Hugh Hefner, reportedly unhappy with LiLo’s first Playboy shoot, had the professional ex-convict come back to the manse for a second photoshoot with a second photographer. But fear not pervs, the Lohan Playboy issue is still scheduled to hit newsstands for January. However, don’t expect her to go all spread eagle because this is a classy affair. We’re talking tits out but panties on. Because she’s a frikkin’ lady and don’t you frikkin’  forget it! [E!]

*Sidebar: Can we talk about how the Lohan has spent more time behind bars than most rappers, which I think is a sad commentary on the state of hip-hop today. When a white girl from Long Island who was a Disney star before puberty has more street cred than you, it’s time to hang up the mic and call it a day.

What: Boardwalk Empire, Season 2

When: September 25th, 9 p.m.

Where: HBO

Trends to look for: Fur, beaded flapper dresses, red lips, Marcel waves, three-piece suits, cigarette holders, long pearls, cloche hats, fascinators and watch fobs

Let’s start with the best of the Derby, the Southern Belles who embodied the spirit of the event in a tasteful and classic manner.

Johnny Weir is the winner of best dressed! He looks amazing in his dandy ensemble and gorgeous oversize hat.

Ashley Simpson looks absolutely adorable (something I don’t get to say very often) in her cloche hat, pearls and polka dots. It’s 1922 at the Derby and she is in high style. But I wish she would have put her hair up.

I love this bright periwinkle dress Jaime Pressly chose to pair with her dark hat and shoes. But I can’t tell if the dress is wrinkled or not, which is a little irritating to the eye.

Doesn’t LeAnn Rimes embody the spirit of the Derby perfectly? I really adore the floral mini dress and how the ribbon on her elegant straw hat matches it to a T. I would have done a different shoe, but that’s me.

Joey Fatone is certainly N*SYNC with the festivities (forgive me, it’s Friday and I’ve already started with the juleps). Give me red roses and feathers any day of the week.

This is a very special photo that will take us from the best dressed at the Derby to the worst dressed. Kim Kardashian looks absolutely gorgeous. Her look is sexy and sophisticated, and I especially love the hat and wrist gloves. Brava, Kim.

Kris Kardashian on this other hand looks a mess. This dress is not flattering on her and the patent leather stripper shoes were a poor choice for the event. AND I could make a leather tote bag out of her sun damaged skin. Bad, bad, bad.

God in heaven, save us from the evil that is Brooke Shields‘ hat. It seriously looks like her whiny kids made it for her in school – a failed attempt on Brooke’s choice to wear it and the children for being poor crafters. And I think I had this same dress when I was five, so maybe she borrowed it from her daughters too?

I was a little torn here, because all of these hats are fabulous. Kenda look bangin’, she is actually one of the best dressed in my opinion. HOWEVER, where in Satan’s hell did Bridget and Holly get those dresses? Macy’s junior department prom section is about on par with these disasters, couldn’t they get anything better? Wait, probably not. Hef also looks pretty fly for a 200-year-old man.

An all black outfit to the Derby? Are you f*cking kidding me Gabrielle Union? In the words of Carrie Bradshaw‘s unfortunate party girl friend Lexi Featherston, “I’m so bored, I could die.”

And here it is, the absolute worst outfit of the 2010 Kentucky Derby. Bethenny Frankel opted for a light pink seersucker jumpsuit with matching ruffle, side tail and hat. But I think the lollipop is what pisses me off the most. It kind of looks like she wrapped herself in a baby blanket, no?

I hope you enjoyed this very special Kentucky Derby edition of Red Carpet Report Card. Stay tuned for the best and worst dressed at this year’s event next week.

- American Apparel sleaze, Dov Charney, wants to live the Hugh Hefner lifestyle: hopped up on so many ‘ludes and Viagra he won’t know when he’s coming or on who. [Styleite]

- The world’s most expensive shoe costs nearly $230,000 and is made of solid gold and over 2200 diamonds. That’s nothing, I’ve got the world’s most expensive Crocs:  $250, made of solid plastic and Cubic zirconia. It goes really well with my world’s most expensive velour tracksuit. [Telegraph]

- Noted Jew, Donna Karan, thinks John Galliano‘s anti-Semitic remarks were “”blown up out of proportion.”  Karan goes on to say that Galliano is “a wonderful designer, a brilliant designer, and he probably needs help and support right now.” Well, I already know of someone who’s on the help and support bandwagon. [The Cut]

- Remember when Matthew Williamson said that Kate Middleton “isn’t a fashion bunny” and “I don’t know why everyone in fashion is waiting to see what she wears. I’m, like, thinking: get over it.” Well, turns out he was just “misquoted”: “I was referring to the fact that I’d been asked about her three times previously in the same night so it was more that I was over the fact that I’d been asked repeatedly about her. I’m setting the record straight: I’m a big fan and I’m sure she’ll make an amazing choice [for her wedding dress].” Yeah, that record is about as straight as Elton John‘s Oscar party. [Fashionista]

Holly will be rated on the below categories, five being the highest and 1 being the lowest.

