The Most Iconic Celebrity Courtroom Outfits

Twitter was beside itself with joy yesterday upon seeing everyone’s favorite princess/scammer Anna Delvey take on the New York State Supreme Court in a simple, chic H&M outfit finished off with—completely out of left field—a black choker. The black choker, the accessory du jour from about 2015-2017, is a brazen courtroom choice; it doesn’t exactly express innocence but it also has a “maybe this is your daughter home from college” appeal.


Her ensemble prompted wild approval from Twitter, with writer Rachel Tashjian declaring that Delvey “looks better in court, facing grand larceny charges, than she ever did living in 11 Howard and art princess-ing!!!! GREAT WALK!” Laia Garcia labeled Delvey a “courtroom influencer”. And really, when it comes to celebrity fashion, the courtroom is the place to be an influencer. Red-carpet dresses are rarely memorable, but Lindsay Lohan’s “Fuck U” manicure at a probation hearing in 2010? Now that lasts forever.


Behold, the most iconic celebrity courtroom outfits.

The Most Iconic Celebrity Court Room Outfits 1

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Winona Ryder

2002, baby. It was a wild-west year in pop culture of Xtina’s Stripped album, The Anna Nicole Show premiering on E!, Mariah Carey’s historic MTV Cribs appearance, and Winona Ryder’s impeccably tasteful—yet mildly scandalous—courtroom outfit. Accused of shoplifting $5,560.40 from a Beverly Hills Saks Fifth Avenue, Ryder’s ensemble let us know that maybe it was worth it. From a sheer Marc Jacobs dress to a see-through sweater, they were all outfits worthy of the “FREE WINONA” shirts that ensued.

The Most Iconic Celebrity Court Room Outfits 2

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Paris Hilton

An understated black accessory such as Hilton’s headband expresses Blair Waldorf-style repentance for driving your Bentley with a suspended license. She also gets the award for most stunning celebrity mugshot for her 2007 DUI.

The Most Iconic Celebrity Court Room Outfits 4

Image via Get

Naomi Campbell

Campbell has had a unique string of court appearances, from being accused 11 times of committing violent acts against employees to testifying against former Liberian president Charles Taylor about the alleged “blood diamond” she received from him. Her outfit at the 2010 trial might win for best all-around courtroom look: a creme-colored Azzedine Alaia dress and matching sheer cardigan.

The Most Iconic Celebrity Court Room Outfits 3

Image via Gett

Lindsay Lohan

Or you can say “FUCK U” to the “I’m innocent” white button-up and demure headband and let everyone know how you really feel. During her 2010 courtroom appearance for failing to attend her court-ordered alcohol education classes, Lohan had a tie-dye manicure with one nail displaying in tiny print a message to the judge or perhaps to the whole world. Of the single “FUCK U” nail, Lohan explained on Twitter that it was a misunderstanding, saying, “… it had nothing to do w/court.. it’s an airbrush design from a stencil xx.”  

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Image via Getty

Martha Stewart

Indomitable and multi-faceted domestic mogul Martha Stewart shocked everyone when she ended up in jail for insider trading. In what was a low-key sexy suit, black heeled booties, and a Goyard bag, it was an undeniable statement piece. “If she added black opaque tights, no one would have noticed a thing. So clearly, this was an attitude choice,” author Lois Joy Johnson told the New York Daily News at the time. Martha, the baddest bitch.

The Most Iconic Celebrity Court Room Outfits

Image via Getty

Cardi B

Channeling a Russian princess meets Fran Fine, Cardi’s appearance decked out in head-to-toe fur (mink, possibly?), mirrored lime green nails, and big sunglasses is the courtroom look you could only dream of. It was also particularly well-suited for her charges of ordering someone to throw a chair during a strip club fight in Queens.

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