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Fashion Victim: Snapchat Founder Evan Spiegel Mugs in Bizarre Photoshoot for Italian Vogue Here's what not to do when you're a 25-year-old billionaire.

By Geoff Weiss

Opinions expressed by Entrepreneur contributors are their own.

In recent years, the well-worn path from fashion icon to entrepreneur has been tread -- to varying degrees of success -- by the likes of Jessica Simpson, Kanye West, the Kardashian clan and many more.

But now, it's beginning to look like something of a two-way street.

Most recently, for instance, 25-year-old Snapchat founder Evan Spiegel struck a sultry pose on the cover of L'Uomo Vogue, the Italian men's edition of the famed fashion bible. The spread inside marks a dashing departure from the relatively homely images hewn by fellow founders today.

While Mark Zuckerberg has proclaimed the virtue of hoodies and plain grey T-shirts, here is Spiegel, pouting in a Louis Vuitton biker jacket. Imagine Steve Jobs -- who turned mock turtlenecks and orthopedic sneakers into an iconic uniform of sorts -- mugging with a puppy and bedecked in Burberry.

Related: 5 Facts About Evan Spiegel, Snapchat's Often Controversial Co-Founder

Unsurprisingly, the response to Spiegel's shoot thus far has been fairly contentious. While GQ debated whether Spiegel was Silicon Valley's first sex symbol, other media types quipped that the shoot typified the startup sphere's bizarre bravado, wishing that the cringe-worthy photos would simply disappear.

This smacks of a similar hullabaloo in 2013, when Yahoo CEO Marissa Mayer appeared in the September issue of Vogue, sprawled on a chaise lounge wearing Michael Kors and holding an iPad with her face onscreen. At the time, brand strategists called the move an attempt to heighten Yahoo's "coolness quotient," but condemned Mayer's pose as too flippant.

Though Spiegel's reputation as a fratty chauvinist with a supermodel girlfriend and a penchant for uber-expensive cars probably doesn't help, his latest pose shows that when founders try to make their mark on the elitist and frivolous world of high fashion, it's rarely a good look.

Related: Should Marissa Mayer Have Posed in Vogue?

Geoff Weiss

Staff Writer. Frequently covers digital media.

Geoff Weiss is a staff writer at Entrepreneur.com who frequently covers digital media.

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