Great Outfits in Fashion History: Britney Spears at the 2000 Grammy Awards

This seemed like the end-all, be-all of grown-up dressing at the time.

Britney Spears in a Randolph Duke gown and Oscar de la Renta stole.

There are perfectly good celebrity style moments, and then there are the looks that really stick with you, the ones you try desperately to recreate at home. In ‘Great Outfits in Fashion History,’ Fashionista editors are revisiting their all-time favorite lewks.

Frankly, as far as I was concerned, there was no one — and I mean no one — more important in the year 2000 than one Miss Britney Spears. She was a bright, bubbly blonde superstar just a few years older than I was, and I wanted nothing more than to emulate her every move.

A lot has happened to Spears, me and hell, all of us in the 20 years (I’m sorry that’s just a fact) since the new millennium hit. I can no longer say I try to copy her every move. But there are a few things about Spears which still stick for me: her sparkling spirit, her borderline socialist social media postings and this incredibly glamorous look from the 2000 Grammy Awards.

Spears was nominated — and subsequently robbed — in the categories of Best New Artist and Best Female Pop Performance for “…Baby One More Time” that night. But no one can ever take away how incredible she looked on the red carpet. In a time when the fanciest thing I wore was a black, glitter-covered dress from Delia’s, this white Randolph Duke gown seemed like the end-all, be-all of grown-up dressing. She even paired it with a white fur stole from Oscar de la Renta and a diamond necklace! And while the look is Old Hollywood glam, Spears kept things distinctly Y2K with her flat-ironed hair and mocha-brown lips. To die.

I still don’t have many occasions to get dolled up in a full-length gown, but what I am going to copy ASAP is the look Spears wore to a pre-Grammy party that same weekend: a megawatt tank and feathered mules, pictured below.

Britney Spears attends the 2000 Arista Records Pre-Grammy Party.

I’ll be swapping the extreme low-rise pants for high-waisted denim and ditching the sheer wrap altogether — but honestly, that baby blue eyeshadow is looking really tempting.

Shop Spears-inspired items in the gallery below: