The True Story of Celebrity Oscar Dresses - Rules Politics and Why They Wear What They Are Wearing

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The question “Who are you wearing” is a loaded one in Hollywood. It’s a phrase that can elicit cringes in even the most poker-faced red carpet attendee. It’s a phrase that can spark hundreds of reactionary tweets. Asking an Oscar attendee to identify the designer of her dress is an act that can seem trivial in a time of heightened awareness and attention to inclusion and equality (and, let’s not forget, the movement to #AskHerMore), but it actually has a long and important history of necessity in the award show system.

That’s because the tradition of dressing an actress for an award show, like almost anything in the industry, is truly a business opportunity.

Fashion designers, actresses, and their stylists are all furiously prepare for what is to be one of their collectively most pivotal moments of the entire gold statue rat race: The red carpet. Viewers may be tuning in to find out who brought their mom as a date or whether Amy Schumer is going to shout out O.B. Tampons again, but there’s a behind-the-scenes system that’s banking everything on those few minutes of screen time.

This, ladies and gentleman, is the story of celebrity Oscar dresses.

It’s a long process that can take up all of an actress or stylist’s free time, but the first rule of thumb is to never start too early—that’s called jinxing it. Once the nominations are announced, however, it’s go time, and so begins the act of trying on dozens of dresses (stylists cop to overseeing as their clients try on upwards of 50 dresses before they choose The One.)

There are, basically, two options for an actress attending the Oscars: They can choose to borrow from a designer’s new collection, or have something custom-made for them by a designer. (Technically they could also purchase their own gown, but paying for it yourself isn’t nearly as fun.) There are myriad reasons why it’s simply assumed that celebrities will get free clothes for award season, but the short answer is that having an Oscar nominee (or even Oscar winner) wear, and talk about, your dress on the year’s biggest red carpet is simply great PR. And fairly easy PR at that.

A custom frock is kind of the Big Kahuna of award season, and it’s an opportunity that doesn’t come around very often. As Aliza Licht formerly DKNY PR Girl, told E! News a few seasons ago, having a one-of-a-kind gown is a major selling point, both for the stylist and the actress she’s working with, as well as the designer who’s hoping to bolster their brand.

“There will be a conscious decision to not show that dress on a the runway,” she said of the top-secret process. “So, if you are a stylist [with a client receiving one of said dresses] you’ll get sketches beforehand, but never photos. We want it to be special.”

If an actress is choosing from a designer’s collection, then the actresses who are nominated often get first dibs, followed by the show’s presenters. Obviously, each sample can only be worn by one person—and each star needs to wear a different dress, especially in the Internet age of instant duplicate spotting—so things can get a little competitive. Said Licht, “Often, it becomes this calendar of fittings. If we think one celeb will look better in a certain dress than one of the other celebs requesting that dress, we can hold off.”

The result is a true organizational mix-and-match, in which stylists attempt to narrow down a partnership between a designer who’s interested in dressing a certain actress, and an actress who’s interested in wearing a certain designer. Say Louis Vuitton wants to dress Alicia Vikander, but Alicia has her heart set on a Calvin Klein gown, but Calvin Klein wants to dress Brie Larson …it all just shuffles around until everyone’s happy.