Holly Madison

Hugh Hefner’s #1 girlfriend, Holly Madison, was out dropping some serious cash on Robertson Boulevard. What do you think of the Girls Next Door star’s style? Holly was wearing a black off-the-shoulder shirt, denim skirt, knee-high tubesocks and a pair of Converse All-Stars. Oh, and don’t forget the Louis Vuitton handbag.

Her outfit is fun, I guess. I think she’s beautiful, but I’m not sure that I think this is her best look.

Oh well, she’s got all the time in the world, and Hef’s money, to try out crazy styles.

So what is going on with Hef’s two other girlfriends?

There was the recent announcement that Kendra Wilkinson will be moving out of the Playboy Mansion next season to do her own spinoff show, there are rumors flying around the gossip mill that Holly and Hef may be getting more serious. Wedding bells? I don’t know how that will work. Hef is supposedly still legally married to his second wife, Kimberley Conrad. Conrad and Hef’s two sons Marston, 18 (Hef’s middle name) and Cooper, 17 live next to the Playboy mansion in a $7 million home purchased by the Playboy mogul to keep them close. Kimberley and the boys visit the mansion regularly. In fact, Tuesday night is “family night” and there are no girlfriends around. Hefner and Conrad split in 1998, but the two are still technically married. Hef would have to officially divorce Conrad in order to marry Holly.

In addition, Hefner’s other girlfriend Bridget Marquardt was overheard talking about a huge wedding coming up, and that she would be moving out as well. “She said they (Bridget and Kendra) will be moving on since Holly is Hef’s main girlfriend.”

What do you think?  Should Hef finally get a divorce and marry Holly?  Sorting out the finances of that divorce would probably take years.  Conrad has been Hef’s wife legally for almost two decades.  Or should Hef just leave Holly a nice chunk of change in his will so that she is taken care of after his death?  I watch the Girls Next Door and Holly has hinted on more than one occassion that she wants the Playboy mansion.  I think it should go to his children.