The Best Celebrity Courtroom Bags

Gwyneth Paltrow is seated in a spare room: she’s wearing a simple pale blue office shirt, her hair is casual, and her makeup is minimal. 

She says, “Yes, Astronomer is the best place to run Apache Airflow, unifying the experience of running data, M.L. and A.I. pipelines at scale. We’ve been thrilled so many people have a newfound interest in data workflow automation.” She says it with utmost sincerity and a slight smirk on her face. We understand absolutely nothing about her statement. 

Needless to say, the video goes viral. 

“Celebrities,” says PR strategist Evan Nierman, “have a unique ability to recover from embarrassing gaffes or situations that would ruin the careers and potentially the lives of normal day-to-day people.”

And for a corporation like Astronomer the backlash of the Coldplay debacle at the time, Paltrow proved to be the ideal spokesperson, not just for the earnestness with which she peddles her raw goat milk cleanses (with questionable health benefits that continue to frustrate medical experts and, of course, continue to sell out), but also because she’d just ridden the high that was her Utah ski trial, arguably the exact moment in human history when the entire stealth wealth trend was conceived in the first place!

You see, celebrity courtroom appearances have become their own unique campy tradition: stars keep getting themselves embroiled in scandals (sometimes involuntarily), which occasionally lead to legal proceedings, and with that, outfits that match the occasion and the bags to boot.

Of course, we’re hooked; who wouldn’t be?

Understated All the Way

Now, Paltrow’s ski trial wardrobe wasn’t just good, it was disarming. 

The kind of dressing that looks effortless until you remember that nothing about Gwyneth Paltrow has ever been accidental. Cream knits that would put any other beige-fluencer these days to shame, crisp button-downs, impeccably tailored blazers that sit just so, a practical rotation of Prada and Celine boots that say I walk places, even if those places are mostly Aspen-adjacent, and of course, the exact antithesis of Bridget’s Burberry bag from Succession, all rendered in a palette of cream, camel, navy, and gray.

And speaking of accessories, there was that sly wink – Paltrow’s choice of enormous eyewear when she herself was being sued by a former optometrist!

The entire wardrobe – or rather, court-robe, in pop-culture speak – reeked of stealth wealth, unfolding in real time alongside Succession’s season 4, spawning hundreds of shopping articles in its wake (not to mention, serving as a walking, talking Goop advertisement.) But it’s also stealth persuasion. She dressed like someone who didn’t need to convince you of anything.

Which, frankly, is very convincing.

This form of visual storytelling was what Winona Ryder tapped into back in 2002, when she appeared in court decked out in Marc Jacobs for shoplifting… Marc Jacobs merchandise, a Fendi Mama Baguette in tow. Rihanna, in support of A$AP Rocky, showed up in Saint Laurent tailoring with a Bottega bag. Even Paris Hilton, the patron saint of excess, traded in her rhinestones for restraint, with a demure Chanel flap tucked underneath her shoulder.

The underlying implication here is that here’s someone who’s not just innocent, but also in control. Calm. Unbothered. A woman who would absolutely remember to bring her reusable bag.

Minimalism Who? Enter, Maximalists

Then, of course, there are those who refuse to play that game.

Kim Kardashian, for one, has never once pretended she wants to fade into the background. When she arrived at a Paris courthouse ahead of bestie Lauren Sánchez’s wedding to Jeff Bezos, dripping in diamonds and vintage Galliano, flanked by Mama Kris and her Mini Kelly, subtlety was clearly not the brief.

And why should it be, after all? The jewels weren’t decorative – they were declarative. You can take things from me, they said, but you can’t take this.

Cardi B operates on a similar frequency. Her self-described “court flow” era gave us fur coats, sculpted power suits, towering heels, and an almost comical number of Hermès Birkins. It was fashion as much as it was bravado, wealth worn loudly as both armor and distraction. While the allegations against her left something to be desired, her commitment to the bit certainly didn’t.

And of course, if it is the Birkin that we speak of, we must mention the OG, Martha Stewart. Rolling up to court for insider trading charges with a purse that costs as much as a down payment on a car remains one of the most outré flexes of wealth a celebrity has displayed within the confines of the courtroom. The message was clear: come what may, but Martha Stewart will still be Martha Stewart.

In the list of unapologetic courtroom-dressers we must further mention Anna Delvey, whose rotation of Saint Laurent, Victoria Beckham and Michael Kors and signature Celine frames merited its own Instagram account, @annadelveycourtlooks and the hit Netflix show Inventing Anna, Naomi Campbell, who famously rolled upto community service in a sequined floor-length Dolce & Gabbana gown, and Lil’ Kim, in a tan suit, French tips and a monogrammed Louis Vuitton purse.

It was as if to say – no, scream – they’re innocent, even if proven guilty.

The Psychology and Psyche of the Court-robe

All this to say, at a setting as emotionally charged as the courtroom, fashion lives at the intersection of psychology, performance, and power. And for celebrities, the outfit becomes one of the few remaining tools for reclaiming agency in a situation designed chiefly to strip it away.

I.e., when lawyers do the talking, outfits fill in the gaps.

But done right, the court-robe is more than a sartorial mirage. In Winona Ryder’s case, the Marc Jacobs on Marc Jacobs sentimentality led Jacobs to deem her the “ultimate muse” and cast her in campaigns for years after.

But handbags – as Wednesday Martin writes in The Primates of Park Avenue, “With a gorgeous bag, I thought, I would not just have a sword and a shield. I would have something that they did not have, or something they wanted, or something they did have and didn’t want anyone else to have,” – carries a strange emotional weight. They’re practical, personal objects, but also deeply symbolic. And the bag that is carried into the courtroom? The ultimate armor.

At the end of the day, there’s something inherently camp about dressing glam for punishment. It’s defiant. It’s theatrical. It’s a refusal to disappear quietly. Susan Sontag would absolutely get it. At its best, it’s ingenious. At its worst, it’s grotesque. Often, it’s both at once. Maybe the celebs are in on the joke. Maybe they aren’t. Maybe we’d rather they weren’t.

But what’s true is that they’re laughing all the way to the bank.