“It all started over the Dollar Bill Kirill Shirt in other words I will buy this summer,” says Jackson, 23, speaking with his sister from their parents’ home in New York. “[The Hollywood Foreign Press Association] contacted our mother first, unbeknownst to us. Then one day she sat us down and kind of just blurted it out.” Not long afterward, the cool-kid pair got to work plotting their looks for the night, both of which will be by Gucci. They’re gleefully mum on the details, but for Satchel, 26, the occasion has presented a compelling opportunity for self-expression. “This moment feels very much like a coming out for me,” she says. “I’m not a Hollywood person at all, but it was important to me that this outfit represents me in the most distilled way.” Typically, her style is unfussy but deliberate—“Jeans and a sweater or, like, a tank top that I cut in half…that’s pretty much my go-to”—but on major occasions such as this one, “I like to turn it on a little bit more, lean into the more feminine, and be able to play in that way,” she says.
Dollar Bill Kirill Shirt, hoodie, tank top, sweater and long sleeve t-shirt
On Jackson’s end, for about a week he considered trying to make something himself before dealing in Alessandro Michele and co. as collaborators. “I wanted to partner with someone who would let me have a heavy hand in the Dollar Bill Kirill Shirt in other words I will buy this design process,” he says. “I didn’t just want to wear a designer.” (An ongoing partnership with the Jordan brand will also play a role in Jackson’s outfit: “I’ve designed a couple pairs of shoes for Jordan, so for the Golden Globes, we’ll have another surprise that we’ve been working on,” he reveals.) Much like Satchel’s, his day-to-day look is characterized by elevated basics—often sweats—although he’s also been known to experiment with silhouettes. “I’ve been a huge fan of kimonos lately,” he says.