Dressing down for celebs in court

Winona Ryder, 2002
The girlish side-parting, the twee, childlike dress, eyes nigh on brimming with innocence:

here is the court look that proposed, and duly confirmed, the idea that one could, just as Roxette promised us all, dress for success. Now, back in 2002, Winona Ryder was not exactly surfing the A list.
Well, a decade of starring in such self-indulgent toss as Girl, Interrupted and Autumn in New York does nothing for a girl’s cred. Oh, and then there were those pesky theft, burglary and vandalism charges.
But, happily, she was able to give her old mucker Marc Jacobs a call, and he duly kitted her out in dresses with pussy bows and blouses with Peter Pan collars and ballet pumps. Sadly, this wasn’t quite enough and she had to put in some community service or whatever but, hey, who cares? At least she looked good, right? And that’s the lesson a lot of her followers seemed to learn.

Paris Hilton, 2007
The mental processes are as sharply visible as the multiple collars overlapping one another like a triple cheese-burger.
Here she is, the little cherub, doing her darndest to dress like a – whaddyacallem? – civilian. You know what she means – like, those boring people who get up and go to work and go to the supermarket totally think that “trust” means “belief” as opposed to, you know, “fund”.
But the way she’s wearing a button-down shirt and a waistcoat and a jacket ... well, really, its like seeing a baby foal attempt to take it’s first steps, isn’t it? Aiming for normality, but falling on its ass, frankly.
Note, too, how she made sure that her jacket sleeves went only halfway down her arm so that she got proper credit for wearing full-length shirt sleeves as opposed to her usual top de choix, a ripped vest top.
Oh, Paris! Je l’adore!

Naomi Campbell, 2007
“What do they expect me to do – walk in looking all drib and drab (sic)? I’ve never looked drib and drab in my life.”
Thus speaketh Naomi Campbell in the diary she nobly kept during her recent community service and, really, it’s a piece of literature that surely merits the description “this generation’s Anne Frank” across the top (best line: “I never had problems with men, because if they bothered me, I’d tell them to xxxx off”).
OK, so it’s not exactly a photo from court, but surely this image of our Naomi leaving the New York sanitation department at the end of her community stint shows how justice and fashion and, well, just love in general can come together in one big, happy ending. And there’s something about the juxtaposition between a Dolce & Gabbana dress and the word “sanitation” on the truck behind her that just gets me ... right there.