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The Grammy Awards are coming up this weekend, which my children have been reminding me of for quite some time now. I'm more excited about the Grammys this year than I am most years, because my kids have been spending time "educating" me on their favorite artists, which means I actually recognize the majority of the nominees this year. That doesn't change the fact, however, that I am still more interested in what everyone will be wearing than in the actual bestowing of awards. So I thought it might be fun to look at some of the best and worst red carpet looks that the nominees (in selected categories, plus a couple of requests from my kids) have worn at various red carpet events in recent years.
And the nominees are...
Bad Bunny (Record of the Year, Album of the Year, Song of the Year)
Best: 2024 Academy Awards
Bunny presented an award wearing a classic black double-breasted tuxedo with a high closure, worn shirtless, accessorized with a chunky diamond necklace.
Worst: 2025 Happy Gilmore 2 Premiere
The plaid jacket may have been a nod to the film - and, to be fair, it's perfectly fine by itself. But combining it with chevron-patterned shorts that look like boxer shorts, elastic-strap black ballet flats with white crew socks, and a flat-brimmed baseball hat was not a good look.
Sabrina Carpenter (Record of the Year, Album of the Year, Song of the Year, Best Pop Solo Performance, Best Pop Vocal Album)
Best: 2024 VMAs
Carpenter has plenty of gorgeous red carpet looks, but this strapless figure-hugging silver vintage Bob Mackie gown is one of the best. It's sexy without being overly revealing and has an air of Old Hollywood glamour without looking dated.
Worst: 2022 American Music Awards
"Worst" is a relative term here, because this look really isn't all that bad. It's just not a good cut for her slender-but-straight figure. The horizontal lines of both the bandeau-style top and the short, straight skirt make her body look very rectangular.
Doechii (Record of the Year, Song of the Year)
This stunningly pleated structural design was an eye-catching color and style, and I love the way her asymmetrical hairstyle echoed the lines of the gown.
Worst: 2025 Grammy Awards
I actually love the top of this Thom Browne ensemble, with its whimsical take on menswear in the form of a strapless vest made of a pair of cuffed dress pants wrapped around the waist, but the weirdly puffy skirt was too layered, too bulky, and too disjointed.
Billie Eilish (Record of the Year, Song of the Year)
This Bridgerton-inspired custom Gucci gown was an unexpected choice, but I loved the way Eilish made it her own with a black choker and black feathered headpiece, and the lace gauntlet-style sleeves were very "her."
Worst: 2024 Golden Globes
Although the concept was fine, the hugely oversized jacket designed by Willy Chavarria looked uncomfortable, like a little kid wearing her father's clothes, and the pink ankle-length ruffled socks were just weird.
Lady Gaga (Record of the Year, Album of the Year, Song of the Year, Best Pop Solo Performance, Best Pop Vocal Album)
Best: 2019 Golden Globes
This periwinkle Valentino Haute Couture ballgown was simply breathtaking. I loved her matching lavender hair, and that diamond necklace was to DIE for. The puffed floating sleeves and long ruffled train were just offbeat enough to suit her style without losing the glamorous look.
Worst: 2015 Academy Awards
It was bad enough that the top of the Azzedine Alaïa-designed gown looked like an old-fashioned full coverage apron with side ruffles, but then she accessorized it with flared red gloves that looked like rubber kitchen gloves.
Kendrick Lamar (Record of the Year, Album of the Year, Song of the Year)
This slick blue suit featured barely pegged pants, a narrow satin collar, and a narrow black panel at one side of the jacket front, worn over a black satin tee. It was classy but just a little different.
Worst: 2025 Grammy Awards
This custom Maison Margiela "Canadian Tuxedo" was simply baggy jeans, a denim jacket over a white t-shirt, and a denim cap. Zero effort was made here.
Best: 2022 Grammy Awards
Sza stunned in a body-hugging Jean Paul Gaultier tan tulle gown with a long train, embellished with colorful fabric flowers running down the front.
Worst: 2024 Grammy Awards
While SZA did not walk the red carpet at this event, this Do Long gown did appear publicly on stage when she won, and it was ugly enough to land here. The lines of the gown, especially the gathering at the hips, was quite lovely, but the sheer front had oddly-placed opaque areas and looked unbalanced and awkward.
