Calvin Klein Collection Cream and Black Circle Pleat Sleeveless Shift Dress

Known for his minimalist, comfortable womenswear as well as a range of sexually provocative ad campaigns that continue to generate conversation decades later, Calvin Klein initially experienced the garment industry as a child in his grandmother’s New York City tailoring business. He would one day establish a global fashion brand — the Bronx native led the designer jeans craze of the late 1970s, and vintage Calvin Klein skirts, jackets, day dresses and shirts, frequently created in soft fabrics and understated neutral hues, are still versatile components of everyday wear.

Klein was born in 1942. He joined his mother on trips to designer discount store Loehmann’s and visited his grandmother's seamstress shop, where he was able to witness the particulars of clothing design in his youth. As a teen, Klein started making fashion sketches and attended the High School of Art and Design and the Art Students League of New York. He graduated from the Fashion Institute of Technology in 1963.

Klein worked with coat manufacturer Dan Millstein after his studies had concluded. In 1968, he partnered with his childhood friend, Barry Schwartz, and opened a small coat and dress shop in the York Hotel in Manhattan. Schwartz ran the business side of things while Klein took the reins on creative direction. The designer’s work was soon stocked at Bonwit Teller — and appeared in large ads in the New York Times — and in 1969, a model sported a Calvin Klein coat on the cover of Vogue.

During the 1970s, Klein added sportswear, lingerie, blazers and a range of stylish accessories to his lines of apparel. He became the youngest-ever recipient of the Coty American Fashion Critics' Award in 1973, winning again in both of the subsequent two years. 

Klein’s debut of his now-revered blue jeans in 1976 was somewhat of a failure — they were too expensive, and buyers complained about the fit. Late one night at Studio 54, the designer heard about the benefits that a licensing deal with apparel manufacturer Puritan Fashions might bring him. Two years later, Klein inked that deal and sold 200,000 pairs of his jeans, which were produced by Puritan, in a week.

A large percentage of Puritan’s sales in 1978 owed to Klein’s blue jeans. This streak with denim carried on into the 1980s, when Klein would be competing with the likes of Jordache, Gloria Vanderbilt and other labels. Klein’s jeans were promoted in scandalous ads featuring Brooke Shields and others that were banned by television stations and challenged by politicians. The decade saw the debut of successful men's and women's underwear collections designed by Klein that were also the subjects of steamy marketing campaigns. Soon, Calvin Klein expanded to 12,000 American stores and retail locations in six other countries.

Though profits declined in the early 1990s, Klein saved the business with successful underwear, sportswear and fragrance lines. More controversial ad campaigns with up-and-coming models and celebrities like Kate Moss and Mark Wahlberg followed, also bringing fresh attention to the brand. In 2002, the Calvin Klein company was sold to Phillips Van Heusen Corp. Belgian designer Raf Simons was named chief creative officer at the brand in 2016.

On 1stDibs, find vintage Calvin Klein clothing, accessories and handbags.