Recently there’s been much ado both on and off line about Hollywood’s enfants terribles. Paris, Nicole, et al—though surely I needn’t name drop these days—have all made their debut in the courtroom this year, and their sartorial decisions have garnered almost as much speculation as their missteps.

However, if really trying to get a good read on the courtroom chic trend, one must go a bit farther back in history. Both the folks at The Fashion Bomb and She Finds cleverly pulled up snapshots of community service alum Naomi Campbell and former inmate Lil Kim en route to judicial hotspots.

Naomi Campbell

Lil Kim

Lil Kim

These femme fatales both favored tailored separates to as if to, as we all know, make us forget about their less than polished past.

Winona Ryder, as we also can recall, took the sexy-secretary route too, although hers was infused with a bit of Marc Jacobs-inspired dowdiness—a half-hearted attempt to down play the fact that her life includes a glamorous circle of friends. (Including Jacobs himself.)

Winona Ryder en route to her arraignment

Tamara Mellon—the footwear fanatic behind Jimmy Choo—didn’t bother to hide her curvaceous figure when appearing at an English court; And why not? She was en route to trounce her former husband for hiring a hacker to break into her emails! Why not flaunt what you’ve got—and earned—in any way you can?

Tamara Mellon

And Courtney Love—pre-face-lift—showed her softer, sophisticated side in a white pant-suit during her own judge QT.

Courtney Love

Alas, no courtroom chic highlight reel would be complete without recalling the fashionable figure Bianca Jagger cut at the bench when divorcing Mick Jagger was on the docket.

Bianca Jagger outside the court, 1980

Between Jagger’s charming seersucker ensemble (complete with hat!!) Winona’s demure cream suit, Love’s Victor-Victoria get-up and even Miss Mellon’s bombshell-take-no-prisoners-ensemble, all these court-ordered outfits call to mind a certain fall runway show. (I’ll give you a hint; It starts with M and ends with S. And no, it’s not Michael Kors.)

Marc Jacobs Fall 2007

After careful inspection, the savvy will see that Marc Jacobs‘ entire fall collection falls under the courtroom-appropriate category. Many a smart fashion editor dropped the term “restraint” in their review of the show, a description that provides an important key in understanding the lure of courtroom chic: Much like Jacobs’ fall collection, it’s not the simple lines, clean palette, and tailored silhouettes that intrigue fans, but the fact that these subdued designs are favored by those (Jacobs, Kim, Cambell et all) that usually opt for more pomp, circumstance, and from time to time, crazy antics. So, in sum, courtroom chic is more than just about looking pulled-together; the style’s success is all about contrast. As for the long-term success of those who wear them, the jury’s still out.

Technorati Tags: Courtroom Chic, Marc Jacobs, Naomi Campbell, Winona Ryder, Bianca Jagger, Lil Kim, Courtney Love, Celebrity Style, Free Style Tips

Photos: All Splashnews except Jagger and Jacobs which are GettyImages