Philip Green has a problem with four purple crushed-velvet dresses hanging from a display stand.   “Here’s one of my pet hates: too many garments on a rack,” Green says, thrusting the frocks at Becky Bateman, manager of UK fashion chain Topshop’s flagship London store.

It’s a Thursday morning in early October, and Green, 57, has strolled down London’s Oxford Street from the head office of Arcadia Group Ltd., his privately held retail clothing company, for a store inspection.

That’s the kind of attention Green has also lavished on Topshop’s first US outlet. In April, he flew supermodel Kate Moss to New York to open the 2,323-square-meter emporium in Manhattan’s SoHo neighborhood that he says cost $25 million to prepare.

The British billionaire is rolling out Topshop at a time when Americans are holding tightly onto their wallets. Total US apparel sales dropped 7 percent in the first six months of 2009 to $85 billion compared with the same period last year, according to NPD Group Inc., a New York-based industry research firm.

Green has the cash to back the expansion in a country that has been a graveyard for British retailers. Since 2000, his family has taken about £1.8 billion ($2.8 billion) in dividends from Arcadia and Bhs Ltd., his privately held UK department store chain. Green owns Arcadia through Taveta Ltd., a holding company registered in the British offshore tax haven of Jersey in the Channel Islands, and his personal fortune is estimated by the Sunday Times of London to be £3.83 billion.

Arcadia has all of the resources it needs to make acquisitions, Green says. The group made a profit of £164.7 million on sales of £1.9 billion in the year ended on August 29, 2009. Topshop and Topman, a so-called brother brand for young men, contributed more than a third of the group’s revenue for that period. In the same year, Arcadia’s bank debt fell 23 percent to £535.8 million, the company said on October 22.

Green’s dealmaking over the past three decades has transformed him from the Bond Street Bandit—the name of an early store—into a billionaire tycoon with a knighthood and a roster of celebrity pals that includes American Idol judge Simon Cowell. He spends his weekends in a Monaco penthouse apartment or on the Lionheart, his 164-foot luxury yacht, and uses a private Gulfstream jet to shuttle between London and the French Riviera. Today, the kid from the drab south London suburb of Croydon has the cash to hire Beyoncé to sing at his son’s 2005 bar mitzvah—and the chutzpah to try to conquer the American retail market.

“Green’s New York store is a statement of his intent that Topshop will become a global fashion brand,” says Greg Hodge, an analyst at London-based industry research firm Planet Retail Ltd.

Munching a blueberry muffin in the cafeteria of Bhs’s Oxford Street store, Green says Topshop is ready to take on its multiple competitors in the US. One rival: Stockholm, Sweden-based Hennes & Mauritz AB, known as H&M, which opened its first New York outlet in 2000. H&M now has 175 stores across the US. The group’s total US sales in local currency fell 5 percent to $789 million in the nine months to August 31.

Green is trying to succeed in a US market that has brought down bigger British rivals, including Marks & Spencer Group Plc., Britain’s No. 1 clothes retailer and the target of two Green takeover attempts. The risk is that Green’s single New York outlet won’t generate enough buzz—or revenue—to compete with the more-established rivals such as H&M.

In 1988, M&S bought Brooks Brothers Inc., the New York men’s store established in 1818 that has clothed generations of US bankers and lawyers, for $750 million. The UK retailer foundered as it tampered with Brooks Brothers’ conservative stylings and sold the venerable clothier for a fire sale price of $225 million in 2001.

To succeed in the fickle world of young women’s fashion, retailers must combine glamour with speed to deliver fast fashion.

“Topshop is bringing new merchandise into its SoHo store every four to six weeks, and because Green has knocked out so many middlemen, he’s able to deliver the clothes at a more affordable price,” says Kathryn Deane, president of Tobe, a fashion research firm in New York. That means New York teens can get their hands on suede culottes from Moss’s collection for $170 soon after they spot her wearing them in the pages of fashion magazines. Some “Limited Edition” items from the Moss collection can’t be returned to the shop for a refund.

Green says he’s always ready to grab a good deal. “We could do a deal this afternoon for $1 billion without any stress,” says Green, who does business on two Nokia mobile phones—one exclusively for incoming calls and the other for his outgoing conversations.

In New York, Green has replicated popular features such as free in-house style advisers found in Topshop’s flagship Oxford Street store to lure fashion-crazy teenagers. And then there’s Moss, who also hails from Croydon.

In 2005, a London tabloid published a front-page photo of the supermodel purportedly snorting cocaine. In the wake of the scandal, in which she was dubbed “Cocaine Kate,” Moss lost contracts with companies such as Burberry Group Plc., Chanel SA and H&M. Police questioned her over the incident but didn’t bring any charges.

The following year, Green hired her to lend her name to a Topshop designer collection. Since then, Moss, 35, has returned to fashion’s A-list-often appearing with her patron Green at her side.

“She needed somebody at that moment, and I felt I could manage her,” Green said in late September over a lunch of poached salmon at Arcadia’s head office.

Green’s incoming mobile phone rings. It’s Moss, wanting advice about what to wear for the 50th birthday party Green is hosting in two days for his friend Cowell.

“Hello; we’ve just been talking about you,” Green says as he saunters out of the sixth-floor meeting room to discuss Moss’s wardrobe conundrum in private.

For all of his jet setting, the heart of Green’s business empire is still central London’s retail district around Oxford Street, where he started out in the rag trade.

