The Red Carpet Trend Stylist Jason Bolden Predicts Will Dominate This Year’s Oscars

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If award season was a sport, Jason Bolden would make the red carpet fashion all-star team. The in-demand celebrity stylist and star of Netflix’s Styling Hollywood has been responsible for some of the most memorable looks of year thus far. So, if you’re looking for credible expert predictions for the 2020 red carpet fashion trends to expect at the upcoming 92nd Academy Awards, he’s your man.

Indeed, 2020 has already proven a major year for the Los Angeles-based stylist. His client, actor Cynthia Erivo, was nominated for multiple awards this season for her role in Harriet (including the Academy Award for Best Actress). The new darling of the red carpet, Erivo topped best dressed lists all last month, including the Golden Globes, where she wore a sparkling fitted black and white Thom Browne gown and the SAG Awards in which she arrived in a breathtaking two-toned custom Schiaparelli masterpiece.

Bolden was also responsible for Alicia Keys' multiple outfits while hosting the 2020 Grammy awards, including the stunning one-shoulder silver Versace gown she donned as she opened the show. And his list of A-list clients goes on: Ava DuVernay, Taraji P. Henson, and Yara Shahidi all go to the veteran style expert for a standout red carpet moment. And he delivers.

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Considering his front-row seat to the marathon that is award season, it's not surprising Bolden has opinions on what to expect for the upcoming Oscars. “I think the silhouettes are going to be a bit more column-like and the colors are going to be really bold,” says Bolden on a phone call facilitated by Invisalign. Indeed, the latter forecast has already been executed with gusto this year, as hues like tangerine, ruby red, lilac, and fuchsia have dominated the carpets of this season's Golden Globes, SAG Awards, and the most recent BAFTAs. However, considering the dramatic return of the princess gown, Bolden’s call out for column dresses would be an interesting (and welcome) nod to Old Hollywood glam at the Oscars.


Taking the above information into consideration, there are some clear contenders from the recent runways that could make for unforgettable style moments at the Feb. 9 event. For instance, Valentino's Spring 2020 Couture collection featured a candy-colored melange of worthy options, including a stunning color-blocked mermaid style (worn by Kaia Gerber on the runway), with a trifecta of white, pink, and red hues and a fitted corset bodice. Also embracing color this season is Ralph & Russo, whose ethereal collection featured a stream of chartreuse dresses that would definitely turn heads at any awards show.

As for emerging designers worth watching, Bolden says he's been keeping close tabs on Charles Harbison, whose gender-neutral pieces have been seen on the likes of Michelle Obama and Beyoncé. (Bolden actually selected the emerging talent for DuVernay's look for last year's Vanity Fair Oscar Party.) "He's a pretty quiet designer, but I'm always excited to see what he has coming," says the stylist.

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Now, anyone who's seen Bolden's Netflix reality show (which documents his day-to-day life as a celebrity stylist) knows plenty can go awry when dealing with extravagant designer gowns and high-profile events and talent. Loose or broken straps, overtly sheer fabrics, accidental stains, too-big shoes — all are part and parcel of the whirlwind that is award season, and can take an ensemble from pure perfection to total catastrophe.

When asked about said snafus and possible style roadblocks Bolden lightheartedly shrugs off the notion, insisting nothing is unfixable — if you’re prepared. “Always prepare with undergarments,” instructs Bolden. “Also, I travel with loads of inserts for shoes, a lot of double-side tape which is always a saving grace, and the oldie but a goodie ... a sewing kit. I advise everyone to ask for a sewing kit the next time you’re staying in a hotel, and keep it with you everywhere. I’ve literally had to stitch myself back together at events before. These are the types of things that I always think about.” And now, it's safe to say assume everyone else will, too.