Style & Beauty

The Best And Worst Of 2019 Courtroom Scammer Style

From Anna "Delvey" Sorokin to Elizabeth Holmes and Lori Loughlin, let's reminisce on the law's most memorable sartorial moments.

2019 was the year of the scammer: High-profile celebrity scandals satiated our collective appetite for legal drama better than “Law & Order: SVU.” And with this trend came the unexpected blessing of courtroom fashion.

Rarely does one dress to project innocence above all else, but socialite Anna “Delvey” Sorokin, actors Lori Loughlin and Felicity Huffman, and Theranos founder Elizabeth Homes gave it their best shots (unlike the male scammers this year, who were definitely guilty of fashion crimes).

Here’s who looked more celebrity than felon and who played it safe:

Anna “Delvey” Sorokin: The SoHo Grifter

Anna Sorokin arrives in New York State Supreme Court on March 27, 2019, wearing her signature choker and V-neck dress.
Anna Sorokin arrives in New York State Supreme Court on March 27, 2019, wearing her signature choker and V-neck dress.

Sorokin, who scammed under the fictional name of Anna Delvey, is perhaps the most unapologetic of 2019’s scammer squad. For those in need of a refresher, Sorokin was arrested in 2017 on six counts of grand larceny and attempted grand larceny, as well as theft of services. In layman’s terms, she posed as a German heiress, scammed her way into multiple long-term hotel stays and forged numerous checks and wire transfers. Since her arrest in October 2017, she had been held on Riker’s Island, forced to swap Balenciaga for a beige jumpsuit.

Sorokin’s court appearances began in March of this year and of course, she took her public hearings as an opportunity to let her designer-loving spirit free from its shackles. She made headlines for working with stylist Anastasia Walker for her courtroom appearances. Her looks were so memorable that an artist has even created an installation examining her courtroom fashion.

And while she isn’t known for being particularly fashion-forward, Sorokin’s commitment to character is unparalleled.

Chokers, which celebrated several recent years in the spotlight, seemingly lost their cool in 2017, the year Sorokin was arrested. But that didn’t stop her from sporting them regularly. Between her high hemlines, low necklines and thick Céline glasses, Sorokin only reinforced the persona she has painstakingly curated: the socialite who just doesn’t care.

April 22, 2019

Delvey returns from a recess during her trial at New York State Supreme Court on April 22, 2019.
Delvey returns from a recess during her trial at New York State Supreme Court on April 22, 2019.

As Delvey’s trial continued through the spring, the choker made its sixth appearance, this time accompanied by snake print and a hiked-up hemline. If forging bank documents is living on the edge, appearing at your own trial in an outfit that wouldn’t adhere to middle school dress code is living halfway down the cliff. The story — costumes and all — almost seems orchestrated for Netflix.

April 24, 2019

Anna Delvey wears a girly white dress during jury deliberations on April 24, 2019. 
Anna Delvey wears a girly white dress during jury deliberations on April 24, 2019. 

On day two of jury deliberations, Delvey appears almost as a parody of herself, in the very best way. The white dress and delicately tied bow seemingly exude innocence, though the hemline and neckline add a heaping dose of irony to communicate more of an anti-establishment message than one of submission.

Delvey was eventually sentenced to four to 12 years in prison.

Felicity Huffman And Lori Laughlin: College Admissions Scandal

Felicity Huffman, left, and Lori Loughlin, right, outside of federal court in Boston on April 3, 2019, where they faced charges in a nationwide college admissions bribery scandal.
Felicity Huffman, left, and Lori Loughlin, right, outside of federal court in Boston on April 3, 2019, where they faced charges in a nationwide college admissions bribery scandal.

In early April, spoiled by the Delvey coverage yet greedy for more, we received another tabloid treat — both Loughlin and Huffman appeared in court. Huffman played it coy, donning a simple black suit (her breakout outfit later to come), while Loughlin smiled and waved to crowds.

