The Fashion Whip: Does Mitt Romney Dress Too 'Rich'?

Fashion Whip is a political style column by HuffPost DC reporter Christina Wilkie and personal stylist Lauren Rothman, inspired by Lauren's experience at Styleauteur , the firm she founded. Follow us on Twitter at @FashionWhip .

WASHINGTON -- I recently met with a wealthy government contractor in Washington who owns a half-dozen designer watches. "What's the deal with watches?" he asked. "I still wear my Timex every day to meet with government types, but I've got a box full of Breitlings and Piagets at home. Is there anything I can wear them for?"

As we discussed his options, an elected official walked into the room and joined our conversation. "Is it the same for cuff links?" he asked. "I've worn military uniforms for most of my career, and I still feel like my good cuff links are only for 'date nights' with my wife. Would I look overdressed if I wore them to work?"

"The answer comes down to two things," I said, "your authenticity and your audience."

One might think owning a nice watch is reason enough to wear it, but in Washington, that's not always the case. Here, professionals walk the line between the private and public sectors, and plenty of them believe a "working man's look" with shirt sleeves rolled up and a tie pulled loose will win them points.

Both of these men had to ask for money a lot at work -- the politician for campaign donations, the contractor for government loans. After our conversation, they decided to leave the cuff links and big watches at home, where they could never undermine these requests.

But the "audience" tactic can backfire if it's not authentic. Just ask Mitt Romney, who has struggled to appear relaxed in casual clothes for years, and whose jeans and unbuttoned collars often come across as awkward to voters.

As recently as this month, Romney's jeans were the subject of ridicule from MSNBC 's Chris Matthews, who called Romney "the guy with his -- whadaya call 'em? -- 'mom jeans' or whatever he wears. What is that costume that he wears? What is that costume? Nobody wears clothes like that."

And herein lies the key: wearing something really special is great, but wearing a costume for political reasons always looks phony. Romney is clearly more comfortable in the beautifully tailored Italian suits and perfectly creased blue ties he likes to wear on TV.

And it's little wonder, after twenty years at the helm of Bain Capital, that Romney is accustomed to the suit-and-tie look. It's authentically who he is, and that's why it works.

Even without flashy jewelry (leave that to Texas Gov. Rick Perry ), Romney's wealth oozes from his gray flannel, and his look plays right into a narrative the Obama campaign hopes to drive home if he's the nominee this fall -- that he's a rich "vulture capitalist," disconnected from everyday Americans.

But for now, the sharp tailoring sets Romney apart the good way in a crowded primary field. So much so that another GOP hopeful, Rick Santorum, out-and-out copied Romney's debate look in South Carolina last week, trading in his signature blue shirt, navy suit and prep-school tie for a white shirt, pale blue tie, and gray suit. In a business driven by perception, clearly Santorum wanted to be perceived as a front-runner.

Meanwhile, the contractor I mentioned earlier decided to save his good watches for parties at his house. And the member of Congress? He said he plans to wear his cuff links to his daughter's wedding later this year.