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In 1968, Klein founded Calvin Klein Limited, a coat shop in the York Hotel in New York City, with $10,000. Legend has it that a year later a buyer from Bonwit Teller got off the elevator on the wrong floor, and ended up placing a $50,000 order. It is more likely though, that Klein showed his work to Bonwit Teller staff, which led to the first Calvin Klein collection: a line of men's and women's coats featured at the New York City store.

In 1969, Mr. Klein, who was later described as "the supreme master of minimalism," appeared on the cover of Vogue magazine. By 1971, sportswear, classic blazers as well as lingerie were added to his women's collection. In 1973, he was awarded the Coty Award for the first time, which he received for three consecutive years, for his 74-piece womenswear collection. By 1977, annual revenues had jumped up to $30 million, and he had licenses for scarves, shoes, belts, furs, sunglasses, and sheets. Klein and Schwartz were making $4 million each. After the company signed licenses for cosmetics, jeans, and menswear, Klein's annual retail volume was estimated at $100 million. In 1978, Klein claimed sales of 200,000 pairs of his famous jeans the first week they were on the market. By 1981, Fortune magazine figured Klein's annual income at $8.5 million a year. In the mid-1970s, he had created a designer-jeans craze by putting his name on the back pocket. The jeans were famously advertised with a commercial featuring a 15-year-old Brooke Shields cooing in 1979/80 that "nothing comes between me and my Calvins" and "I've got seven Calvins in my closet, and if they could talk, I'd be ruined." Controversial advertising, including a series of ads featuring adolescents in sexually evocative poses, has been a recurring theme for the company. Shields advertised for Klein underwear in 1984 as well.

In the late 1970s, the company also made attempts to set up its own fragrance and cosmetics business, but soon withdrew from the market with big financial losses. In the 1980s, as the designer-jeans frenzy reached its all-time high, Calvin Klein introduced a highly successful line of boxer shorts for women and a men’s underwear collection which would later gross $70 million in a single year. Calvin Klein’s underwear business, promoted later in the 1990s with giant billboards showing images of pop singer "Marky Mark" Mark Wahlberg, was so successful that his underpants became generally known as "Calvins".

The stunning growth continued through the early eighties. The licensing program, which brought in $24,000 when it was initiated in 1974, had royalty income of $7.3 million ten years later. That year, worldwide retail sales were estimated at more than $600 million. Klein's clothes were sold through 12,000 stores in the United States and were available in six other countries. His annual income passed $12 million.

Financial problems, increased pressure from all sides, disagreements with the licensee of the menswear line and its disappointing sales as well as an enormous employee turnover both within Calvin Klein and its licensing partners led to the first rumors that Calvin Klein Industries, as the company had been known by then, was up for sale. And indeed, in late 1987, it was said that the sale of the company to Triangle Industries, a container manufacturer, had only failed because of the crashing stock market.

Although the company almost faced bankruptcy in 1992, Calvin Klein managed to regain and increase the profitability of his empire throughout the later 90s, mainly through the success of its highly popular underwear and fragrance lines, as well as the ck sportswear line. Mr. Klein was named "America's Best Designer" for his minimalist all-American designs in 1993, and it came as a surprise in 1999 when it was announced that CKI was again up for sale. Planning to expand its business, the company had been approached by two luxury goods companies, LVMH and Pinault Printemps Redoute, to join Calvin Klein, but nothing resulted. Other potentials like Tommy Hilfiger Corp. and Italy's Holding di Partecipazioni proved to be similar disappointments because of CKI's steep price tag of supposedly $1 billion. After seven months and no potential buyer, Mr. Klein announced that his empire was not on the market any more. The company would never manage to go public, which had supposedly been Mr. Klein's plan once. In June 2008, Calvin Klein started to sponsor America's Next Top Male Model, allowing the winner to embark on a 100,000 dollar contract as well as a runway show, as a bonus, to launch their career.

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review by . December 17, 2008
Calvin Klein Underwear show
When I'm shopping for a bra, I usually don't listen to the saleslady's advice on support structures or whatnot. I just want it to look good. I want it to be something I can wear day and night, and not worry about whether or not the underwire is jutting out or not. If there's lace, I don't want the lace pattern imprinting through my shirt.  The first brand I look at is Calvin Klein. I like my lady undergarments to look modern and sleek. A bit of lace, no frills. I like smooth microfibers and artsy …
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