Playboy (PLA) is a fascinating stock. As with every trade, there are two sides to the story. One side will argue that the stock has bounced nicely off the 52-week low of $2.30, and that it has room to run as the concern continues to alter its model for making money. At some point, the bull might say, the market will become excited and buy the shares.

Interesting thesis. My argument against speculating with this idea is simple: it's Playboy. You might do well; you might not. I don't know how much plainer it can be.

Madonna is pairing up with Iconix (ICON) to launch her own fashion line, MG Icon, which will be sold exclusively at Macy's.

The line will debut at about 200 stores in time for the back to school shopping season, with Madonna providing development and promotional services. The Wall Street Journal reports (subscription required) that "the collection of apparel, footwear, handbags and jewelry is expected to retail at $12 to $40. Growth plans include fragrance as well as expansion into additional Macy's stores. Macy's will be able to launch additional brands with the joint venture."

Playboy (PLA) tends to be associated with the magazine and sex. Not the hardcore, nasty kind, of course -- Playboy has always been more than a tad distinguished, staying above board while the adult entertainment industry has chosen to compete in ways that my editor would delete if I even attempted.

With Iconix said to be interested in acquiring Playboy, it needs to think about where it can win with the ailing brand. The smart move may be to ditch the magazine and move away from sex -- it can't compete in either of these markets. Then, it needs to figure out how to make the brand relevant to everyone not in the Boomer generation ... or treat Playboy as an investment with a clock on it.

It's wabbit season!

There's only good news for Playboy (PLA) when someone expresses an interest in buying it. Shares of the ailing men's lifestyle company shot higher on Thursday when word got out that Iconix is interested in acquiring it. Iconix owns and licenses brands to manufacturers and counts Candie's and London Fog among its holdings. A deal isn't a sure thing, but Playboy now has something it hasn't in a while: hope.

Iconix has been looking to acquire more brands. And Playboy has been looking for a knight in shining armor (and with a hefty war chest in tow) since at least June, when Scott Flanders took the helm. But it looked like acquisition bait well before then, thanks to a rough financial situation.

Just two years ago, high-flying fashion designer Marc Ecko paid $752,467 for the baseball Barry Bonds used to break Hank Aaron's home run record.

Then, after conducting an online poll to determine the ball's fate, Ecko branded it with an asterisk and shipped it off to the Baseball Hall of Fame in Cooperstown, prompting Bonds himself to call Ecko "stupid" and "an idiot."

After filing for bankruptcy protection a month ago, Eddie Bauer Holdings Inc. (OTC: EBHIQ) is already seeing the suitors line up. Iconix Brand Group Inc. (NASDAQ: ICON), which owns Rocawear, is showing some interest. Hilco Consumer Capital and Gordon Brothers Group LLC are also looking to make a joint offer for the embattled clothing retailer, and Golden Gate Capital is said to be interested. Hudson Capital Partners LLC may throw its hat in the ring, as well.

Tomorrow's the bidding deadline, and there's an auction lined up for Eddie Bauer's assets on Thursday.

Already in the game, CCMP Capital Advisors ponied up $202 million in a "stalking horse bid," meaning that it will make the acquisition if nobody else beats its offer.

For now, Bauer's is living on borrowed time -- and cash. The company got court permission to take a loan for $100 million to keep the operation moving until an acquisition or auction is complete.

The private equity firms rumored to be eyeing Eddie Bauer have retail and apparel companies in their portfolios, which suggests a possibility that the company could be turned around with the right investment and management team. If not, I wonder if they'll sell the window decorations at the auction . . . always wanted my living room to look like a mall.

Nike (NYSE: NKE) has agreed to sell its Starter brand to Iconix (NASDAQ: ICON) for $60 million.

Starter is best known for its jackets bearing the logos of professional sports teams that were wildly popular during the early 1990s. As evidenced by the low price Nike is receiving for the brand, Starter has been in decline for years.

But the deal is consistent with the Iconix strategy of acquiring brands off the scrapheap and seeking to resuscitate them through licensing deals and clever marketing. Iconix does none of its own manufacturing, leaving it free to focus on maximizing brand value and selling licenses.

Iconix has been tremendously successful (take a look at the stock chart) with this approach, and owns brands including Rocawear, Danskin, London Fogg, Mudd, Joe Boxer, and Candie's.

Interestingly, Iconix founder and CEO Neil Cole is the less-known brother of Kenneth Cole, the founder and embattled CEO of Kenneth Cole (NYSE: KCP). Neil labored in anonymity for decades while his brother became a household name, but Iconix's market value has eclipsed that of Kenneth Cole. Still, numerous parties have called for a new CEO at that company.

Barron's thinks (subscription required) that it might be time to look at Kenneth Cole Productions (NYSE: KCP), which currently trades right around its four-year low. With its cash pile and strong same store sales growth, the company could be an attractive value -- a rarity in fashion stocks.

Recently, BusinessWeek looked at Iconix Brand Group (NASDAQ: ICON), the company of Kenneth Cole's younger brother Neil. Iconix has a very different business model though. The company's strategy is to acquire brands, and then license design, manufacturing, and distribution out to third parties. This leaves Iconix to focus on acquiring strong brands and developing innovative marketing campaigns. Judging from the company's robust profits and strong share price growth, it's a strategy that's working. The company currently owns brands including Candie's, Bongo, Badgley Mischka, Joe Boxer, Rampage, Mudd, London Fog, Mossimo, Ocean Pacific, and Danskin.

Interestingly, Kenneth Cole may be borrowing a bit from his brother's playbook, recently snapping up '80s icon Le Tigre for up to $25 million.

Which of these is a better buy here? The Iconix model seems to have a lot more appeal, as the company relies on license fees and is able to maintain a lean operation. The multibrand strategy also eliminates the risk of an essentially single-label fashion company.

But the contrarian in me wants to go with Kenneth Cole, the once-proud fighter whose fallen on (relatively) hard times. But given that they trade at similar valuations and Iconix has much more impressive growth, I'd probably go with the little brother.