It's hard to tell who's giving worse advice these days: the financial advisor to the Kardashians, or the marketing department at Sears Holdings (Nasdaq: SHLD). But it's apparent both have taken leave of their senses, now that the sisters will be marketing a line of clothes at the once-venerable retailer.

A dash of salt in the wound
After the public-relations disaster that followed their endorsement of a fee-laden prepaid debit card, the Kardashians' advisors seem to believe that teaming up with a company whose Kmart unit had Martha Stewart hawking her wares there would take away the sting of being sued for breach of contract.

Revenue Resource Group, which issued the Kardashians' branded MasterCard debit card, is taking the trio (and their mother) to court for $75 million for backing out of their deal. It seems that all the negative publicity over just how awful the card was for consumers made the Kardashians think they better take a raincheck.

Enter Sears, which will launch a line of ready-to-wear clothes, handbags, lingerie, jewelry, and shoes "that embrace a woman's natural curves through bold and beautiful fashion statements for all occasions."

However, the Kardashians run their own chain of stores called DASH in tony neighborhoods like Calabasas, Calif., Miami Beach, and the Soho area of New York. Their high-profile, conspicuous-consumption lifestyle hardly comports with your typical Sears and Kmart shopper.

High fashion, low prices
It's not unheard of for the fashion designers to dress down their clothes, selling more moderately priced lines at discount venues. Martha Stewart's run with Kmart was one example, but high-end designer Vera Wang also teamed up with Kohl's (NYSE: KSS) for a line that eventually spun off into mattress accessories and other household gear. Target (NYSE: TGT) and Mossimo have been an item, and Issac Mizrahi had a stint there until the two broke up in 2008. Nicole Miller sells duds at J.C. Penney (NYSE: JCP) while Cynthia Rowley is making designer diapers for Procter & Gamble (NYSE: PG).

These partnerships often raise designers' profile and help support their high-end lines. They're reaching far more consumers than they otherwise would by maintaining their usual exclusionary markets. The mass markets benefit from exposure to high quality, top-notch design. But, um, is anyone arguing that the Kardashians are underexposed?

Wait! I've got an idea...
I find it even more improbable that someone at Sears actually agreed this was a good idea. These women are famous simply for being famous -- and for one sister's decision to film her more intimate moments with a boyfriend. They attempted to cash in on their fame by offering a debit card that would have soaked its users with high fees and even higher interest rates. And these are the people with whom Sears wants to align its image?

Dash for the exits
Rather than look to the successes that other department stores have had with high fashion, Sears would be wise to heed the mistake that was Wal-Mart's (NYSE: WMT) foray into the fashion scene. People simply didn't go to the deep discounter for high-end clothes; they wanted good value on everyday items. Trying to hawk trendy duds was a debacle for the Bentonville Behemoth from the beginning.

Sears is circling the abyss, latching onto anything to seem relevant. There was the Christmas in July program and layaway promotions. It wanted to be the neighborhood pawnbroker by offering cash-for-gold services. It sold underpowered $150 tablet computers and stayed open for the first time ever on Thanksgiving Day. None of these stunts has successfully lured shoppers into its stores en masse.

Sears is out of its mind if it thinks this deal with Kim, Khloe, and Kourtney will help it turn the business around. Investors are crazy if they think Sears is a good investment anymore. Its slow, steady erosion of value is almost complete.

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Fool contributor Rich Duprey does not have a financial position in any of the stocks mentioned in this article. You can see his holdings here. The Motley Fool has a disclosure policy.