After 16 years at J. Crew, Somsack Sikhounmuong switched to a much smaller company to design clothes for Alex Mill. But he's remaining close to the Drexler family. "I always joke that he's my fairy god agent," said Sikhounmuong about Mickey Drexler, the former CEO of J. Crew Group. During a sabbatical after his work at J. Crew and Madewell, the J. Crew subsidiary that continues to outshine its parent company, Sikhounmuong got a phone call from Mickey Drexler: "I was in line at Whole Foods, because I wasn't working and I could be in line at Whole Foods in the afternoon," he said. Mickey asked him to meet with his son Alex Drexler about designing for Alex's company, Alex Mill, for which Mickey Drexler is both an investor and an advisor. On the Glossy Podcast, Sikhounmuong discussed his work for Alex Mill, which was founded in 2012 out of "a tiny store on Elizabeth Street." Sikhounmuong also talked about the difference between designing clothes for women versus men, the transition from a massive company to a startup, and the experience of interviewing with J. Crew's Jenna Lyons.

With the recession in full swing, 2009 was a tough year to start a luxury brand, as Ledbury CEO and co-founder Paul Trible knows. But Ledbury bet on luxury, at a price range that invited both younger customers to step up their wardrobe, and older ones to save money, compared to what they were buying. "That's anywhere between $125 to $185," Trible said on the Glossy Podcast. "It's still expensive for folks, but what we saw very early on is we were pulling people down from Canali and Zegna and Eton, people who were spending usually $250 or $300 a shirt." Direct-to-consumer makes up 70% of Ledbury's sales, Trible said, with another 20% coming from wholesale. Brick-and-mortar stores -- of which the company has three -- fill in the rest of the revenue pie. On this week's Glossy Podcast, Trible spoke about quality manufacturing, a unique revenue-sharing model Ledbury started with its retailers and fact that the second button is what makes or breaks a shirt, just like Jerry Seinfeld said.