Like mother, like son. Sean Preston Spears, the 11-month-old son of pop star Britney Spears and hubby Kevin Federline, has already begun to follow in Mom’s illustrious footsteps. Star Magazine reports that Baby Spears has been named one of “The Worse Dressed Men in the World,” in the September issue of Esquire Magazine. Quirky editors told Sean, “As soon as you gain the dexterity, straighten out your hat.” Spears joins the ranks of “Worst Dressed” with other fashion-not-so-greats such as Axl Rose and Marc Anthony. Tough break, Sean. Next time you’ll learn not to use Mom’s stylist.

Being the trophy girlfriend of Playboy founder Hugh Hefner pays. Really. Star Magazine reports that the 80-year-old’s will provides a substantial chunk of his $80-million estate to live-in girlfriends Holly Madison, Kendra Wilkinson and Bridget Marquardt (featured on the show “The Girls Next Door”). “Holly gets $3 million and Kendra and Bridget each get $500,000, provided that they are still living with him at the mansion when he dies,” a source said. Further stipulations of Hefner’s will: Estate trustees will decide who gets Hef’s frozen sperm, his older children Christie and David will receive a third of his estate and the Playboy Mansion must never be sold. Hey Hef, looking for a brunette college-educated woman with writing skills? Contact The Northerner at 572-5859.

Actor Tom Cruise is back at his old tricks. No, he is not planning to romp on Oprah’s infamous couch again. Cruise is, however, planning on making daughter Suri’s first splash on the paparazzi scene as sensational as possible, U.S. Weekly reports. The offspring of TomKat has yet to be seen by anyone but close friends and family, but that may soon change. Cruise, 44, set up a photo shoot of the then 3-month-old and her mom, Katie Holmes, 27, July 31 with celebrity photographer Annie Leibovitz. The photos are supposedly set to debut in Vanity Fair this fall, but Cruise’s reps refused to comment. “Tom did this to build attention,” a Cruise insider said. “And to make it a bigger deal than the Shiloh pics.” Way to go Tom. You’re going to one-up a 6-month-old.

In other Cruise news, Cruise/Wagner productions, Tom Cruise’s production company, parted ways last week with former backers Paramount Pictures. Previously, Paramount had first rights to finance and distribute Cruise/Wagner films, and in exchange, Paramount paid the producers a salary of $10 million per year for salaries and expenses, msn.com reports. The partnership ended when Paramount offered a paltry $2-million to renew the deal. Apparently, Paramount’s change of heart (and cash) was a reaction to the actor himself. Sumner Redstone, chairman of Paramount parent Viacom Inc., told the Wall Street Journal that the actor’s public behavior, including his heated defense of Scientology, alienated moviegoers and cost Paramount money at the box office, between $100 million and $150 million in ticket sales for Cruise’s latest film, “Mission: Impossible III.” That couch-romp cost Cruise more than just his dignity.