear from the Aurora Shoe Company. And, of course, items from Mr. Alan’s label, including his “reverse seam” collared shirts — named so because the internal seam is on the outside — which, in the late 2000s and early 2010s, found a customer base in bespectacled creative directors and Brooklyn dads alike.