Jason Bolden makes red carpet moments. Period. Although, we know you’re already well aware of this given that he’s probably created some of your favorite recent looks for his roster of A-listers including Alicia Keys, Yara Shahidi, Ava DuVernay, and Cynthia Erivo, to name a few. And while award season is arguably one of the busiest times of his year, the stylist and star of Netflix’s Styling Hollywood found a few spare moments to sit down with us as part of his partnership with Invisalign to chat about some of his Oscars red carpet predictions.
Ahead, we’re sharing three of the trends (complete with visual inspo from celebs he works with RN) that he thinks will dominate the carpet this season. Interestingly enough, while celeb-approved, all of the trends in question are actually quite relatable and could work for your own events and parties, so naturally, we’re showcasing how to shop each of Bolden’s trend predictions as well.
But we didn’t stop there. Given that Bolden is styling the brilliant Harriet actress Cynthia Erivo, a nominee for best actress, we also wanted to sneak in a few questions about how he created her joyful fashion narrative throughout her recent red carpet takeover.
Keep scrolling for a glimpse inside the mind of one of Hollywood’s creative powerhouses.
1. Strapless and Slit Dresses
Yara Shahidi in Carolina Herrera
“I think there’s going to be a lot of skin—a lot of these beautiful, column, old-school silhouettes. Like strapless and slits up the back.”
“I think we’re going to see that classic sandal—a strap across the toe, a strap around the ankle. It’s so sleek, so easy, and it works with everything. Also, like the classic Manolo Blahnik pump. We all love the one that Carrie Bradshaw wore all the time, and I think that kind of moment is so classic and so easy that it just works. Nothing is sleeker or cooler than a super-high pump.”
“Hopefully there are going to be major jewelry moments because what we’ve seen so far on the other carpets is that everyone has been kind of sleek and easy, but the pop of magic has been people’s jewelry, so I want to see big queen jewels—like the biggest ones.”
How did you and Cynthia approach the overall fashion narrative for this season?
I’ve only been with Cynthia for four months, which was the start of the press tour for Harriet. We were shooting the cover of a magazine and met that way, and I had an idea of how I wanted the cover to look, and then once we went into the idea of me being her personal stylist, I kind of really leaned into the idea of Cynthia coming from theater. She adores fashion. I’ve never met someone who actually wants to own the most uncomfortable, awkward, hardest things to wear. She actually wants to own them. I tied that into the strength and the ambition that both Cynthia and Harriet have, and what she conveyed in the film. So we really started there and wanted every time that we stepped on a carpet or stepped in front of a screen to give this impactful, sensational fashion moment to honor Harriet and be in this space where we would always laugh and say, If Harriet was going to this, we would probably want her to wear this.
From all the pain and the hurt that people of color have had and have to go through, we decided to make everything feel so light and so happy—we just wanted to smile. That’s the thing that everyone has leaned into with Cynthia because, versus a lot of people, when they do the red carpet, they take it so seriously and their faces are so stoic. Cynthia is literally having the best time. Her best accessory, clearly we go back and forth, is her smile. We lean into that. Every time she walks onto the red carpet, it’s like you are watching a feel-good movie.
What does she tend to gravitate toward?
I’m very lucky when it comes to the things Cynthia leans toward. At this point, I know her. I know when I go look at a collection, I need to go look at the hardest look that will translate in real life. For example, the Marc Jacobs dress that she wore to the L.A. premiere of Harriet, it’s one of those looks that looked so fantastic on the runway, but will that translate in real life? If a photographer shoots it, they can manipulate the shoots beautifully, but for Cynthia, it’s like you have to have that balance for her because she wants the hardest, the strongest, the boldest thing that walked, and our fittings are based around that. So when that Marc Jacobs dress came in, we put it on, and she was like, “This is it!” When she put the Valentino Couture on, the train was as long as Princess Diana’s, that worked! She is the perfect muse for designers because real creatives want to see those interesting hard pieces on real-life people.
What look, leading up to the Oscars, really stands out and is the most memorable for you?
With Cynthia, I think it would be, ah man. I think it’s the Fendi Couture look for the Critics’ Choice Awards. Cynthia had 15 minutes, and we had to fit for 10 looks, and that was one of the dresses that was on the rack. And I said to her, this is my dream dress. I want you to wear my dream dress for me. I received it from Milan, and I held it, and it was one of those moments where I was like I’m holding this because I know this dress needs a moment. Cynthia tried it on, it needed no alterations, she let me take a photo, and she ran out of the house to go to a rehearsal for something. For me, it’s the most impactful because it just shows the ease of how it really should be. And when you think about things you love, when you think about fashion, it should feel easy, it should feel light, and it should feel like your own. That look felt like Cynthia; it literally felt like that dress loved to be on her as much as she loved to be in it.
Can you give us any details around her Oscars look?
It’s magical. I have goosebumps; it’s magical. I literally went through… I waited for the couture collections to walk, and I had sketches, and then I saw it and I was like that’s it, that’s the dress. She still hasn’t tried it on, so I don’t know, but my hopes and dreams are that is the dress.
And finally, as you mentioned, it's sometimes all about the smile. How did your recent partnership with Invisalign come about?
To be completely honest, I always had a really tiny gap, which was kind of like a family gap. I always loved it and never really thought twice about it until one day I decided I wanted to brighten my smile and I wanted a perfect smile. And I decided to go in and do the Invisalign treatment, and it literally changed my life. I thought everyone would go crazy for my Netflix show about the talent that was on my show, but everybody is like, “Oh my God, Jason, it’s your smile! We love it! We love when you post to your Instagram and you’re smiling and having a good time.”