NEW YORK, United States — 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 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.

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, Chief Executive Officer 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.”

Yet some experts say that the high-end route may not be right path for Bezos and his e-commerce empire. “It’s a prize that everybody would love to get. The idea is that if luxury brands will work with you, everyone else would fall in line,” said Forrester Research analyst Sucharita Mulpuru. The problem? “The luxury fashion world isn’t even that large from a revenue standpoint with respect to the rest of the apparel world.” For instance, Saks Fifth Avenue and Neiman Marcus combined brought in less than $10 billion sales in 2013. “There seems to be an obsession with getting to $200 billion in sales, which is the main reason Amazon is obsessed with clothing and grocery. That’s where the size is,” says Mulpuru. “The irony is that, to get that number, you don’t even need [to capture] the high end.”

More basic apparel, rather than high-end couture, may be the better bet. Amazon said in 2013 that 35 million of its active customers were shopping for clothes— making it the site’s fastest growing category. About 6 percent of purchases on Amazon are clothing and accessories, according to San Francisco-based Slice Intelligence, which measures online shopping. That makes clothing Amazon’s fourth-largest category, ahead of books and behind electronics, home and kitchen, and health and beauty. But clothing and fashion are two different things. Only 16 of the 100 top global prestige brands officially sell on Amazon, according to business intelligence firm L2. The company clearly wants to change that, but hiring a former Vogue editor and sponsoring a high-profile fashion show aren't yet enough. “The truth is, Amazon is not Neiman Marcus," says Mulpuru, "and the consumer recognizes that.”

By: Kim Bhasin and Lauren Sherman; editor: Katie Drummond.