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NEW YORK (CBS) ― When Mayor Michael Bloomberg showed up to march in a parade on Independence Day last summer, he wore a white short-sleeved shirt, a pair of bright red Bermuda shorts and a triumphant gleam in his eye.

The 64-year-old billionaire Republican, who landed on a worst-dressed list this month, was confident he could wear whatever he wanted that day, without his advisers fretting about how it looked and suggesting a change. This has not always been the case.

When Bloomberg left his financial information company to make his first run for City Hall in 2001, his stylish wardrobe of Paul Stuart suits and monogrammed shirts translated well in the public sector, and even earned him some best-dressed accolades. But his advisers often had to inform the mayor that his casual attire was all wrong.

Bloomberg was sometimes told "You look too preppy" when headed out on weekend outings in blue-collar neighborhoods. Advisers urged him to wear running shoes instead of loafers, and said the concern was, "We don't want you to look like you just stepped off the golf course or you're going on the boat later."

He had to be reminded to wear a Police Department cap at a parade or outdoorsy gear for news conferences about snow removal and Christmas tree mulching. More than once, members of the administration have handed over their Mets and Yankees caps at the last minute.

Bloomberg usually remembers those touches on his own now, but since his second term began a year ago, he has been adding what might be described as flair. In addition to the red shorts, for example, one day he showed up at a Caribbean parade in an electric pink sweater with matching socks.

And New Yorkers who don't often see Bloomberg's vacation wear got a glimpse when some news organizations captured a rare photo of him at a resort this summer. He showed up at a Sun Valley, Idaho media conference in khaki shorts, dark loafers and white socks.

GQ magazine's Style Guy, Glenn O'Brien, who votes for David Dinkins as the most stylish mayor in recent history, says Bloomberg is struggling with a problem that many men share.

"They've been well-schooled in how they're supposed to look when they go to work, but when they're left to their own devices in terms of being casual, they're just kind of lost," O'Brien said.

O'Brien notes that former Mayor Rudy Giuliani's solution was no better than Bloomberg's -- often a mishmash of sportswear and Yankees apparel.

Some observers trace the public emergence of Bloomberg's freewheeling style to a change within his administration, when Ed Skyler -- the aide that was perhaps most attentive to his attire -- was elevated a year ago from press secretary to deputy mayor.

The promotion meant Skyler no longer met Bloomberg at his townhouse in the morning or trailed him at those weekend parades, as he had for more than four years.

"There may have been more than a few times when I said, 'No, you cannot wear that,"' said Skyler, who favored Banana Republic or J. Crew business casual for weekend appearances.

Skyler ended up assuming responsibility for schooling Bloomberg on these basics, and the role simply stuck.

Early in the campaign, it became clear there was a sock situation. Bloomberg loves to match his socks to the color scheme of the day: Think pink at Caribbean festivities or green for St. Patrick's Day.

Skyler was known to mostly tolerate this quirk, but there was at least one incident where Bloomberg had to remove his socks and trade them for a more neutral pair worn by a senior adviser as the entourage rode in their SUV en route to an event.

It was 2003, during the fierce baseball playoff series between New York and Boston, which happens to be the mayor's hometown. With more than one parade appearance scheduled that day, Bloomberg dutifully wore a Yankees pullover and cap to march in a Columbus Day celebration in the Bronx.

Aides went into major damage control, however, when someone noticed red socks peeking out below the mayor's pant cuffs. Bloomberg insisted the color was to show support for Italian heritage, but to quiet the uproar, he switched to the adviser's beige pair by the time he arrived at his next event.

Skyler's successor, Stu Loeser, who occasionally had to pick out shirts for his previous boss, Sen. Charles Schumer, appears less inclined to inspect the mayor's outfits.

The general consensus in Bloomberg's circle these days is that the mayor is no longer new to the job, and doesn't need that level of unsolicited scrutiny.

But in flexing his newfound fashion freedom, Bloomberg landed on the Daily News worst-dressed list this month.

"Anybody can look good in a suit, and Michael Bloomberg generally buys only the best. But the real test is when a man varies from the formula. For Mayor Mike," the paper noted, "it did not go well."

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