Rihanna and Rocky: Tailored to Trial

Courtroom fashion is not a recent preoccupation. For starters, it’s about presentation and respect for the court. Even regular degulars are told by their lawyers to be mindful of what they wear for trial. Conversations, then, about courtroom fashion aren’t new. They were happening in all the mob trials in the 80s in New York. They were happening over 20 years ago, back in 2002, when Winona Ryder was on trial and the Washington Post covered her trial style. "She may be a shoplifter, but she has impeccable taste" is just one of quotes from that piece. 

Remember the headband and this gorgeous coat? 

“Very demure, very mindful” might have popped in 2024 but Winona Ryder was serving it in court! 

The headband was its own character. But look at that pretty collar! 

What’s more demure and mindful than a cardigan and florals!?

Seriously, almost all of these looks would play today – demure and mindful and classic. 

This belted blazer? COME ON!

Sorry, I got sidetracked by my beloved, but I think you get the point. And just in case you don’t, scammer Anna Sorokin had a fashion strategy (and an Instagram account documenting it!) and Luigi Mangione’s courtroom sweater sent the internet into a meltdown.

But the new fashion king of the courtroom is now A$AP Rocky. The suits and trenches were gorgeous, the details were exquisite – neckties and scarves and crispy shirts and shiny shoes, not a single wrinkle or fold. By now I think we can all agree, clothing is expression, extension, and sometimes armour. Rocky’s stylist, Matthew Henson, told GQ that for Rocky, his trial wardrobe wasn’t just a flex, it was for comfort and confidence. When you’re facing that may years in prison, you want your clothing to give you hope, and to convey to the jury that you’re worth the hope and faith they might put in you if they acquit. 

Rocky’s trial style has become an obsession for fashion watchers. This is not surprising given Rocky’s reputation as one of the most stylish celebrities of his time. But even by his standards this was a new level. Several designers and fashion houses were represented but the most prominent was Saint Laurent, to the point where the Saint Laurent comms team sent out near daily press notes about his looks, without mentioning the trial, just that Rocky was “seen in Los Angeles” in the Saint Laurent xyz whatever. 

Suiting has been Saint Laurent and Anthony Vaccarello’s super power for the last year and a half or so, with his two most recent collections, for men and women, described as a “master class” and hailed as one of the strongest showcases in years. And the timing couldn’t be better. Because Rocky is one of the co-chairs of the Met Gala in May. The theme? “Superfine: Tailoring Black Style.” So Rocky just got the jump on everyone else. 

And with Rihanna, it’s a one-two punch. Because she’s also been suited and booted lately. Last night, for her birthday dinner, menswear was her mood. Conveniently, seeing as Rihanna, the icon, is leaning into this suited moment, Saint Laurent is capitalising, too, posting two new shots that pretty much cap off their big week, considering that Rocky and RiRi have been making so many headlines, and the brand has been mentioned so much. 

You know who was ready for this? Nicole Kidman, of course, thanks to Jason Bolden. Remember that suit at the Critics Choice Awards? This bitch in that f-cking suit!

Attached - Rocky in a selection of outfits over the last few weeks, and RiRi and Rocky celebrating her birthday last night in LA.