Initially, both women were charged with conspiracy to commit mail fraud after paying thousands to ensure their children’s admission to college. News of the scandal, dubbed Operation Varsity Blues, broke in March, exposing structural injustices within the higher education system while placing literal celebrities and their YouTube-star offspring in the hot seats. Fans shamelessly devoured the coverage.

Today, Loughlin awaits a ruling while Huffman has already completed her two-week prison sentence. Their court looks, however, will live in infamy.

April 3, 2019

Felicity Huffman, in blue shirt at center, leaves the John Joseph Moakley United States Courthouse in Boston on April 3, 2019. 
Felicity Huffman, in blue shirt at center, leaves the John Joseph Moakley United States Courthouse in Boston on April 3, 2019. 

Sept. 13, 2019

Felicity Huffman leaves federal court with her husband, William H. Macy, wearing a navy dress and jacket on Sept. 13, 2019, in Boston.
Felicity Huffman leaves federal court with her husband, William H. Macy, wearing a navy dress and jacket on Sept. 13, 2019, in Boston.

While Huffman’s most widely circulated look is her drab suit, seen in the first photo above, Huffman waltzed in and out of the courtroom like an Audrey Hepburn character in her last appearance, showing America that courtroom-appropriate and fashionable looks can exist in harmony.

No matter how many times we see her pictured in a green jumpsuit, this will be the Huffman we choose to remember.

April 3, 2019

Actress Lori Loughlin and her husband, clothing designer Mossimo Giannulli depart federal court in Boston on April 3, 2019, after facing charges in a nationwide college admissions bribery scandal.
Actress Lori Loughlin and her husband, clothing designer Mossimo Giannulli depart federal court in Boston on April 3, 2019, after facing charges in a nationwide college admissions bribery scandal.

This is Loughlin’s opening look: a camel suit, complete with wide-leg pants, a T-shirt and an out-of-place gold belt. We anticipate some bangers as she receives her due process over the coming months.

Elizabeth Holmes: Disgraced Theranos Founder

Theranos founder Elizabeth Holmes is charged with wire fraud and conspiracy to commit wire fraud and is expected to go to trial in summer 2020. She has pleaded not guilty.
Theranos founder Elizabeth Holmes is charged with wire fraud and conspiracy to commit wire fraud and is expected to go to trial in summer 2020. She has pleaded not guilty.

Late April saw Holmes, the scorned Theranos founder, attend a hearing in court in San Jose, California. It was her first public appearance since the release of the HBO documentaryThe Inventor: Out for Blood in Silicon Valley.” As the story goes, it was a noble vision — Holmes wanted to bring accessibility to labwork — but her lofty goal led her down a path of broken promises, misreported numbers and a closet full of turtlenecks.

After watching Holmes, unblinking and baritone, deliver false claims to Ted Talk attendees and old white men alike, we thought nothing could surprise us. Yet Holmes proved us wrong when she appeared in court numerous times sans her signature turtleneck, red lipstick and heavy eyeliner.

June 28, 2019

Elizabeth Holmes leaves U.S. Federal Court on June 28, 2019, in a gray suit.
Elizabeth Holmes leaves U.S. Federal Court on June 28, 2019, in a gray suit.

July 17, 2019

Elizabeth Holmes leaves a federal court after a status hearing on July 17, 2019, wearing a black dress and jacket.
Elizabeth Holmes leaves a federal court after a status hearing on July 17, 2019, wearing a black dress and jacket.

When it comes to Holmes’ courtroom style, we’ve witnessed an upward trajectory. She began her appearances in ill-fitting suits and untucked button-ups, so her graduation to a more cohesive dress and blazer combination is a breath of fresh air. The all-black reads professional, and the sheer tights add a much-needed texture change. Now we wait with bated breath for the turtleneck.

Elizabeth Holmes leaves court on July 17, 2019 without her signature heavy makeup.
Elizabeth Holmes leaves court on July 17, 2019 without her signature heavy makeup.
Celebrities In Turtlenecks