The 26-year-old star has enlisted the help of her younger sister Ali to make some quick cash after her bank accounts were recently seized by the Internal Revenue Service (IRS).
She send her 18-year-old sibling off to high end vintage clothing store Wasteland to flog some of her most valuable clothes, shoes and accessories, reported Radar online.
The 'Liz & Dick' star owed USD 233,904 in unpaid federal taxes in 2010 and despite being given USD 100,000 by her good friend Charlie Sheen, she still fell dramatically short of what she owed for 2011 and has now resorted to selling her personal effects to make up the sum.
Ali was seen arriving at the Los Angeles shop with several bags bursting with designer wares, but was shocked when the manager offered her a great deal less than she was expecting.
"Thirty dollars for these? They cost USD 700! This is ridiculous," a source said.
The aspiring model then tried another tactic to increase the value of the items, which included a pair of Chanel pumps and a Balenciaga handbag, by listing all the occasions her famous sister had been pictured wearing them.
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However, the manager stood firm and Ali left disappointed.
Money is not Lindsay's only worry; the starlet was charged with misdemeanour assault after an altercation at a New York nightclub in November, and could have her probation revoked due to lying to police about being behind the wheel of a car accident in June.