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Sorry, Gwyneth!
Courtroom fashion has a fascinating place in pop culture history. In 2019, the media storm around Anna Sorokin’s trial provided enough Fake German Heiress fashion fodder to inspire choker-heavy Halloween costumes to this day. Gwyneth Paltrow’s 2023 Deer Valley skiing accident court appearances cemented her status as a stealth wealth icon after wearing head-to-toe The Row and spurring thousands of fast fashion knockoffs with a single belted sweater. And Cardi B showed up outside a Queens courthouse in glamorously monochrome winter white just a few weeks beforehand.
Throwback court fashion is even better, though. It will never not thrill me that Winona Ryder wore a dress by Marc Jacobs… to a court hearing about shoplifting at Marc Jacobs. And I’m still looking for Lindsay Lohan’s 2011 probation hearing dress on The Real Real. And who could forget the iconic Bling Ring trial voicemail monologue? Nancy Jo, this is Alexis Neiers calling…
The mid-aughts were truly the golden era of courtroom fashion. Before Gwyneth put Deer Valley on the map and Cardi took her Louboutins to trial, there was Martha Stewart—the original trendsetter of serving while being served.
In case you didn’t catch Martha, the new Netflix documentary on the entertaining icon that debuted earlier this week, here’s a little refresher: In 2003, Martha Stewart faced accusations of insider trading. A heavily broadcasted weeks-long court case ensued in January 2004. (Stewart would eventually be sentenced to five months in prison after being convicted—notably, not for insider trading.) It was a publicity circus. The queen of etiquette and entertaining on trial? The irony did not go unnoticed by the media, but Stewart approached the intense public scrutiny with grace and lots and lots of style.
In fact, nobody does restrained color theory and quiet luxury quite like Martha. (Sorry, Gwyneth!) Martha acts as a reminder of just how modern and chic her mid-2000s court style looks remain. So, let’s all take a lesson from Martha Stewart—not on when to create your cranberry Thanksgiving centerpiece or why to brine your chicken—but on how to dress for success when the world is watching.
Always Bring Your Birikin
It's a flex, to be sure. But toting around a $10,000 Hermès handbag to a meeting with your lawyer is just the sort of insouciant opulence that captures the public imagination. Tongues will wag.
Is it in poor taste? Perhaps. But like Diana Vreeland said, "A little bad taste is like a nice splash of paprika." It's not a memorable look without it. And when you're already on trial, what's a little fashion controversy?
Outerwear Is Everything
There are two important moments to consider in courtroom fashion. Your outfit during the trial (the one the judge will notice), and your exit look for outside the courthouse (where all the paparazzi camp out).
The latter is where Stewart shines. There was never a coat wardrobe quite like hers in the winter of 2004. Feast your eyes on Stewart's collarless coat in an ultra-chic (and very 2024, might I add!) shade of chocolate brown. Her slouchy, greige jacket would look right at home in a Toteme or Loro Piana spring/summer '25 collection.
And I think we can all agree that a floor-length ladylike overcoat is a forever closet staple. (I'm certainly adding one to my wishlist.)
Accessorize Like You Might Be Going Away
Cashmere scarves and cultured pearls aren't exactly in the Orange Is the New Black playbook, so naturally, Martha got some good use out of her go-to accessories during her court case appearances.
Let's start with her jewelry collection. The media scion and Snoop Dogg bestie is a big fan of pearls. She has a champagne-colored choker-length necklace for more formal occasions, a trio of long strings for more playful pearl styling, and a pair of gold door knocker earrings for everyday wear—and she wore them all during her 2024 trial.
She also put on an excellent outdoor accessory display; the court case was during a bitter East Coast winter, after all. She convinced me that buttery leather gloves and a brown tippet are the ultimate Rich Mom investment piece (it's the little things). Plus, her cashmere scarf collection appears boundless—it seems she never leaves the house without one.
Finally, these stellar black heels deserve an honorable mention. The whole look is very Bella Hadid-coded in a slinky, office-siren way.
Layer, Layer, Layer, and Then Layer Some More
Martha Stewart just gets it. If your outfit lacks color and volume, you need to get creative with texture for visual interest. And if your look lacks texture, pile on the layers.
As the queen of prissy, understated neutrals, Stewart nailed the quiet luxury thing way back in the mid-aughts when The Row was nothing more than a twinkle in Mary-Kate and Ashley Olsen's eye. And it's her expert layering that deserves much of the credit. Adding a flash of red via an oversized popped collar is nothing short of inspired. And this meditation on baby blue is even chicer than I remember.
Keep 'Em Guessing
A mini skirt? To court??? Stewart truly refuses to let the haters get her down. Almost 10 years after her 2004 insider trading case, Stewart returned to the New York City legal system when she was called to the stand in 2013 to testify about her company's agreement with JC Penney.
Undeterred by her past, she pulled out all the stops for the occasion, wearing a fun matching set and straight-from-the-salon highlights. The brown vest is classic Martha—as is the visible collar—but the unexpected length and architectural details make it a look for the ages. And with a digital camera in hand, she really ate with this one.