When Ralph Lauren and Oprah Winfrey sat down for a tête-à-tête on Monday night at New York City’s Alice Tully Hall, the two American icons picked up where they left off last spring at Lauren’s Colorado ranch, where Oprah interviewed the designer during the last week of her show.

“It took me 25 years to get an interview with Ralph Lauren,” she told the audience at the start of the black-tie event, which raised more than $7 million for the Ralph Lauren Center for Cancer Care and Prevention in Harlem and the Lincoln Center for Performing Arts. A crowd of celebrities, designers, socialites, and media bigwigs turned out to watch the live chat and enjoy a gala dinner in honor of Lauren’s career and commitment to philanthropy.

“You don’t often get Oprah out on a school night,” said Gayle King shortly before the pair took the stage. “But when Ralph Lauren asked her to host this event, there was no question that she would be here. They’re very close friends.”

As guests convened in the hall’s glass-windowed lobby for a champagne reception before the theater doors opened, several reminisced about their first Ralph Lauren purchases. Lauren Bush, who is married to Lauren’s son David, recalled a pair of chinos she bought in grade school. For actress Camilla Belle, it was a simple boy’s blazer.

Designers showered Lauren with praise. “He inspires me in so many ways,” said Tory Burch, who staged her first official runway show in the Alice Tully Hall lobby in September. “It’s amazing to think what he’s done for our industry and for philanthropy.”

“He’s built this unifying line of democracy between art and commerce, and he’s rocked it so well,” gushed Prabal Gurung, a young designer whose meteoric rise has dazzled the fashion industry since he launched his first runway collection, for fall 2010. (He’s already dressed two of the most powerful women in America: first lady Michelle Obama and Winfrey.) “The longevity of Ralph’s career and business is both an aspiration and an inspiration for me.” As for Oprah’s role as host, Gurung hoped the talk-show veteran would prompt Lauren to reveal some of the secrets to his success. “I just want a few formulas that I can take back to the office,” he whispered.

Martha Stewart, Barbara Walters, Naomi Watts, Uma Thurman, Seth Meyers, Michael J. Fox, and Brian Williams were just a few of the famous faces in the crowd. Jerry Seinfeld breezed in with his wife, Jessica, moments before the show started, pushing past photographers who didn’t notice Anna Wintour slinking stealthily into the theater with rumored partner Shelby Bryan trailing closely behind.

Wearing a satin red collar gown, the hostess took the stage to announce the man of the hour: “He designed the fabric of America as we really all know it today,” Oprah said. “But we’re here tonight because Ralph Lauren is more than just a tastemaker—he’s a lifesaver.”

Oprah got Lauren to open up about his close friend Nina Hyde, a fashion editor whose battle with breast cancer inspired him to raise awareness about the disease more than 20 years ago. As to how he became, in Oprah’s words, so “darned” American, and how he’s managed to sustain his brand’s sterling image for nearly 45 years, Lauren credited his humble roots and dogged determination. “I never went to fashion school, I never had the training. It came from inside. I know what it’s like to yearn for something and not have the money to buy it.”

While Lauren’s aesthetic has garnered a reputation as “classic” (a word he deems somewhat “boring”) and quintessentially American, the designer himself embodies the American sensibility more than his clothes. Like Oprah, he’s lived the American Dream.

After the chat, The Daily Beast caught up with a beaming Jessica Alba on her way to dinner. “There’s something to be said for hard work and not wavering on one’s vision. Sometimes things like that are overlooked.” The actress has worn Ralph Lauren on many occasions, including at this year’s Met ball while pregnant with her second daughter, Haven. “I’ve never worn velvet before,” she said, running her hands down the black strapless gown with a beaded bust she’d picked for the night. “And all these jewels up in here,” she added emphatically, shimmying to reveal her assets before her husband, Cash Warren, whisked her away through a sea of VIPs.