20 best, worst and most bizarre Emmys red carpet looks of all time — Angelina Jolie, Sofia Vergara, Jennifer Aniston and more

The 2025 Emmys are just around the corner. After a stellar year of television, some of the biggest names in Hollywood will gather for the 77th Primetime Emmy Awards hosted by comedian Nate Bargatze on Sun. Sept. 14 at 8 p.m. EST at the Peacock Theatre in Los Angeles. This year’s Emmys has some heavy hitters going head-to-head in some tough categories.

Apple TV+’s sci-fi drama Severance leads the pack with 27 nominations, including Outstanding Drama Series and Lead Actor in a Drama Series for actor Adam Scott. Colin Farrell’s The Penguin follows closely behind with 24 nominations, while The White Lotus and Seth Rogan’s series The Studio earned 23 nominations each.

More 2025 Emmy nominations:

• The Last of US (HBO Max) 16 nominations

• Hacks (HBO Max) 14 nominations

• The Bear (FX) 13 nominations

• The Pitt (HBO Max) 13 nominations

Ahead of this year’s awards, we’re looking back at some of the best, worst and most bizarre in Emmys red carpet history.

What did Yahoo Canada readers say last year?

BEST: Jennifer Aniston

Yahoo Canada readers declared Jennifer Aniston’s sequinned column gown by Oscar de la Renta their favourite look from the 2004 Emmys. In a poll of more than 4,000 people, Aniston’s look won 45 per cent of the vote, making The Morning Show actress a winner on the red carpet.

WORST: Maya Rudolph

Rudolph’s bohemian Chloé look didn’t amuse our readers on the 2024 Emmys red carpet. The ruffled mauve gown earned a whopping 69 per cent of reader votes, making it the worst look of the night by far.

BEST: Sarah Jessica Parker

Sex and the City icon Sarah Jessica Parker channelled her inner Carrie Bradshaw when she arrived at the 2000 Emmy Awards in a fashion-forward look by Oscar de la Renta, featuring sequins and feathers.

WORST: Priyanka Chopra

Priyanka Chopra suffered a fashion misstep at the 2017 Emmy Awards in a long-sleeve, feather duster-inspired look by Balmain.

BEST: Drew Barrymore

Barrymore had a princess moment at the 2009 Emmy Awards in a pink ballgown by Monique Lhuillier.

WORST: Aubrey Plaza

Aubrey Plaza turned heads for all the wrong reasons at the 75th Emmy Awards. The White Lotus star wore a satin yellow column gown from Loewe that went viral and had many drawing comparisons to a Post-it note.

BEST: Jennifer Aniston

In 2004, Jennifer Aniston was a red carpet hit in a grecian-inspired gown with gold embellishments by Chanel. The Friends star may not have taken home an Emmy that year for her role as Rachel Green, but she took home the award as best dressed of the night (and perhaps decade).

WORST: Ali Wong

Wong may have won her first Emmy for her role in the miniseries Beef, but we have serious beef with the custom sequinned Louis Vuitton that she chose for the occasion.

BEST: Angelina Jolie

Jolie attended her first Emmys in a nude coloured Randolph Duke gown with sequinned panel. The look was understated elegance, a style she’s become known for throughout her career.

WORST: Lena Dunham

Lena Dunham’s over-the-top Giambattista Valli outfit at the 2014 Emmy Awards was more suited for a girl playing dress-up than an award-winning Girls actress and producer.

BEST: Sandra Oh

Oh, yes! Killing Eve and Grey’s Anatomy alum Sandra Oh proved you don’t have to wear a gown to make the best-dressed list, with a glittering purple Rodarte jumpsuit at the 2022 Emmy Awards.

WORST: Jenny McCarthy

McCarthy’s look at the 2019 Emmy Awards looked as if Cinderella went to the Warped Tour in 2002. While studded belts and combat boots are forever dear to a pop-punk fan’s heart, they should never be seen on the Emmys red carpet.

BEST: Sofia Vergara

Vergara’s curves were on full display in a bold Vera Wang gown at the 2013 Emmy Awards. From the sleek hair to the statement earrings, this red lace gown is still a red carpet favourite to this day.

WORST: Laura Dern

Laura Dern’s talent for choosing roles didn’t spill into her talent for choosing accessories at the 2018 Emmy Awards. The star should’ve leaned into a more minimalist style for her Thom Browne ensemble and left her briefcase purse (and her hot rollers) at home.

BEST: Zendaya

Zendaya’s black satin Valentino ballgown was a showstopper at the 2022 Emmy Awards, as the star picked up her second Emmy for her role in Euphoria that year. She made Emmy history back then, becoming the first Black woman to have two wins in the Outstanding Lead Actress in a drama category, as well as the youngest two-time winner for acting.

WORST: Emma Corrin

Emma Corrin’s Miu Miu bonnet and clawed gloves at the 2021 Emmys were a far cry from her on-screen portrayal as Princess Diana in The Crown. The look was more akin to Freddy Kruger’s baby doll than a buzz-worthy up-and-coming Emmy nominee.

BEST: Sarah Paulson

Paulson shimmered in a sequinned Prada gown at the 2016 Emmy Awards, where she picked up the Emmy for Outstanding Lead Actress in Limited Series or Movie for her role in The People v. O.J. Simpson: American Crime Story.

WORST: Ariel Winter

Modern Family star Ariel Winter’s Steven Khalil look for the 2017 Emmy Awards was a mature choice for the then 19-year-old actress. From the double thigh-high slit to the dark eye-makeup, the sequin-full look was far from her best red carpet ensemble.

BEST: Kerry Washington

Before she was known for her stylish Scandal wardrobe, Kerry Washington set the Emmys red carpet on fire in a sequin Zuhair Murad dress for the 2011 Emmy Awards.

WORST: Heidi Klum

Not even a supermodel could pull off this confusing asymmetrical Versace gown at the 2015 Emmy Awards. Heidi Klum should’ve opted for a look from one of her Project Runway alums, like Cristian Siriano, if she wanted to win the red carpet.

BEST: Angela Bassett

Angela Bassett’s canary yellow Dolce & Gabbana gown with sequinned bodice and asymmetrical-style draping at the 2022 Emmy Awards left the star looking exquisite.

WORST: Quinta Brunson

Quinta Brunson opted for wrinkles and creases at the 75th Emmy Awards. The Abbott Elementary creator and star wore a berry-coloured tea-length Dior gown featuring a belted bow detail.

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