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The key word in that last sentence is we. While De la Renta’s company bears one name—his own, punctuated by his famously suave signature—it has become a family affair. We, specifically, constitutes two people in particular: Eliza Bolen, the youngest daughter of De la Renta’s second wife, Annette, and for ten years, vice-president of the $250 million licensing department, and her husband, Alex Bolen, who was named the company’s chief executive when Jeffry Aronsson jumped ship for the corporate gloss of LVMH after nearly a decade with De la Renta. Spend time in De la Renta’s bustling, creamily lit headquarters, one of the last where wrinkled seamstresses hunch over drafting tables stitching the clothes in-house—and you’ll hear a great deal about how we are changing De la Renta. We are involved in exciting new developments (in addition to O Oscar, there’s a fledgling home collection overseen by Miles Redd). We are only starting to tap into our true brand recognition (a Madison Avenue boutique opened in November, followed by Miami, with Las Vegas on the way and Europe in the crosshairs). We are hoping to turn an elite brand into a global empire catering to a larger clientele (much like Ralph Lauren, to name the visionary designer we most admire).

Bolen’s appointment was something of a shock: Was he really the best man for the job? Or was this merely the crass hand of nepotism? A carnivorously ambitious, West Virginia–raised 37-year-old, with close-cropped sandy hair, he has no background in fashion. (Which is becoming more commonplace; Robert Polet, Gucci’s new CEO, comes from the world of frozen foods.) He worked in finance, founding and then selling an asset-management company before joining Bear Stearns, and, as the market stalled, consulted part-time for De la Renta while the designer searched for a new CEO. It didn’t take long for Bolen to win over the fashion set. “A lot of what you’re seeing with Oscar has to do with Alex coming onboard,” says Wintour. “He’s come up with some kind of master plan to expand Oscar’s empire, and I think it’s a correct one. Oscar deserves a bigger platform.”

“When the chief-executive offer first came up with Oscar, I was more than a little hesitant,” Bolen says, sitting in his corner office, adjacent to his wife’s. “Working with my wife, with my father-in-law—it just seemed like a recipe for disaster.” Furthermore, the fashion world is populated by a different personality type—affectedly eccentric, unpredictably sensitive—than he was used to on Wall Street. “On Wall Street, let’s face it, everything is motivated by money,” he says. “In fashion, everyone understands it is a business, but you’re still really dealing with . . . I mean, these people are really artists. I think, for me, one of the biggest challenges has been learning patience, and how to manage personalities.”

The personal dynamic between Bolen and De la Renta is a curious and entertaining one to observe. De la Renta likes to joke, always in the presence of his son-in-law CEO, that Bolen will one day fire him. (“I think you’re safe for a few more days,” Bolen replies.) Bolen, who always seems to be within fifteen feet of De la Renta, barking about various business coups and pitfalls, often can’t help but make design suggestions. (“Alex,” De la Renta replies, “fashion school is on the corner. I believe they have night classes.”) As personalities, the two are polar opposites. Bolen wears a tie because he’s the boss; De la Renta because “it’s one of my very few complexes. I see people in a colorful shirt and I think, My God, I would really love to wear that, but then I am afraid that when I walk into the door, the host will say, ‘I’m sorry, but the Latin band walks through that other door.’ ”

De la Renta likes to joke that his son-in-law Alex Bolen will one day fire him. “I think you’re safe for a few more days,” Alex replies.

The designer’s capitalistic urges are cloaked by courtesy, indefatigable charm, and an ability to talk for hours about the texture of fabrics. Bolen is brusque, fast-talking, a natural-born intimidator who turns almost any subject of conversation into one about the business’s future. (As it happens, employing his stepdaughter and son-in-law almost never became an option: When De la Renta asked Annette to marry him, in 1989, she didn’t say yes immediately. “She didn’t want to get married,” he says with a laugh. “She thought there was no need to. But I’m a Latino, so I believe in the institution.”)

The Bolens’ effect on the De la Renta identity is most evident in the designer’s recent—and successful—push to court younger women. Eliza Bolen will often look at his designs and proclaim, “My friends will never wear this,” at which point De la Renta does some rethinking. At the same time, the designer views his current renaissance in sociocultural terms, defining himself as something of a postfeminist designer who made his mark in a prefeminist age. “Certainly, what is exciting about fashion today, especially in my field, is that never in history has there been a time when a woman has as much control over her destiny as she does today,” he says. “I always tell this story: When I started, the woman went to the store to buy a dress. She saw it in pink and red, and then she remembered that the husband, who is probably going to pay for the dress, loves it in pink. So she buys the pink. Today, the same woman goes to the store and remembers the husband likes pink, and she buys the red.

“I think that probably what has made my business so successful today is because the most important consumer now is the professional woman,” he continues. “Back in the seventies and eighties, she was going into the men’s world. She felt she had to dress in very, very boring clothes. And then, you know, a woman knows that she can look great, that being a woman is an asset. And this is what I have always known. And so, perhaps, this is my time.”

It’s been rumored that the true motive behind the current rush of activity is to ready the company for a sale, and while Alex admits that “the crude fact is that everything is for sale, for a price,” he is adamant in pointing out that “there is no endgame plan,” adding that keeping the business in the family is critical to preserving the De la Renta identity.