Can Entrepreneurs Really Wear What They Want? You may be your own boss, but that doesn't mean you should pull a Mark Zuckerberg and wear hoodies to investor meetings. Here's some advice.

David Simnick had been on a roll raising as much as $150,000 in capital at investor meetings while sporting a casual look of jeans, untucked button-down shirts and boat shoes.

The 25-year-old co-founder of SoapBox Soaps had a go-to wardrobe which he describes as "par for the course." Dan Doll, his business partner, dressed similarly.

But one day last fall, both men were done in by their denim.

Seeking more than $100,000 in funding from a larger investment source, Simnick and Doll strolled into the meeting wearing their customary relaxed garb. After the presentation, while driving home, they got a phone call from their mentor who had been at the session.

"It was a 'What were you thinking!' type of call," says Simnick, who had always believed that if you dressed up too fiercely when seeking cash, the other side might smell desperation. "Our mentor told us, specifically because of our attire, that we had come off as being unpolished and had made a terrible impression on the middle-aged investor who, as it turned out, never followed up."

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Simnick and Doll decided on the spot they'd never make the same mistake again. "Whole Foods is a flip-flops type of meeting, small-chain supermarkets are a khakis meeting, and tier-one companies and national supermarket chains are suit-and-tie meetings," says Simnick. "We've really learned to match how we dress with who we're going to be speaking with."

What fuels most people to start their own business is the thrill of creating a new product or service, the sky's-the-limit financial aspirations, the satisfaction of running one's own show. But somewhere in that list, isn't there the added perk of limitless self-expression, particularly in terms of wardrobe? After all, being sartorially oneself didn't hurt hoodie-headed Mark Zuckerberg, did it?

Not so fast, experts say.

"Over the last decade, the workplace and meetings have become a lot more relaxed and informal," says Patty Buccellato, a certified image professional based in Rochester Hills, Mich. "The downside, though, is that many entrepreneurs have stopped making exceptions to this routinely casual style, especially when they're seeking funding. Unfortunately, these miscalculations often don't register until people get negative feedback and the damage has already been done."

While no entrepreneurs want to feel they have to put on a costume as a condition for doing business, experts suggest there's an easily navigable middle ground.

1. Dress for the occasion. Buccellato describes one client with a high profile within his organization, and who typically wore khaki trousers and short-sleeved knit polo shirts while walking the floor of the production facility. "Because this was his typical attire, he didn't think twice about wearing it to a video-taping session related to a YouTube posting for his company," she says. Upper management became aware of the gaffe – that his wardrobe did not align with an ideal presentation of the brand – only after the fact.

"Most entrepreneurs emphasize efficiency and tasks," she says. "Often they don't consider visual presentation which, to be effective, needs to be customized according to interactions with different people or in varied situations."

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2. Don't copycat. Michèle Benza, an image consultant in San Francisco who has a large Silicon Valley clientele, describes one female entrepreneur who knew her formal, drab way of dressing at new-business meetings was the likely reason she wasn't winning clients. "This person came to me, wanting to model her new look after a high-profile television personality, which I knew was not a good match for her," says Benza. "In general, it's better not to copycat but rather to find your own personal style."

For people without the budget to hire an image consultant, Benza suggests finding retail-clothing salespeople you can trust to help you achieve your new look, based on your daily business agenda, meetings and travel. "This search may take some legwork," she says.

3. Practice wearing new clothing. Whether you've decided to experiment with a more dressed up or dressed down style, your new look will likely feel strange at first. "There's nothing worse than being uncomfortable or feeling awkward in your clothes at an important meeting, so you literally may have to practice wearing these garments at home," says Benza.

If this sounds like a dress rehearsal, that's exactly what it is. "You need to wear the entire outfit, including shoes and accessories," she says, noting that it may take as many as dozen test runs before your attire feels like second skin.

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4. Color brand appropriately. Brandon Evans, founder and CEO of Crowdtap, a social-influence marketing platform based in New York City, wears red converse sneakers to all his speaking engagements. "This footwear really sticks out, gives attendees an easy way to spot me during the rest of the event, and makes more of a statement than a suit and tie would," he says, noting that red is also the color that represents the Crowdtap brand.

For Evans, it's less about casual vs. formal attire, and more about being authentic but also knowing your audience. "If you're a genius programmer, you can probably get away with wearing a T-shirt and looking a bit disheveled," he says. "But if your role involves sales and presentations, the audience's expectation may be different."

5. When in doubt, play it safe. Although many entrepreneurs like to present themselves in a "what you see is what you get" style, sometimes being your idiosyncratic self is, well, too much idiosyncrasy. "Ask yourself: Who am I talking to and why," says Buccellato. "And, when in doubt, self-expression is often best reserved for one's personal life."

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