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The Emmy Awards happen each year, and before the trophies for TV are handed out, style obsessives tune into the infamous red carpet to crown winners in a different category. Looking back, some dresses have left us swooning, but there’s also been no shortage of celebrity red carpet outfits that went off the rails. Our favorite small screen stars have offered up some big fashion flops, and so we need to discuss the worst-dressed celebs in Emmys history, some of which date all the way back to the ’80s.
No knock to the incredible work from the ladies who made our worst-dressed list, but Anna Chlumsky’s shapeless minidress-and-train combo in 2016 left us scratching our heads, as did the shredded slip dress Portia de Rossi wore in 1999. And that’s just the tip of the disheveled iceberg. But hey, tastes and perspectives change. Céline Dion’s 1999 Oscars look topped the worst-dressed lists but it’s iconic today. Still, we don’t see these Emmys outfits winning over our hearts anytime soon.
Gwyneth Paltrow looked ready to flap her wings and fly away in 2019
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Gwyneth Paltrow has become almost synonymous with quiet luxury and a more toned-down aesthetic, but the look she chose for the 71st annual Emmys in September 2019 was anything but minimal. It was decidedly big, bold, and bizarre. The actor-turned-entrepreneur donned a vintage Valentino Haute Couture column gown that, we fear, should’ve been left in the ’60s. The record-scratch moment came via the sleeves, a comical sea of tulle strips that could’ve come from a community theater’s costume department. It’s a shame because the dress would’ve been simple and chic without the whacky feather wing things.
Anna Chlumsky’s 2016 potato sack dress was just plain bizarre
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Anna Chlumsky’s look at the 68th annual Emmys in September 2016 was a masterclass on what not to do with texture and proportion. The beige-colored frock looked tacked together by a design student. Wonky hem and sloppy draping, anyone? The color completely washed the “My Girl” star out, and the dress’ silhouette made little sense. It’s hard to tell what the plan was, but this fabric — with its hive-like texture — was too stiff and heavy to create any sort of rhythm. We love a dramatic cape moment, but this one was a swing and a messy miss.
Fiona Dourif’s furry frock was eye-catching in all the wrong ways in 2026
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Fiona Dourif and her look made our list as one of the worst-dressed celebs at the 2026 Emmys. Sadly, the Thomas Hanisch oxblood-colored ‘fit didn’t give us the warm and fuzzies. The poncho was the oddest of choices that felt nabbed from the set of a movie where a group of 19th century explorers gets stranded in the cold wilderness. Instead of reading luscious and expensive, the fur-like fabric felt stiff and uncomfortable, like it might be prickly to the touch. But Dourif’s baby bangs were cool, and the type of cute-quirk we wish we saw throughout her look.
Mary Tyler Moore’s 1988 dress was more craft project than fashion
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The icon Mary Tyler Moore attended the 40th Emmys in August 1988 in a less-than-legendary Arnold Scaasi gown that proved why colorblocking should be approached carefully and with the utmost of care. Moore’s dress looked like someone gathered up the tablecloths from a baby shower and haphazardly wrapped the fabrics around her frame — and tied them all together with a giant bow. The garish choker and sash-like shawl didn’t help matters. To be sure, each color is pretty on its own, but all three together created an overdone clash that we wish we could wipe from Moore’s record.
Portia de Rossi’s 1999 slip dress served Spirit Halloween couture
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We could write a dissertation on the iconic ’90s slip dress, and Portia de Rossi’s look from the 51st Emmys in September 1999 would go in the “Don’t Do This” subsection. The “Arrested Development” star was all smiles on the bustling red carpet, but her black dress was anything but joyful. We suppose she was going for gothic glamour, but between the shredded hem and the poor fit, Rossi’s look was less dark romance and more inexpensive Halloween costume. The silver lining situation was as odd as the thigh-high socks, but the gold wire shoulders were fun.
Heidi Klum’s 2015 chick-yellow dress was a confusing hodgepodge
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They say a supermodel can wear anything, but the ‘fit Heidi Klum wore to walk the 67th Emmys red carpet in September 2015 put that adage to the test. The beauty draped her nearly 5-feet-10-inch frame in a canary-yellow Versace dress that was a real-life example of the power of editing in fashion. No doubt, the color — albeit, a bit Big Bird-like — was sweet and ethereal, but perhaps we didn’t need the mesh, and the rhinestones, and the petal appliqués, and the shredded fringe sleeve thing? We wanted more polish from the “Project Runway” OG.
Calista Flockhart’s 2024 ‘fit looked straight out of the ’80s
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The 75th Emmys had to be pushed from September 2023 to January due to a writers’ strike, and maybe the change in dates left Calista Flockhart discombobulated, because her outfit looked ripped from the ’80s, and not in a good way. Flockhart donned an Armani Privé look that featured a turquoise button-up bodice — aplenty with sheer, shine, and ruffles — and a structured circle skirt with neon stripes. We wish we could say the problem was the pairing, but it’s not. Each element flopped, and the entire look lacked the sophistication befitting an old-school Hollywood star.
Sarah Silverman drowned in a messy sea of overworked fabric in 2009
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Comedian Sarah Silverman walked the red carpet at the 61st Emmys in September 2009 in a cobalt-blue gown, and we’re still not totally sure whether it was meant to be satire. Yes, it was that comically bad. She had been working with Badgley Mischka on the gown, but horrified by Silverman’s requested alterations including the added hip panels, the designers insisted she not use the brand’s name, according to the New York Times. Oof. She said she wanted to look regal. Princess? Not quite. Palace curtains? You bet. The jewel-toned blue looks gorgeous against her skin, though.
Zosia Mamet’s psychedelic gown was anything but groovy in 2013
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It’s exciting when a celeb opts for a print on the red carpet: high risk, high reward. Zosia Mamet’s dicey move at the 65th Emmys in September 2013 was a funkadelic fail, unfortunately. The Honor Resort dress’ splotchy print reminds us of the tie-dye shirt you made at camp as a kid to only end up ever sleeping in. And if the pattern was meant to be artsy and cerebral, the whole thing was undone by the addition of the leather bustier that looks stuck on with velcro and the bib-like neck, both of which feel sort of silly.
Barbra Streisand missed the mark on the peasant look in 2004
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Barbra Streisand is our forever funny girl, and the look she wore to the 56th Emmys in September 2004 certainly garnered some chuckles — and a few seriously confused faces. The legendary star went the monochromatic route with the help of all-over blush pink, which was a tough start. Streisand’s ‘fit featured a floor-length satiny gown, the dropped shoulders trimmed in tiny roses that would’ve been more at home on a wedding cake, and a real-life velvet cape. The whole look was part-nightie, part-peasant, and totally strange.
