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Bluefly was founded in 1998 by Ken Seiff and Jonathan Morris. The website opened for business on September 8, 1998, offering items from 40 designers, including apparel from such well-known brands as Ralph Lauren, Tommy Hilfiger, J. Crew, and Donna Karan. In that first month, the company shipped 96 orders, but just three months later, in December, Bluefly shipped more than 2,700 orders. Traffic to the site also increased rapidly, growing from 28,000 unique visitors to some 660,000. Registered users also grew from 1,572 at the end of September to 26,048 at the end of 1998. The company also established an alliance with the Yahoo shopping site, creating a co-branded store that resulted in a 40 percent increase in the price of Bluefly stock. In addition, Bluefly also established a strategic marketing deal with another prominent Internet portal, Lycos.[1]

In 1999, Bluefly raised $10 million from Peter Lynch and George Soros.[2] That same year Bluefly became an anchor tenant in America Online's shopping channel.[3] To build its brand awareness, Bluefly ran a series of advertisements in prominent fashion magazines such as Vogue and Elle.[4]