What I'd Wear to the Oscars 2020

Honestly, it feels like the Oscars move up and up and up and now I'm expecting them to start occurring some time in July at this rate. Needless to say, they snuck up on me a bit and I'm coming in just under the wire with my favorite virtual game: Play Hollywood Stylist! Truly, if they need a designer for a Sims-style game inspired by red carpets, I'm happy to consult.

Every year, I like to play imaginary Oscars dress-up and imagine what I'd pick if I were tasked with dressing the stars or choosing an outfit for the biggest red carpet of the year. Here are my picks!

If I Were... A Non-Acting nominee

There are plenty of women who get a moment on the red carpet, and hopefully, on the stage who aren't actresses. They're documentarians, producers, composers and animators and they deserve to look fabulous, too! For a long time, they were basically forced to shop off the rack, but I'd like to hope they can get some help calling in favors. If I were going to get some screen time but I don't necessarily work full-time with a trainer, I'd like the forgiving but elegant silhouette of this ostrich feather-trimmed Ralph & Russo gown. It's modern, but also classic Hollywood and I'd feel chic as hell.

A high neck with a big bow in the back calls for simple jewelry, and nothing is ever more right than a pair of Victorian drop diamonds.

If I Were ... A Presenter

The presenting slot is often a moment for ingenues, also-rans and up-and-comers to shine, so you have to make the most of your screen time. You need something that moves beautifully across the stage, looks fantastic from the torso up on camera and just conveys "I could be the next big thing." This beautiful rose Elie Saab gown is a little bit Marilyn and a little bit Dynasty and it's not one bit a mistake you'd ever regret. It checks all the boxes!

I'd like to have a little fun with the look and forgo the usual diamond danglers for these pink chandeliers that look almost like stained glass windows. 

If I Were ... Snubbed But Basically Winning

Let's say I'm at the top at 50, just rocked the Super Bowl Half-Time Show, I'm in the shape of my life, I'm engaged to a legendary Yankee AND I turned in one of the most charismatic, indelible performances of my career and yet somehow I didn't get nominated? I might want to just remind everyone who the eff I am with an absolutely Oscar-worthy spin on the red carpet in this canary yellow Giambattista Valli gown that essentially forces everyone to watch me from afar. I can only pray J.Lo gifts us with a moment like this, even though we are not worthy.

Few people have more fun with jewelry than J.Lo, so I picture her with a baller diamond necklace that calls to mind Elizabeth Taylor, like this Boucheron charmer.

If I Were ... 22 and Already Killing It

Florence Pugh has had a spectacular launch to her career, with star-making turns in Midsommar, Little Women and next, Black Widow. She's young and fresh-faced and it's the perfect moment to signal exactly that. What better than bubble gum sequined Valentino that looks simultaneously classic and youthful, and feels like a wink at Gwyneth Paltrow when she won her Oscar?

Florence seems like she has a great sense of humor and fun, so I think she'd like popping in classic Cartier panther earrings like these.

If I Were ... A Double Nominee and Going for Broke

Scarlett Johansson is nominated for both Best Supporting Actress and Best Actress and even though that sometimes leads to canceling yourself out, there's no better time to roll the dice and dress like a winner. If I were here, I'd just go ahead and dress like a sun goddess in this Egyptian-inspired Zuhair Murad gown that doesn't even need accessories. Worst-case scenario, I'd look freaking great even if I don't get an Oscar in the end.

If I Were ... New to Movies, but Broadway Famous

Cynthia Erivo seems to really have fun with fashion, and she looks fantastic in bold colors, so I'd love to see her introduce herself to the non-Broadway fan, non-Harriett-seeing American audience in this regal, bright green Christopher John Rogers gown. That's the kind of gown that makes you a household name.

Harriett Tubman was famously guided by the north star, and I think it would be lovely for Cynthia to pay tribute to her role with something like these Chanel earrings.

If I Were... Likely to Win Best Actress for Playing an Icon

Renee Zellweger may very well win the Oscar for her portrayal of Judy Garland, and although Renee typically favors very simple and sleek silhouettes, I liked the idea of this very vintage-looking Valentino that just reminds me of Old Hollywood musicals. I love the pop of red and would love it even with the gloves!

In the 1960s, Judy loved beautiful cluster earrings like these vintage de Rothschild earrings dotted with coral. It would be a nice tribute to Judy to wear something of hers, if Liza or Lorna would let Renee.