Chappell Roan (Record of the Year, Best Pop Solo Performance)
Roan paired a vintage rhinestone top she found on eBay with a rhinestone-embedded showgirl headpiece with hanging crystals and a lampshade-shaped newspaper-strip skirt designed by Efrain Nava and Manny Robertson. It was wild and crazy and fun, and I found it to be both a lovely tribute to Cyndi Lauper (who was presented for induction by Roan) and unique to Roan's own personal style.
Worst: 2024 Guts World Tour Movie Premiere
This sheer Harper Collective design had oddly-placed oversized flowers down the front of the bodice and carwash panel skirt, and an ugly granny panty underneath, although I did like the gauntlets with smaller matching flowers on the back of her hands. The black boots were the wrong choice for footwear, though.
ROSÉ (Record of the Year, Song of the Year)
This gold and silver Oscar de la Renta design featured a straight-across strapless bodice and a straight skirt consisting of fringe from mid-thigh to floor. The metallic silver caught the light beautifully, especially with the movement of the fringe.
Worst: 2022 LACMA Art+Film Gala
I struggled to find a bad red carpet look for her, and the closest I could come was this hooded Anthony Vaccarello for Saint Laurent. It's not bad, except that the low bodice and high neckband and hood are both a major contrast in style and create visual weight well away from her face.
Bruno Mars (Record of the Year, Song of the Year)
Best: 2025 Grammy Awards
Mars looked cover model-worthy in a sleek double-breasted charcoal grey silk satin Saint Laurent tuxedo, worn shirtless with Tiffany jewelry and dark sunglasses.
Worst: 2018 Grammy Awards
I had to go all the way back to 2018 to find a red carpet misstep, and even so, Mars didn't technically walk the red carpet at this event. It's not bad, pairing black jeans and a white t-shirt with a red sequin zip-front baseball-style jacket, it's just kind of...meh.
Justin Bieber (Album of the Year, Best Pop Solo Performance, Best Pop Vocal Album)
Best: 2021 Met Gala
This elegant shiny black wide-legged Drew House tuxedo featuring a cropped jacket was unfortunately worn with embellished white tennis shoes, but the bonus points for the French cuffs cancelled them out for an overall good look.
Worst: 2022 Grammy Awards
This oversized Balenciaga suit was ill-fitting and ugly by itself, but was made even worse when accessorized with a bright pink knit beanie and [shudder] oversized Balenciaga Crocs.
Clipse (Pusha T and Malice) (Album of the Year)
Best: 2025 GC's Men of the Year
Worst: 2025 ESPY Awards
These outfits weren't terrible, but they were too casual for the red carpet (even at the ESPYs). They somehow managed to come off as both boring (due to the cut and color) and also hard on the eyes (due to the multiple sizes of squares on Malice's jacket).
Leon Thomas (Album of the Year)
Best: 2025 BET Awards
The custom suit designed by Rey Jaiteh included a few subtle but fabulous details, like grommetted lacing at the shoulders, matching grommets below the jacket pockets, and a pearl beaded watch fob.
Worst: 2025 MTV Video Music Awards
Not terrible, but the combination of a shapeless double-breasted wool overcoat and a satin print bandana was not red carpet worthy.
Tyler, The Creator (Album of the Year)
Best: 2020 Grammys
Inspired by the film The Grand Budapest Hotel, the pale pink bellhop uniform (custom designed by his own brand, Golf le Fleur) was crisply tailored and whimsical, but the best part was that he wore the striped shirt that was in the suitcase later in the show.
Worst: 2021 BET Hip Hop Awards
Another Golf le Fleur design, the ivory satin shirt with peach collar looked very feminine, and simply didn't go well with either the cropped brown paints or the fur hat. None of the pieces were bad by themselves, they just didn't belong together in the same outfit.
EJAE (Song of the Year)
Best:2026 Golden Globes
This simple strapless black lace Dior gown featured semi-sheer vertical panels in the skirt and was accessorized with a high geometric updo and a single curved tendril framing her face.
Worst: 2025 MTV Video Music Awards
This look wasn't terrible, but the wide-legged trousers and bulky jacket overwhelmed her petite frame, and the red-edged leather...tree branch? lobster claw? across the bandeau wasn't interesting enough to make it memorable.
Audrey Nuna (Song of the Year)
Best: 2025 "A Year in TIME"
Nuna usually opts for avant garde looks on the red carpet (with varying levels of success IMHO), but I liked the lines and print of this simple one-shouldered black-and-white silk Moschino column with multiple oversized bows.
