Three of the company's fashion sites—Amazon Fashion, East Dane and MyHabit—will sponsor a menswear version of Fashion Week in New York as Amazon.com continues its push to enter the designer clothing world.

(Bloomberg Business)—For the first time, a menswear version of Fashion Week will come to New York this summer. Bulbs will flash as photographers hustle to document the best looks from the spectacle’s dapper attendees.

Designer labels such as Calvin Klein, Michael Kors, and Rag & Bone will showcase their most creative garments on radiant catwalks. And plastered on it all will be the name of an unlikely retailer: Amazon. Three of the company’s fashion sites—Amazon Fashion, East Dane and MyHabit—will sponsor the event, the Council of Fashion Designers of America announced earlier this month.

Amazon.com Inc., No. 1 in the Internet Retailer Top 500 Guide has, in recent years, pushed to enter the world of designer fashion, selling clothing, shoes, handbags, and accessories from pricey brands with luxe reputations. Amazon reportedly also signed a multiyear deal last week to sponsor India Fashion Week, according to Women’s Wear Daily.

Over the past four years, the company has hired Barneys New York fashion director Julie Gilhart as an adviser, sponsored the 2012 Met Gala, and opened a 40,000-square-foot photography studio in Brooklyn. (The company plans to open an even bigger one in London.) And Amazon hosts events for students from such leading fashion schools as the Fashion Institute of Technology and Parsons the New School for Design.

Integral to this effort is Amazon Fashion, a section of the main website that sells well-known brands in what’s known as the “contemporary” category— designer labels that don’t carry the astronomical price tags of luxury fashion houses like Chanel and Prada. On the site, women can buy $500 satchels from Zac Posen or $200 pumps from Badgeley Mischka. For men, there are $300 oxfords from Hugo Boss and $700 overcoats from Theory. The site launched its first TV ad campaign in 2013, looking to persuade shoppers that it can be relied on as a source for swanky merchandise. This month, Amazon hired Vogue editor Caroline Palmer to head up editorial duties at the site. Amazon has also pushed websites Shopbop and Zappos, which it acquired in 2006 and 2009, respectively, toward a higher-end aesthetic. Shopbop has brought in famous designer labels, including Thakoon and Wes Gordon, and started running ads in Vogue. Zappos’s high-end offshoot, called Zappos Couture, brought in fashion icon Andre Leon Talley in 2013 as artistic director and attracted brands such as Red Valentino and Vivienne Westwood Gold Label. The Talley experiment ended in late 2014, but Amazon’s fervent desire for more affluent clothing customers is clear.

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Industry observers say it’s difficult to insert couture items under the Amazon banner, which has long thrived on offering a practical, easy way to buy just about anything. Fashion, on the other hand, is often impractical, dominated by unpredictable trends and personal taste. Where Amazon is known for being a massive vending machine, fashion is carefully curated. “What’s missing—what can be improved upon—is that there is theater involved in fashion,” says Ari Bloom, founder of New York-based A2B Ventures, a strategic advisory firm that works in fashion, food, and wellness. “Amazon’s brand positioning has really been about convenience and price. Fashion is often about experience.”

A representative for Amazon declined to comment for this article. But in an interview with the New York Times in 2012, CEO Jeff Bezos said the company’s initial move toward luxury was spurred by simple economics because “gross profit dollars per unit will be much higher on a fashion item,” compared with cheaper products. In his 2013 book, “The Everything Store: Jeff Bezos and the Age of Amazon,” Bloomberg Businessweek writer Brad Stone quotes Bezos as frequently saying, “In order to be a two-hundred-billion-dollar company, we’ve got to learn how to sell clothes and food.”

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