Star stylist Kate Young is quick to correct when asked about the challenges of dressing clients for the awards season that runs from January through March.
“People think about awards season as five or six events that kick off in January, but it’s more like 20 events that start months before,” explains Young, whose clients include Rose Byrne, Dakota Johnson and Michelle Williams. “An awards season run can start with the film festivals in Venice and Toronto in September, and then in December you have the Gotham Awards, as well as L.A. and New York Film Critics. It’s so many award events and carpets, it can blow your mind.”
That plethora of red carpet events leading up to Sunday’s 2026 Oscars isn’t only about the quantity and quality of designer looks for high-profile stars. The job likewise can be rooted in a gradual succession of style notes that not only create an overall statement, they also play into the star’s personal preferences while feeling event-appropriate. And make no mistake: The Oscars isn’t only the climax of the awards season, it’s also the finale of the star-stylist dressing season, the ultimate style moment.
With that in mind, The Hollywood Reporter spoke with three top stylists, whose clients indeed will be on the red carpet Sunday at the Dolby Theatre at L.A.’s Ovation Hollywood, about navigating the season and the desire (or not) to create a style arc that will reach its crescendo at Oscars 2026.
Kate Young
Client: Rose Byrne, best actress nominee for If I Had Legs I’d Kick You
Rose Byrne at the 2026 Actor Awards.
Gilbert Flores/Variety/Getty Images
How would you describe your planning process?
I can plan the arc of the entire season in my head, but the reality is that early on you start to see what’s really working and how your client is responding. You’re also having an ongoing conversation about aesthetics: You put a client in a train, and she says, “I spent the whole night with people stepping on me,” so you know not to do that moving forward. So the season isn’t like a spreadsheet or notes; it’s all in my head and intuitive. I’m taking away from every event thoughts like, “This is working,” “This didn’t work,” or “Wow, she looks really great here.” And you carry all those thoughts through the rest of the season.
How do the Oscars differ for you versus the rest of the season?
For me, the Oscars are like a white-tie event or something on par with that, so it should be the most elevated dress and the highest high jewelry. Also, for all the previous events, they’re not always custom, but the Oscars is always a planned custom dress, the one you plan the longest and will get the most attention, so it has the most intention behind it. I’ve done vintage twice for the Oscars — a vintage Dior on Natalie Portman [in 2012] and vintage Mugler on Scarlett Johansson [in 2025] — but otherwise it’s always been custom. So you work with a house and early on give them notes: She likes a corset, she doesn’t like a corset, or here’s a color we haven’t done yet. I tend to have a silhouette in mind, and we can start that as the foundation of the dress and later think about details like an embroidery. It’s the best way to work with the time you have.
The Chanel dress that Rose Byrne wore to the Actor Awards, how did this design fit into your overall strategy?
I know people go all out and over the top for every event, but even though this dress wasn’t something I’d put her in for the Oscars, it was still a wonderful dress. It wasn’t only beautiful, she also was incredibly comfortable in it. I had to remind her, “Don’t look too comfortable,” because the construction was so light. There was nothing in there reminding her to walk like a movie star.
On Sunday night, how might we see all of these thoughts ultimately mesh in Rose’s look?
If you look at all the big awards shows, she wore Chanel to both the Golden Globes and the Actor Awards, and she wore Miu Miu to the BAFTAs. In all those cases, the dresses had a certain ease. So we’re going to try to elevate that, while also doing something that’s a bit more exciting.
Michael Fisher
Client: Ethan Hawke, best actor nominee for Blue Moon
Ethan Hawke at the 2026 Actor Awards.
Rodin Eckenroth/Getty Images
Prior to the start of an awards season, how do you develop a conversation about a client’s style on the carpet?
Regardless of an awards season, the way I like to work is that when a press tour starts, I will cast a wide net of requests to brands I feel would connect with the talent and/or the project. The brands that have been supportive from the beginning are usually the ones I’ll continue to reach out to and collaborate with — especially if the film or actor leads to an awards season. It’s important to continue relationships. It’s usually during the film’s initial press tour that a vocabulary develops. We get into a groove of what feels good, comfortable and feels the most authentic on the actor. But it’s business, after all, and brand partnerships do come into play.
Are you looking at the season as a whole or events individually, and is there a strategy of building upon each successive moment?
I like to treat carpets individually, but lean into the tropes that Ethan stands for — but I don’t like to jinx anything, so I really try to approach each carpet as if it’s the only carpet. Once brands submit sketches, I like to step back and look at the range over the course of the tour and slot appropriately and do what’s best for the show and the brands and, of course, the talent.
Does the arc of the season start out as, say, not as formal or detailed, and then you build from there?