Green’s father, Simon, who died when Green was 12, ran several electronics shops, while his mother, Alma, operated self-service gas stations. In 1968, Green quit Carmel College, a private boarding school for Jewish boys in rural Oxfordshire, before receiving the equivalent of a high-school diploma.

He then got a job with a shoe importer in London, and in the 1970s became a middleman, buying clothes from wholesalers and selling to UK retail chains. In 1981, he opened Bond Street Bandit, where he sold liquidated stock from designers such as Giorgio Armani SpA and Hugo Boss AG and flogged the out-of-date fashion in his shop.

His first big step up the rag trade ladder came in the mid-1980s, when he bought Jean Jeanie, a debt-ridden denim retail chain based in Slough, England, for £65,000. In just a few months, he slashed costs by cutting deals directly with Asian manufacturers. In 1986, Green sold Jean Jeanie to UK competitor Lee Cooper Jeans for £7 million.

In 1988, Green became chief executive officer of Amber Day Holdings Plc., a publicly traded fashion retail group in London, after buying 16 percent of the company. He resigned in September 1992 when Amber Day reported annual profit of £7.5 million, a 26-percent fall from a year earlier. Green had forecast that profit would rise. In April 1993, Green sold his Amber Day stake for about £7.7 million.

That cash propelled another round of dealmaking. In 1995, Tom Hunter, a Scottish retail entrepreneur, asked Green for help in buying Olympus Sports, a designer sporting goods company. Olympus competed with Hunter’s Sports Division stores and was owned by Sears Plc., a London-based shoes and department store group.

Sears—which wasn’t affiliated with the US retailer—rejected the then 34-year-old Hunter’s first bid because he seemed too young to be serious, the Scot says. Green stepped in to lead the negotiations, and in November 1995 Hunter bought Olympus for £25 million.

As Green negotiated the reward for the Olympus deal, his lawyer kept interrupting him, Hunter recalls.

“The lawyer said, ‘Philip, I know what you’re going to say.’ And Philip—in his usual style—said, ‘I don’t know what I’m going to say, so how the f— do you?’” In return, Green got a 13-percent stake in Sports Division, which now included Olympus, and became the company’s chairman.

Three years later, Green assembled a consortium to buy the rest of Sears with a group that included twin-brother real-estate investors David and Frederick Barclay. Green pledged as much as £20 million of his own cash, while Edinburgh-based Bank of Scotland Plc. helped organize a credit line for the £548-million deal completed in January 1999. As Sears CEO, Green sold off all of the company’s holdings to competitors, including then-rival Arcadia, for about £800 million.

Flush with cash, Green looked around for another retail acquisition—and set his sights on the biggest clothing retailer in the UK.

In 1999, Green approached Marks & Spencer about making a bid. After the M&S board rebuffed him, he targeted department store chain Bhs, which he bought in 2000 for £200 million. In 2002, he acquired Arcadia, the owner of Topshop, for £850 million.

Investors looking to buy into Green’s businesses are out of luck. After Amber Day, Green vowed never to work again for a publicly traded retailer that needed to please investors every quarter. When Green sets out to buy a stock-market-listed business, shareholders sometimes benefit because of the premium he’s willing to pay. The price he paid for Arcadia was 36 percent higher than the shares were worth when he announced his bid.

Those earlier deals were peanuts compared with Green’s hostile £9.1-billion bid for Marks & Spencer in July 2004, including £1.6 billion of his own cash. The offer valued the company at about 40 percent more than its share price at the time.

Green’s bid hit trouble when Stuart Rose, Arcadia’s former CEO and part of Green’s prospective Marks & Spencer management team, defected to the enemy to become Marks & Spencer CEO in May 2004.

Four days after Rose’s appointment, Green was walking past M&S’s head office on London’s Baker Street when he spotted Rose’s car.

“I opened the car door and his driver went this color,” he says, pointing at his white shirt. “So I said, ‘I thought you wanted to be an owner?’ Stuart said, ‘We both couldn’t be boss.’” The following month, Rose persuaded M&S shareholders to reject Green’s offer.

In 2006, Green was knighted for services to the retail industry by Queen Elizabeth II and is now known as Sir Philip. His wife, Tina; son, Brandon; and daughter, Chloe, live in Monaco. Green still drops by Marks & Spencer’s stores to monitor displays and foot traffic, and he says he’s patched things up with Rose. In March, Green organized a joint birthday party for himself and Rose at Annabel’s, a London nightclub, with Diana Ross as the surprise performer.

“One of the reasons I get on with Philip Green so well is the fact that I don’t work for him,” Rose says.

Green has a habit of hiring stars for his private entertainment. Ricky Martin and George Michael performed at his 55th birthday party in the Maldives, while Paul Anka sang at his mother’s 90th in London in 2008.

In June, Green announced a possible television entertainment joint venture with his friend Cowell. Green told students at London’s Fashion Retail Academy last month that he planned to help Cowell transform the talent shows into global merchandising brands. Cowell could not be reached for comment.

Green says Topshop’s US outlet will be profitable in its first year thanks in part to his retailing flair.

“If you’ve got my feely-touchy, I think America’s our sort of market,” he says, rubbing his index finger and thumb together.

The instincts that have served the Bond Street Bandit on his home turf will have to make the transfer to Broadway—and beyond.