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Red, White and Fabulous? Fashion Tips from the Campaign Trail

October 26, 2012
URL: http://www.entrepreneur.com/article/224777
Power Suit

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Power Suit

Jenkins and Hunter: “The President, as he should, has a powerful look. The suits always fit well, and his appearance is always well-kempt. The knot of his tie could use a little TLC -- it’s slightly on the large side -- but it’s still a power tie. If only we could get him to give up those black suits.”

Vidisheva: “The dark tie makes Obama look too unfriendly. Perhaps in old times, you needed to dress up to show that you are in power, but for me, your achievements should speak for themselves."

Leroy: “Too dour. For such a slim and handsome guy, he should add more color in his shirts and ties. He’s the president -- he can have a little flair! He doesn’t have to look like an accountant. On his tie, one strip is too thin, one is too fat. A really beautiful club tie has equal-sized stripes -- thick, luscious stripes. He should wear a pocket square. You’re the president, you look good, you’re the man! Screw 'em! Shepard Fairey did a painting of you because you were cool. You don’t look cool like this; you look safe.”

Takeaway: Unless you're headed to a funeral, leave the black suit in the closet. Leroy suggests adding even more color with accessories. “For me, it’s a three-way match -- the tie, the pocket square and the socks,” he says.

Father Knows Best

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Father Knows Best

Jenkins and Hunter: “Mitt Romney dresses the way we all wished our father dressed. The suits fit. The shirts fit. And while it doesn’t pertain to clothing, he knows the importance of a million-dollar-smile. One bonus point for Mitt is the neatness of his tie.”

Vidisheva: “I'm all about experimenting with fashion, but the print on Romney's tie is just awful. Are these fish?”

Leroy: “Romney, to me, is creepy. And it looks like his mom dressed him. What he needs is tinted Foster Grant glasses to add to his extra creepy appeal. What the hell are those little things on his tie? They look like little cartoon characters. You’re talking about a presidential candidate and he has a cartoon tie on? That’s fine if you’re in Hollywood and want to represent Hanna-Barbera or something.”

Takeaway: You can never go wrong with a well-tailored suit, and our fashion police recommend that all entrepreneurs make an investment in a slam-dunk piece. But one ill-advised accessory can ruin it all. “Do not wear cartoon ties,” Leroy warns. “It scares people.”

Campaign Casual

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Campaign Casual

Jenkins and Hunter: "His style, overall, is very approachable and attainable -- which is surely an effort to make him more relatable to voters. It’s appropriately casual with the light checked shirt and rolled-up sleeves, while still very crisp."

Vidisheva: “The open-button, casual print and the wedding band make Obama feel like a family man with a heart. Fit is king -- most guys’ clothing is too large.”

Leroy: “The oversized chronograph watch is a nice touch -- it’s a youthful touch. That’s really good. The checkered shirt is totally fine. He’s rolling up his sleeves. It shows off the watch. That’s the perfect example of showing a little youth. He looks more comfortable than in a suit.

Takeaway: Comfort plays a big role in personal style. “Never look like you’re trying too hard,” Jenkins and Hunter say. “Above all, be confident and comfortable.” How do you get there? “Keep it simple and fitted without being too tight,” Vidisheva advises.

Nattily Dressed

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Nattily Dressed

Jenkins and Hunter: “The casualness of the tattersall is very current. His shirts are always well-fitting with nice, clean lines.”

Vidisheva: “The shirt is age-appropriate -- a good down-to-earth look. Casual doesn't have to be boring. Have fun with patterns and prints.”

Leroy: “The checkered shirt is fine.”

Takeaway: A classic blue or white dress shirt never goes out of style, according to the Alton Lane duo, “but there's nothing wrong with some color or a bold print either, as long as it is good quality and fits appropriately,” they say.

Tee-ing Up

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Tee-ing Up

Jenkins and Hunter: “We all know one thing -- there’s only room for one trendsetter in the White House. And the president, like everyone else, knows that the First Lady fills that slot. So we forgive him for borrowing signature black-tee look from Michael Kors.”

Vidisheva: “Kudos for dressing game-time appropriate in a basic black tee.”

Leroy: "Obama works out, he’s fit -- awesome to wear a black T-shirt. It’s actually surprising to me that he’s wearing a black T-shirt. Maybe when he competes in basketball, he’s ruthless -- ‘I want to win, I’m going to command.’”

Takeaway: Jenkins and Hunter echo Vidisheva’s point: “While the days of T-shirts and blazers are behind us -- that's not up for debate -- there's nothing wrong with a solid basic tee... in the right situation,” they say.

Don't Rain on My Parade

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Don't Rain on My Parade

Jenkins and Hunter: “Mitt looks like he stepped off the cover of an LL. Bean catalog and onto the campaign trail. We can’t see much of his jacket, but he does carry red quite well, which shows he's a fan of America... and the Red Sox.

Vidisheva: "Mitt, this coat is more appropriate for middle-of-the-ocean, not a crowd- pleaser.”

Leroy: “Look at that ski jacket! He looks like he just came off the slopes. It looks like a country club parka. It’s elitist and not cool.”

Takeaway: While the panel may be split on Romney’s particular choice, Jenkins and Hunter say there’s at least one lesson here. “Stay true to yourself and always check the forecast before leaving home,” they say. “And keep your spirits up even when it's raining.”

Granddad Chic

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Granddad Chic

Jenkins and Hunter: “His charcoal suit is appropriate for someone of his age, and is always perfectly paired with a crisp shirt. The light blue tone really complements his silver hair. He’s the perfectly dressed grandfather.”