There are many variables throughout the process. The Hollywood style machine is more complex than ever. So I try to keep a lens on the talent’s likes and dislikes and always put them first. Ultimately I am here for them and to help them present in the best way possible. I know what makes them feel good, confident and comfortable, and I lean into those, but always taking the talent’s temperature and listening to their feedback. So regardless, each carpet needs to feel good to my talent.
Many of Ethan’s looks this season have included wonderful details, such as the military-inspired vest [by Dior by Jonathan Anderson] that he wore to the Actor Awards. Are these details important to you both?
Yes. God is in the details. After all, actors are artists, and it’s fun to push authentic details when they are here for it, as Ethan always is! I have an art and photography background, so focusing on the right details gets them noticed and appreciated by the talent. It’s important to both of us, to keep it interesting.
What examples of your work from past awards season still resonate with you?
There are so many I really love, going way back to one of the first, in 2009 with Mickey Rourke. For the Oscars, we did an off-white and black Jean Paul Gaultier three-piece tux. From a design, fabric and construction perspective, it was truly inspiring and on point for Mickey. In 2017, Michael Shannon’s Oscars look when he was nominated for Nocturnal Animals was an immaculate Tom Ford double-breasted tux. It fit him perfectly and was a full-circle TF moment. Sebastian Stan’s tour last year was truly special, especially since he was a double nominee [for The Apprentice and A Different Man], starting with a custom Prada piped coat [for the Golden Globe Awards]. Then we turned up the classic leading man for the BAFTAs in P. Johnson, and then a completely different, yet more traditional Prada for the Oscars. The butter yellow pintucked shirt [with that suit] was unique and fresh for a spring carpet.
Do you consider the Oscars the ultimate moment of the season for you and your client?
It’s mainly because it’s the finale and it carries such weight, because there simply aren’t any more chances to celebrate the work.
Anastasia Walker
Client: Hudson Williams, first-time Oscars attendee
Hudson Williams at Gold House’s Lunar New Year Gold Celebration in February in New York.
Noam Galai/Getty Images
Because attention on both Hudson and Heated Rivalry just felt like it exploded following the show’s premiere last fall, was it an absolute thrill when you both found out he was invited to the Oscars this year?
Oh, absolutely. He’s been doing this a long time and is really talented, but to the rest of the world, this big blow-up of recognition has been in the last few months. So it’s not like other talent that has maybe experienced a slow build — he got a lot of attention when he attended the Golden Globe Awards, but the Oscars is such a different animal.
How are you approaching his look for Sunday night?
Nothing is bigger than the Oscars, so the main focus is that obviously it’s extremely formal. But we’re making sure we’re bridging the gap between that formality while also having a modern take on it. The clients I have who are attending are not your classic guys; they are really fashion-forward.
Who else will we see among your clients?
Shaboozey is also attending. He’s also a fun fashion guy. I am really lucky; all my boys are fashion boys. [Note: Shaboozey is performing alongside Buddy Guy, Eric Gales and others during a musical tribute to Sinners, which among its record-breaking 16 nominations includes a nod for best original song.]
Since Hudson does seem like he’s really into fashion, how do you approach his looks throughout the season?
As stylists, we are also working and coordinating with agents, and particular brand deals that they’ve arranged also may come into play. And sometimes there is a perception that if they are aligned with a brand, the brand will just be dressing them. I try to make sure I’m building good relationships with those teams as well, so that I’m able to insert a direction that we feel is right for that particular client. It might involve sending different mood boards back and forth versus what was originally presented, so that I’m advocating for this particular vision or idea that we want to convey. Thankfully, the teams we’ve had for brand partnerships have been so amazing and lovely and collaborative in that way. So you’ll see some things this weekend that represent that.
But we do put together some different things. We had a recent event where Hudson attended a Gold House party in New York, and Prabal Gurung was the host of that, so of course Hudson wore Prabal for that. We did play a bit with his suit, turning a belt into a neck sash and then using an earring on it so it looked like a brooch. He really likes to have fun with fashion, and that was reflective of that.
How do you approach the planning of the season overall?
Well, I’m a Virgo, so the love of organization is definitely there. We do a lot of planning, and if time permits, we’ll do custom. But sometimes we’re finding things out at the last minute, and we need four custom looks in a week and a half. You just have to roll with it and make it work.
What will be going through your mind when Hudson has finished dressing and is heading out to the red carpet?
Honestly, I’m still holding my breath at that point. I don’t breathe until I’ve seen it on camera and also know that the photos are good. Our agents are also on it; they’re watching the livestream and also looking at the photos coming in. Meanwhile, we’ve also checked the weather in advance — it’s supposed to be 88 or 90 degrees when the carpet opens, so I’ll be thinking about sweat. I’m always worried about sweat, but I’m also worried about how the jacket falls or whether someone will be on hand to make adjustments before he steps onto the carpet. So I’m always on edge until the very end.