Calvin Klein from an early age aspired to be a fashion designer. After growing up in the borough of the Bronx in New York City, Calvin Klein went to study at the Fashion Institute of Technology. He graduated in 1963 and went to work in Manhattan's garment district for a women's coat and suit manufacturer before he was able to open his own business in 1968 after receiving a $10,000 loan from his childhood friend, Barry Schwartz, who then joined the business shortly after. The business had humble beginnings with Calvin Klein renting a small and run-down studio to exhibit his first line of samples that concentrated on men and women's coats. As legend has it one of the vice-presidents from Bonwit Teller accidentally got out of the lift on the wrong floor of the building and walked straight into Calvin Klein's showroom. He was immediately impressed by what he saw, and set up a meeting with Klein and the company's president, who subsequently placed an order to the value of $50,000 retail. It provided huge exposure for the new label and was a massive break for Calvin Klein who then went on to book $1 million worth of sales in his very first year of business. By 1971 this figure had reached $5 million and by 1977 Calvin Klein's sales had risen to an astonishing $90 million.

Calvin Klein quickly became renowned for his use of simple lines, classic fabrics, and restrained use of colour, a signature that saw him described later as "the supreme master of minimalism". In 1973 Calvin Klein won fashion's equivalent of the Oscar, a Coty American Fashion Critics Award, which he went on to receive for an unprecedented three years in a row. At the tender age of 32, Calvin Klein was inducted into the group's Hall of Fame.

In 1971, sportswear and lingerie were added to his women's portfolio and by 1977 the Calvin Klein name was printed on sunglasses, leather goods (including shoes and belts) and homewares. The company then quickly expanded into a keenly awaited menswear line as well as cosmetics and jeans. The Calvin Klein denim line was such a success that by 1978 it was claimed that over 200,000 pairs were sold within the first week of their being released. The success continued throughout the 1980's and was accompanied by controversial advertising, most famously a 1979 series of television commercials directed by Richard Avedon and featuring a 15-year-old Brook Shields posing provocatively in a skin-tight pair of Calvin Klein jeans purring "Do you know what comes between me and my Calvins? Nothing." and "I've got seven Calvins in my closet, and if they could talk, I'd be ruined". The depiction of adolescent sexuality struck a nerve and a huge public outcry followed causing the major American television networks to ban the two commercials from the air. However the complaints didn't affect his jeans sales, which were growing rapidly to nearly two million pairs per month. Another Calvin Klein Jeans advertising campaign featuring model Patti Hansen on her hands and knees caused a huge sensation when it was plastered all over a Times Square billboard and the company subsequently decided to keep the advertising campaign in place for the next four years. When Calvin Klein had claimed one-fifth of the world's jeans market, a company spokesman observed, "the tighter they are, the better they sell". Since then Calvin Klein has built his empire upon iconic advertising campaigns featuring top models such as Kate Moss, Christy Turlington, Lara Stone, Gemma Ward and Natalia Vodianova, and celebrities such as Mark Wahlberg, Scarlett Johansson and Eva Mendes. His famous advertising campaigns have been shown across the globe, spanning 21 countries and reaching a global audience estimated at 98 million. Calvin Klein advertising has been photographed by some of the world's most famous photographers including Bruce Weber, Richard Avedon, Mario Sorrenti, David Sims, Steven Meisel and Steven Klein.

Calvin Kleins most sought-after product has been his highly successful fragrance line and once again he took advantage of high profile and controversial advertising to help launch his new products. In 1985 Calvin Klein launched Obsession and spent more than $23 million creating highly memorable television and print advertising campaigns for the men and women's line. In one campaign shot by Mario Sorrenti, a very young Kate Moss lay naked on a couch staring wide-eyed into the camera, while in another shot by Bruce Weber, a series of print advertising show three naked and entangled women in one, two naked men lay entwined around a young girl in another one, and the third depicts a naked couple pressed together. By 1987 Calvin Klein's Obsession had reached over $100 million in sales and had become the second-best selling perfume in the world. In 1988 Calvin Klein launched Eternity and with its release came another expensive advertising campaign. However this time around, inspired by his recent marriage to his second wife, Calvin Klein stayed away from the allure of youth and sex and instead concentrated on the themes of love, commitment and spirituality. Eternity was followed by Escape and Escape for Men, which proved to be another success for Calvin Klein. Nothing however could have prepared them for what was to come when they launched CK One in 1994. The unisex fragrance became a massive success and within its first three months had reached sales of over $60 million. It took the fragrance market in a completely different direction and all of a sudden unisex fragrances were being developed around the world. In 1996 a black and white print and television campaign directed by legendary photographer Richard Avedon helped launch CK Be, another installment of his unisex fragrance line. The campaign saw a pose of pierced and tattooed models that didn't appeal to the majority of the population. However it did seem to resonate for teenagers, amazingly the exact market that was buying the product. Calvin Klein advertising and controversy seemed to have stayed close together. He did after all launch the career of a very young and skinny Kate Moss, which in turn launched the new 'heroine-chic' look that became the target of anti-anorexia campaigners. For the first time Calvin Klein was deemed to have gone too far with a 1995 campaign for CK Jeans featuring teenagers that "suggested auditions for low-budget porn movies". For the first time after years of controversial advertising and public outcry, Calvin Klein had to cancel the campaign, and a US Justice Department investigation ensued, however no charges were laid after it was determined that under-age models were not used.

After introducing men and women's underwear into his already cramped portfolio in 1982, Calvin Klein once again exploited youth and sex with a series of advertising campaigns photographed by Bruce Weber and featuring Brazilian Olympic pole vaulter Tom Hintnaus. After Calvin Klein rented advertising space in 25 New York bus shelters to display the campaign, all 25 posters had been stolen by the first night. The company jumped on the success and quickly produced a women's underwear line of male-style briefs and boxer shorts that all featured the fly front. In the early 1990's Calvin Klein enlisted the then pop-singer Marky Mark (Mark Wahlberg) to promote the Men's Underwear line. Billboards depicting a very buff Marky Mark in Calvin Klein underwear were splashed across America and were hugely successful. The images have since become iconic. "Calvins" as they became generally known turned into one of the most famous Men's underwear lines in the world and would forever change the way men would think about and buy underwear. They turned from being simply a functional object into a sought-after and fashion-forward product, leading the market with cutting-edge designs, innovative fabrics, and exceptional fit and quality to which they have become famous. The men's line features fabrics that range from natural cottons to sheer synthetics, while the women's line features sexy lace and satin details as well as fashion-forward prints and styles. Each season Calvin Klein Underwear also produces an updated basics line using current colour palettes and modernized fabrics using the latest technology.