Vidisheva: “Blue on blue -- boring! At least the smile adds some flavor. It is definitely challenging for men to stand out in the crowd, but first impressions really matter, so take risks and step out of boring. This is definitely overkill for any entrepreneur. Formal business attire is a solid barrier to any customer interaction you might have.

Leroy: “The shirt looks like an English-made shirt from Savile Row or Jermyn Street in London. The tie knot …is a single knot with a nice dimple. He’s not doing that goofy thing with the Double Windsor that these politicians do. It’s very tasteful. The suit is well- cut. Perfect for a man his age. He’s impeccably groomed.”

Takeaway: While Vidisheva thinks the vice president’s look is too stuffy, the gentlemen on our panel, not surprisingly, recommend a classic style and sensibility. Or, as Leroy puts more simply, “Think Yiddish, dress British.”

Supersize Me

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Supersize Me

Jenkins and Hunter: “Ryan made a great choice of a blue tie to complement his eyes. However, he’s quite tall and narrow. Contrary to popular belief, wearing a larger size does not make you look broader -- it does the opposite. Come see us, Mr. Ryan, and we’ll get you sorted.”

Vidisheva: “The pin is a very nice touch. Ryan looks very put together. Chic and trendy.”

Leroy: “He is wearing the Double Windsor knot that just does not work. When you wear a Double Windsor knot, made famous by the Duke of Windsor, you need a spread collar. And the powder blue -- powder blue with the yellow, it’s so weak. His head is tiny and the shoulders are large. He looks completely lost in the suit. When you have a heavy widow’s peak like that, it’s not a good idea to dress like Frankenstein.”

Takeaway: While Vidisheva likes the look, the fellas say Ryan is a case study for entrepreneurs in what not to wear. “A suit needs to fit like a glove,” Leroy says. Or, as Jenkins and Hunter put it: “Never wear your dad’s suit to an investor pitch. Your appearance should not be a distraction to your message.”

Move Over, Regis

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Move Over, Regis

Jenkins and Hunter: “This monotone look is skewing a little too close to Regis Philbin territory, but we still have to give him props for the knot of his tie.”

Vidisheva: “Gingham print says this guy has heart, but the question is, does he only own blue shirts? I see men wearing the same outfit over and over again. While men never notice what women wear, guess what? Women do!”

Leroy: He’s my first choice of all the candidates in terms of his dressing. It’s perfect. There’s absolutely nothing I can critique on his way of dress. He’s top notch. The silver hair with the blue -- he’s just elegant looking.

Takeaway: “A well-tied tie can make or break your look,” Jenkins and Hunter say. “It just shouldn't be a perfect match to your shirt. The details matter.” And you need a variety of looks, according to Vidisheva. “Many entrepreneurs don't seem to realize that they should own more than one pair of slacks and a shirt,” she says. “One shirt just isn't enough.”

No Undershirts, Please

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No Undershirts, Please

Jenkins and Hunter: “It’s a very nice dress shirt, and the fit seems to be much better than we usually see from him. Although, he should ditch the undershirt -- you’re not in college anymore. And it isn’t 1994.”

Vidisheva: “It may be OK for women to show some underpinnings, but definitely not for men. Come on! The white undershirt just reads sloppy.”

Leroy: “What he’s doing here is trying to undo the hard work of Clark Gable. Clark Gable destroyed the undershirt industry in It Happened One Night, when he took off his shirt and didn’t have a T-shirt underneath. After that, no man in America wore an undershirt again.”

Takeaway: In case it wasn’t obvious: Lose the exposed undershirt!

Leather and Hound

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Leather and Hound

Jenkins and Hunter: “Clearly taking a page from Ralph Lauren’s book, his casual dress is a nice mix of rugged and refined. Although we must point out that jacket falling off his shoulders – he needs a size, or two, smaller.”

Vidisheva: “What guy doesn't look good in a leather jacket -- but the pup steals the spotlight here! I love this look. I’m glad he lost the tie."

Leroy: “Perfect. The leather is reminiscent of the World War II A-2 jackets [worn by bomber pilots]. For a man that age, it’s a really elegant way of dressing. He’s not wearing some Carhartt jacket to fit in with the construction workers. He’s just saying, ‘I’m vice president, I look elegant.’”

Takeaway: All four members of our panel are in agreement -- dress for the occasion, and when it’s time to be casual, be casual. Leroy learned that lesson years ago in Britain: “Why do you not wear black shoes on Friday, I ask? An English aristocrat would say, 'The reason you wear brown shoes is because, if you’re wearing black shoes on Friday, you’re telling the world you don’t have a country house.'”

McFitness

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McFitness

Jenkins and Hunter: “It’s great to see a political candidate dressed the way we might dress ourselves for any given sports event. Unfortunately, his jerseys and suits seem to have the same fit -- oversized.”

Vidisheva: “Grey's Anatomy has a new doctor -- move over McDreamy, your uniform is no longer in style.”

Leroy: “What is it with these T-shirts underneath? He’s wearing things too big. He has a complex where he thinks he’s small.”

Takeaway: Hey, we all make the occasional fashion faux pas. But be extra careful when you know there are cameras involved. “Don't ever take a publicity photo with a mouth guard hanging on your collar,” Jenkins and Hunter advise. “Be careful of what pictures are out there. You never know when an old picture from the frat party will come back to haunt you.”