NEW YORK – Friday was the most expensive day of Britney Spears’ life. In the work of an evening, the young woman who was once the world’s biggest pop star may have sabotaged her image, her income and her personal life in a breakdown that could cost her a fortune.

“Without question, parents are going to have a hard time allowing their kids to buy anything associated with Britney,” says Doug Akin, a partner with Mr. Youth, a marketing agency that works with lifestyle brands trying to capture the teen market.

“I think the concern here is the excessiveness and I think it is certainly dicey for a major corporation to associate with someone when they are at a stage like this,” Akin said.

This weekend’s shearing also tips the scales in favor of ex-husband Kevin Federline. The pair’s messy separation continues – this month, Federline reportedly turned down a divorce settlement offer of $25 million to relinquish rights to spousal support and custody of their two baby boys.

“What this means to Kevin is a bunch more zeroes -and in the right place,” said prominent divorce attorney Sue Moss. “She is going to have to buy her way out of this one, and it’s going to cost a lot more than a tattoo.”

Over the course of her career, Spears has endorsed products from Pepsi to face cream.

In 2001, Pepsi paid Spears their largest ever endorsement fees – tens of millions of dollars – to be the face of their brand. Her own perfumes have been top sellers since 2004.

That’s helped her amass a net worth Forbes estimates to be at $100 million.

But getting another high-profile endorsement now seems unlikely. “I would expect her to take a hit short-term, because you’re going to get a lot of knee-jerk reactions out there,” says branding expert Rob Frankel. “I would not be surprised to see corporate sponsorships drop away.”

Still, some argue that today, there is very little a celebrity can do to permanently damage their brand.

In the wake of Anna Nicole Smith’s tragic story of excess, the American public may be unfazed.

“People are putting the pieces together and saying it’s not “brand Britney, the mess,’ but “the person’s a mess,”‘ says branding expert Jonah Disend. “Hopefully, she’ll get help.”

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(New York Daily News correspondent Mark Ellwood contributed to this report.)

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AP-NY-02-19-07 1725EST