Fit: 5

Appropriateness: 4

Trendiness: 4

Styling: 5

Shoes: 4

Hair: 5

Makeup: 5

Pose: 5

Confidence: 4

Holly was always my least favorite Girl Next Door, but she’s definitely the classiest, even though she usually acted like a bitch on the show. She looks great in this dress, the hair and makeup isn’t too much and she’s working it for real.

In her memoir, Bunny Tales, Izabella St. James paints a portrait of carpets soiled by dog poop, Quaalude- and Viagra-induced sex with Hef and A-list celebrities and birthday cosmetic surgeries footed by the old man himself.

In describing sex with the quintessential playboy, St. James said “he just lay there like a dead fish.” That’s a bit insensitive. He’s not dead yet, after all. St. James goes on to explain:

“We often wondered why he did it at all. He must know deep down that it is just a show. But he is trying to live out this fantasy he has been selling to people since 1954. He wants to live up to the Playboy image he created and the expectations people have of him.”

Even more disturbing, if that’s at all possible, Jill Ann Spaulding reveals that Hef didn’t use condoms.

“There was no protection and no testing for sexually transmitted ­diseases.”

Gross.

After refusing to have sex with Hefner, Spaulding was “quickly dismissed” from the mansion. Put out or get out, lady.

I’m always wary over tell-all memoirs, because people are trying to sell books after all. It’s not surprising that the Playboy mansion would be totally skeevy. Charlie Sheen frequents it for a reason.

However, I’m taking this information with a grain of salt. And a vial of Valtrex.

LINK LOVE: Daily Mail

Hef, naturally, took his Twitter to announce the news, which is surprising because usually people his age have no idea what the Twitter is. Or the internets. Or, for that matter, a computer.

Hef’s two previous marriages — to Mildred Williams in 1959 and to Playmate Kimberly Conrad in 1989 — each lasted about ten years, so that bodes well for Crystal. Hef, on the other hand…well, he’ll hang in as long as he can.

Despite their 60 year age difference, Crystal maintains that her love is true and she  has no ulterior motive:

“I would say that I’m not after Hef for his money. I have my own career going.”

Well, it’s nice that she “would say” that. I would say that Hugh Hefner is the biggest pimp that ever walked this planet and that he’s too smart to not have her sign a pre-nup.

Congrats to the happy couple!

LINK LOVE: MTV News

Is this Lauren Conrad or Carmen Electra? Guess we’ll never know, due to the high amounts of photoshop.

Oh a side note, I want that playboy bunny garment (if you can call it that). I think it would go nicely with my Hugh Heffer blow up doll.

Thanks Scandalist for the pic

Well maybe the kid wasn’t taken away, he probably just ran away after his mother threatened to wear these pants again. There are plenty of times when leopard print is acceptable in moderation, but there is not a single positive word I can say about this picture. I’m surprised PETA isn’t on her ass for skinning a cheetah to make those ugly things, and then defacing the whole race of animal by wearing them in public. Besides having vomit pants, she’s wearing the slipper Hugh Hefner died in (he’s still alive? really?), Jessica Simpson’s tard smile, and a hairdo that is fitting of one of those embarrassing celebrity mug shots. Do us all a favor and disappear for a couple years Sharon, that should give you plenty of time to realize what you’ve done, and what happened to all the money you made for doing the movie Antz? Oh right collagen, I hear it’s expensive.

Thanks to Pacific Coast News for the picture.

At last week’s Dolce and Gabbana show the theme was ‘glamorous shut-in’. The Italian designing duo paraded model after model wearing updated old school, gentleman’s PJ’s. I couldn’t help but wonder if the collection wasn’t inspired by Playboy founder Hugh Hefner? Hear me out, nobody has done more to popularize the satin pajama as a normal evening attire than Mr. Hefner.