Go big or go home: The biggest fashion mystery going into the ceremony is what designer Best Actress nominee Emma Stone will wear. Unlike many other big name stars, Stone is not affiliated with any one brand, making her a red carpet wild card. In the past, her stylist Petra Flannery has run the gamut in terms of designer credits—her La La Land promo tour alone saw Stone in Rodarte, Alexander McQueen, The Row, Valentino, Gucci and Prada, just to name a few. For her last Oscar nomination, in 2015 for Birdman, Stone and Flannery opted for a long-sleeved chartreuse Elie Saab gown covered in sequins. This year, Stone is favored to win and the fact that it’s likely her big night will no doubt be factored into dress decision-making. Like fellow redhead Julianne Moore, who went in a frontrunner in 2015 and came home with a Best Actress statue, I predict Stone will similarly win in custom Chanel—truly, the go big or go home of the fashion world. Expect to see her in some variation of Karl Lagerfeld’s silver sequined gowns with pink feather embellishments from the couture runway. – Lauren McCarthy, Digital Fashion News Editor
Dior’s Big Night: Since sending out her debut collection for Dior last October, Maria Grazia Chiuri’s sheer, corseted gowns have popped up on everyone from Bella Hadid to Sienna Miller. Since then, Chiuri has crafted an equally fantastical couture collection that has yet to make its proper red carpet debut. Expect faces of the brand Charlize Theron, a presenter, and Best Actress nominee Natalie Portman to be wearing custom versions of what we saw on the runway—and in the case of the very pregnant Portman, expect a chic-take on the empire waist. – L.M.
Fancy Pants: Pants have always had a real place on the red carpet—see Emma Stone’s Lanvin look at the 2015 Golden Globes and Emma Watson’s Christian Dior Couture at the show in 2014. But it's been Evan Rachel Wood who has made men's suiting fashionable on the red carpet again this season. Others are taking notice. Isabelle Huppert would kill it in an iconic ‘Le Smoking’ look, as would newcomer and fashion darling Ruth Negga. Perhaps this hot-off-the-runway fall silver lamé suit from Lady Gaga-favorite Brandon Maxwell might make an appearance on a swinging red carpet daredevil. – Caroline Grosso, Senior Digital Fashion Editor
Risky Business: Fashion with a capital F has been missing from awards shows' red carpets for some time, leaving the real fashion risk-takers to wear their wildest looks at an event like the Costume Institute's annual gala. I am hoping for a more ‘Wow’ moment at the Oscars this year. At the Golden Globes there were many liquid metal dresses, which always deserve a fashion gold star, but wouldn't be fabulous if actresses took their cues from couture? Rihanna once wowed at the 2015 Grammy awards in Giambattista Valli and I'll bet a small fortune someone—Tilda Swinton perhaps?—will wear Maison Margiela this Sunday and walk away a real fashion winner in lieu of an Oscar. – Courtney Costello, Fashion Market Assistant
Oscar's Oscar Debut: Yes, the Oscars may traditionally be Hollywood’s fanciest night out—read: full-length gowns only—but that doesn’t mean there isn’t some wiggle room. Kerry Washington opted for the shorter length in Dolce & Gabbana at the Golden Globes earlier this year, and with Fernando Garcia and Laura Kim’s outstanding options at Oscar de la Renta, we may see a few more dare to bare their ankles come Sunday. – L.M.
Red Hot: Valentino showed its Pre-Fall collection in New York earlier this year, and wowed with a series of beaded finale dresses that shined in the brightest stage lights. A perennial celebrity favorite—what goes better with a red carpet than Valentino red?— count on Valentino to make a cameo at this Sunday's awards, and perhaps this beauty of a red sequin, floor-grazing dress will come along for the ride. It’s a show-stopper! - Nora Milch, Senior Accessories Editor
Haute Romance: My two cents? We will see a shift toward the so-called New Romantics and a softer red carpet, both in fashion and in beauty, to go along with it. Consider the more bohemian look that we saw glimpses of at the Golden Globes, like Emma Stone’s loose hair and Michelle Williams’s off the shoulder A-line dress. Gone are the days of mermaid styles (I hope!) and in is the dawn of the new romantics that feel natural and chic, like Gucci. - Rickie De Sole, Fashion Market and Accessories Director
Looking Back: Who says jewels should be worn in the front? The trend in recent years seems to be baubles that showcase a delicate back, like Naomi Watts, who wore her Bulgari serpent necklace backwards on the red carpet at the Cannes Film Festival in 2014 and Jennifer Lawrence’s more simple Chopard diamonds-by-the-yard style necklace at the 2013 Academy Awards. Count on at least one statuesque stunner to take this risk on Sunday. — Grace Fuller, Jewelry Editor
The Naked Dress is Over: The sheer, “I can see your underwear” dress’ 15 minutes are up. Instead, expect stylists to turn to much more modern, streamlined silhouettes that feel a bit fresher, and certainly more covered up. This metallic number from Ralph Lauren’s Spring 2017 see-now-buy-now collection is a slinky upgrade that still has plenty of sex appeal. – L.M.
Mane Attraction: Nominees have been opting to decorate their hair with everything from jewelry to ribbons recently on the red carpet, just see Sienna Miller’s dainty hair bow at the Golden Globes, for instance. Now that the fall runway shows are in full swing, perhaps we’ll see some actresses take a note from Altuzarra and Tory Burch, where a bejeweled headband became the new bow. – C.G.