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.