
Time Travel Back to the 2000 Premiere of 'How the Grinch Stole Christmas'
BY
Joan Summers | Dec 23, 2025

This was originally going to be a blog about the enduring yuletide fashions of How the Grinch Stole Christmas. What aspiring fashion journalist wasn't changed by Christine Baranski's landmark performance as Martha May Whovier? Then I saw the photos from the premiere.
On slightly chilly Wednesday in November 2000, various stars gathered in Universal City for the premiere of the live-action adaptation of Dr. Seuss' classic Christmas tale, starring Jim Carrey in prosthetics as the Grinch, and most importantly, Christine Baranski as love interest and iconic sex symbol Martha May Whovier, ensconced in a powdery blue coat I can almost touch, it's so vivid in the memory. The film's fashions have been much written about — particularly Baranski's wardrobe as Martha May. There was even a recent oral history in Vulture that was just about the best thing I've read all year. So color me surprised when I found very little on its premiere, or the emblematic turn of the century fashions.
From the vantage point of a post-Y2K boom and a full 25 years, the clothes worn on that fateful November eve sit at the crossroads of the waning '90s grunge sensibilities and the swift-approaching satin vibrancy of the early aughts. It's a confounding mishmash of denim and leather and trench coats and pops of pink and green that have utterly fascinated me.
I want to live inside this premiere forever, decked in sequins with my hair stacked to heaven. How funny, really, that the movie went on to become as popular as it did. I wonder if Melissa Joan Hart would have worn jeans again, knowing what a smash success it'd all be. Probably, if I think about it. Hilary Duff and her cohort of up-and-coming tween actors would continue wearing bedazzled tops and boot cut jeans to red carpet premieres well into the new millennium.

Among the iconic fits of the night was Baranski's, of course. The maven of Whoville wore her hair in the classic bob she'd become known for throughout much of her theater and Hollywood careers. The necklace and watch are classic Hollywood, in that these people absolutely dressed themselves and grabbed whatever it was they liked to wear. The real star here is this sequined dress, which looks like something my friends wore to prom. It's just so deliciously dated, from the column silhouette to the sweetheart neckline. It's something I'd imagine one of those TikTok fashion obsessives would style now with leather gloves and tabis for a quick jaunt on the subway.
Perhaps my favorite fit of the night is Rachel Leigh Cook's leather trench, plunging sweater and relaxed chinos. Her chunky leather platforms are also deliciously irreverent. More than any other outfit that night, this is the one I find to be the most contemporary and enduring, as I've pulled off the exact look perhaps ten different times this month alone.
Were it not for the pixie cut, this photo very well could have been taken today. It's what I find so charming about the millennium turn and the perennial staples of the cool girl — sometimes, the fits endure because they just work. Whether in 2000 or 2025, a leather trench and slacks can never go wrong.

Speaking of eternally cool girls, Courtney Love wore this daringly sexy knit dress to a children's movie premiere. She brought daughter Frances Bean to the premiere, which tracks, as does the tiny little purse and chipped red nail polish. It's almost like I'm looking at the face of my lifelong style icon. The wild hair really sells the look, as does the just-so-smudged pink lip and haphazard eyeshadow.

Over at the London premiere, future Gossip Girl star Taylor Momsen popped up in this delightful Mary Jane and caped jacket ensemble. I cannot overstate how delightfully cute this look is. Brings a smile to my face, really, to know Momsen was a lifelong style icon, future punk-pop career notwithstanding. Just look at these cute little shoes and the cut of this dress! Oh, my heart just explodes.

Back in Universal City, Melissa Joan Heart wore low-cut jeans and a sweater. The piecey hair and thin brows are exquisite, really, as are these thoroughly modern square cut booties. The chain choker is another favorite facet of this look, alongside the very-late '90s copper nail polish. I can still see the exact shade on my babysitters nails back in '99.

Speaking of copper nail polish, here's Molly Shannon in sateen pants with a front crease nobody ironed out and some biscuit kickers.The tube top is the real star, somehow, what with this bedazzled effect and the way it compliments the overwhelming brown of the look. I reference it near constantly, but I'm almost positive this is Mac lipliner in Twig. Ask me how I know!
And, because I must: "SUPERSTAR!"

The queen also made an appearance at the London premiere of the film in this minty gown and knit cape. The peep of silver from the heels is my favorite part, because I like to picture this little old lady thinking to herself: "Let's have some fun tonight, let's go for the silver kitten heels!" I wonder, though, what she thought of the love story between the beautiful Martha May and that dastardly Grinch with the fucked up body. Did it feel relatable at all to her, and what she'd put poor Diana through?

Kelly Preston is something of Seuss-head, seeing as she'd later star in The Cat in the Hat. She also starred in Jack Frost as a woman who'd maybe fuck a snowman that was also her reincarnated dead husband, if given the chance. How many other actresses can boast such career highs? I don't mean this as shade, being a Seuss diva and a Christmas diva is a rare honor, as is this outfit. From the pointy patent leather shoes with matching pants to the bucket bag and green suede trench, there's just too much to love here. The top is almost too much of a good thing, so much so that I have to keep scrolling up and making sure it's really real. Why don't tops these days come with beaded fringe anymore? I really think we should push mesh out of the conversation and bring back beaded fringe.
Regardless, there's just so many looks to look at. So why don't we send this post off into the Christmas night with a gallery of them? Merry Christmas all, but especially the attendees of the red carpet premiere of the 2000 holiday flick How the Grinch Stole Christmas!
Images via Getty