Worst: 2026 Golden Globes
This Thom Browne ensemble was a LOT of look, with white bows at the neck and ankles forming the body of the dress into a constricting barrel shape, plus an intricate braided hairstyle under a birdcage veil, plus stylized black lipstick. It was just much too much.
Rei Ami (Song of the Year)
Best: 2026 Golden Globes
The black lace custom Valdin Sahini gown featured sparkly beading on the skirt and tiny angled straps, and it fit her like a glove. Ooh la la!
Worst: 2025 MTV Video Music Awards
Billed as a "mixed-media punk look" that included pieces by designers Seks Dolls, Diesel, and Vivienne Westwood, the ensemble combined a low-slung fringed black leather microminiskirt, pointy-toed multi-buckled black stiletto boots, and a black motorcycle jacket, then topped it all off with a fluffy burgundy wrap/vest/sweater thing. No, honey. Just, no.
Lola Young (Best Pop Solo Performance)
Best: 2025 BRIT Awards
Although I'm not a huge fan of the baggy, bulky, unevenly cuffed jeans, the soft shirring of the white satin peasant blouse and the sheen of the silvery-green soft velvet ruched cropped jacket are absolutely fantastic, and I love her multi-colored hair and super-feminine makeup.
Worst: 2022 BRIT Awards
Everything here is fine in concept but wrong in execution. The texture of the alligator jacket is weirdly casual over the hyper-sexy sheer top (which isn't doing her figure any favors), and the flared ankle pants are too wide and too short with this outfit. It just can't figure out what it's trying to be.
Miley Cyrus (Best Pop Vocal Album)
Best: 2025 Golden Globes
This Celine by Hedi Slimane black column with crystal-edged, star-shaped front cutouts was surprisingly demure, as was her shaggy updo. It was a great balance of elegance and edginess.
Worst: 2024 Grammy Awards
Designed by John Galliano for Maison Margiela, this gown (what there was of it) was made from 14,000 safety pins forming a mostly-sheer gown. The concept was fascinated but the crotch tassel and the humongous frosted '80s hair lost it for me.
Teddy Swims (Best Pop Vocal Album)
Best: 2025 Grammy Awards
Not only did I love the three-piece champagne-colored satin suit, but I loved that it was encrusted with pearls in honor of the upcoming birth of his first child, whose birthstone would be pearl. Awww!!
Worst: 2025 Brit Awards
I understand that this long coat covered with stuffed animals was meant to be a nod to the outfit worn by Rachel Berry (Lea Michele) on Glee, but it was just weird and uncomfortable.
JID (Best Rap Album, Best Melodic Rap Performance)
Best: 2022 American Music Awards
The wide, straight leg pants and the slightly nipped-in-at-the-waist jacket with its trailing ribbons made for a great silhouette. I liked that there was a subtle hint of straightjacket in the top, which gave it an edge without being too over the top.
Worst: 2017 BET Awards
My son informs me that JID had barely started his career when these awards happened, so he probably just threw on whatever clean shirt was in his closet. But that shirt shouldn't even have been in his closet, never mind on the red carpet.
Kehlani (Best R&B Performance, Best R&B Song)
Best: 2025 Grammy Awards
With pinstripes emphasizing its geometric structure, this Robert Wun gown featured a sweetheart neckline, a criss-cross peplum, a short train, and a narrow front panel with four buttons reminiscent of a double-breasted suit jacket. Charming!
Worst: 2025 BET Awards
Not a terrible dress (it's an Archival Dior by John Galliano, after all), but the color and texture blends oddly into her tattoos, the bodice has a kind of "shelf" effect going on, the hem is oddly short, and the straps are so wide-set that they look like they're about to fall off her shoulders.
Jennifer Simard (Best Musical Theater Album)
Best: 2022 Tony Awards
This striking custom Peter Langner gown was all about textures and lines, with pale champagne tulle shot through with metallic gold creating a fringe-like effect in the full skirt and emphasizing the waist of the snug-fitting bodice, which was topped with a pleated ruffle.
Worst: 2022 Drama League Awards
"Worst" in this case is more like "least best," because I really didn't find any red carpet looks from her that I truly disliked. My biggest objection to this look is that it's overly casual for a red carpet, and the bodice seems to be a bit tight and is not flattering on her fabulous figure. But it's a cute dress and I would absolutely wear it myself!
And now we all just need to wait until Sunday to see if anyone will wear such a great look that they'll have a new "Best" on this list - or maybe such a bad one that they have a new "Worst"!
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