Not a solution for the particular clothes you are having problems with, but perhaps a help for the money situation.
You can use this hang-on-the-wall hacked dresser to shop for outfits for free:
http://www.modthesims2.com/showthread.php?t=225251Or you can use the family funds cheat to add back in specific money amounts which have seemingly gone off into neverland:
familyFunds
familyname amountFor example:
familyFunds Smith +94
will add 94 simoleans to the Smith family's total.
The familyFunds cheat, IIRC, requires you have Nightlife installed.