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Entrepreneur Makeover: From Geek-in-Chief to Head Hottie

5 min read

This story appears in the March 2011 issue of . Subscribe »

Randall Weidberg, founder and CEO of
Photography by Natalie Brasington

If, while watching The Social Network, you were either not horrified by or--shudder--gave a thumbs up to Mark Zuckerberg's shower sandals style, this article is for you. (If you wore shower sandals to the movie theater, this article is really for you.)

Flipping through back issues of Entrepreneur, we noticed that budding business moguls consistently make some prominent fashion faux pas.

What did we see? Open dress shirts over graphic-emblazoned T-shirts. Wrinkled slacks paired with hiking boots. Dirty sneakers that Goodwill workers would reject. And, sigh, a continuing love affair with really thick early-'90s neckties and Matrix-ready all-black ensembles.

To give you an idea of how to amp up your own style (and business), we asked Los Angeles celebrity stylist Monica Schweiger to put her taste to work for one up-and-coming entrepreneur. Schweiger has had a hand in dressing style icons including Anderson Cooper, P. Diddy and musician Mayer Hawthorne.

Entrepreneur Makeover: A Nerd Gets a New Look

Schweiger's challenge: turn Randall Weidberg, founder and CEO of Boulder, Colo.-based social shopping website, from chief nerd to something far (far) hipper--without pushing his personality out of the picture. This, in spite of the fact that Weidberg didn't think a makeover was a must for his life or business.

Click to see our before and after makeover results.

"At the end of the day, you're thinking about your company and what you need to do to make it grow," he says. "It isn't really about what you're wearing."

True. But lack of attention to your duds can detract from your business message. Would you rather potential investors pay attention to your wrinkled tee or to your bold idea? An entrepreneur is also the public face of the company. Since launching his outdoor enthusiast-focused e-commerce company last year, Weidberg has attended countless meetings, spoken on plenty of industry and tech panels and, yes, he has even appeared on

We sent Weidberg to meet Schweiger at Ever, a decidedly cool L.A. shop. There, the stylist kicked off the entrepreneur's education on the art of modern business-casual style.

"When it comes to a business outfit, it really depends on the occasion," she says. Case in point: You don't want to wear the same thing you'd sport to a coffeehouse get-together with your graphic designer to a formal boardroom meeting with a venture capitalist.

But if you insist on pushing the boundaries of business dress, we beg of you: Learn how to iron (or, better yet, find a good dry cleaner).

Schweiger suggests buying structured jeans in a natural to dark wash. A good pair of jeans is a versatile friend. Combine them with sneakers and a polo shirt for casual days or desert boots and a sport coat for meetings.

Schweiger replaced Weidberg's khakis with a pair of Ever's coated black Maywood jeans ($198), which, she says, can easily be dressed up or down.

"I love these," Weidberg says, admiring the pants. "They definitely look different than what my programmers would wear."

Of course, there are times when something dressier is in order. "It doesn't hurt to invest in at least one tailored suit that actually fits," Schweiger says.

If you're living on a startup king's budget, she suggests going to a vintage store or resale shop where gently used designer suiting can usually be found for a lot less than retail. "Also, H&M is great for inexpensive and shockingly well-fitting men's suits," she says. Then, have that suit tailored.

Piece by piece, Schweiger fixed some of our entrepreneur's most glaring crimes of fashion. Then she took him to Gavert Atelier salon in Beverly Hills for a quick cleanup. Stylist Mika Fowler, who counts Glee cast members as clients, didn't even bust out her scissors for Weidberg's shaggy mane. She says a full-on cut is unnecessary if the goal is a polished look for meetings and speaking engagements. "Product is the most important thing," she says.

For Weidberg's longish hair, Fowler used liberal amounts of Joico's Design Collection Flexible Shaping Spray and Humidity Blocker to achieve a shiny, natural, stay-put look. Total time for the coiffing process? Five minutes. "You don't have to spend a lot of time to look put together," Schweiger says.

Really, she adds, style is just about "paying attention to the details." Swap the boring businessman leather shoes for retro sneakers. Trade out the graphic T-shirt under your open button-down for a solid color. Make sure things match. But don't take your outfit too seriously.

"And look in a mirror before you leave the house," Schweiger says. "That's usually the biggest help of all."

See our makeover results below. Click on the images for details and descriptions.

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