The Oscars are top of mind as we move closer to February 26th. So from now until then, let’s do a few Oscar retrospectives, starting with Reese Witherspoon since 10 is a nice round number. And it was 10 years ago that she made her first appearance at the Oscars.

By far my favourite, favourite Reese Oscar dress. It was Valentino. The cap sleeves are gorgeous. Ava was 2 and a half. Deacon would be born the following year. Legally Blonde had just elevated her to major star status. Remember his quip on stage as they presented together? She makes more money, she can make the announcement. It foretold everything.

Word is she went to great lengths to secure this vintage Dior after finding it in a Paris boutique. That determination characterised her entire campaign. They pulled their sh-t together from the time Walk The Line hit theatres to the moment her name was called. After months and months of no family sightings, suddenly Reese and Ryan were the Team. Her jammed his tongue down her throat at the Golden Globes. She clenched her jaw and she went for the statue. Then... it was over.

Back at the Oscars as the reigning Best Actress and therefore a presenter, the newly single Reese made the rounds that season with a fringe in a series of amazing dresses, culminating in this custom Olivier Theyskens for Nina Ricci. I was there that year and remember seeing her on the carpet, hearing reporters shout her name for interviews, and witnessing firsthand the bitchface “as IF” in her eyes as she rejected them.

By the time she returned to the Oscars in 2009, she had a new boyfriend: Jake Gyllenhaal. But f-ck this was a terrible choice for her, non? It’s Rodarte, and on someone else...maybe. On Reese Witherspoon, it was a major mismatch. She and Jake showed up hand in hand at the Vanity Fair afterparty but broke up 6 months later.

I hated this Armani Prive. All of it. The styling, her hair, everything. Looking at it now it doesn’t offend me as much as it did initially but the Barbie effect, in service of promoting Water For Elephants, still doesn’t go down very smoothly. Reese married Jim Toth a month after the Oscars. Her wedding photos were (conveniently) published in PEOPLE just as press for Water For Elephants was building.

Is there another Oscar in her?

If she can find a role that is deserving of it, don’t be surprised if she brings along a baby bump.

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