The 100 Most Memorable Fashion Moments of 2019
Who knew a single year could feel like a whole decade? That’s how, um, eventful 2019 was. Still, this past round 365 wasn’t all gloom and doom. There were plenty of positives that are worth looking back on — especially if we're talking in terms of fashion and badass women.
Red carpet outfits were over-the-top. The runway introduced us some pretty bold choices and styling tricks. We fell in love with a whole new crop of style icons. Heck, we even considered getting a bowl cut (at least for a minute).
In case you need a refresher or a quick pick-me-up before 2020 comes rolling in at full force, we’ve rounded up 100 of the best style moments of the year, ahead.
1. Red Carpet Winner: Gemma Chan
Chan hit a fashion peak at the Oscars in this voluminous Valentino Haute Couture number, complete with a ruffled collar, a sweeping train, and pockets that she revealed were stuffed with chocolate chip cookies.
2. Red Carpet Winner: Brie Larson
We marveled at Larson’s parade of downright heroic looks this year, which featured everything from couture capes to custom jewelry. Plus, the actress wasn't afraid to show a little leg in a purple Celine by Hedi Slimane dress, which she wore to the premiere of Avengers: Endgame.
3. Red Carpet Winner: Elle Fanning
It took 450 hours for Maria Grazia Chiuri’s team at Dior to perfect this modern take on the fashion house’s iconic New Look — and the payoff was très chic. “It’s my favorite thing I’ve ever worn,” says Fanning.
4. Red Carpet Winner: Zendaya
Zendaya’s jaw-dropping Emmys look reminded her fans of Batman’s nemesis Poison Ivy, but stylist Law Roach said the Vera Wang Collection dress was referencing the Emerald City scene in The Wiz.
5. Red Carpet Winner: Cate Blanchett
To accept the Golden Icon Award at the Zurich Film Festival, Blanchett dressed the part in a Gaultier Paris gown that was dripping with gilded embellishment.
6. Red Carpet Winner: Laura Harrier
Harrier brought sustainable style to the Oscars with this Nicolas Ghesquière-designed Louis Vuitton creation, which was made entirely of eco-friendly materials.
7. Red Carpet Winner: Zoë Kravitz
Only Kravitz could pull off a $24,000 Tiffany & Co. bra made of 18-karat gold with an ease that says, “Oh, this old thing?"
8. Red Carpet Winner: Gwendoline Christie
After surviving years of shocking plot twists, Christie somehow managed to find an Iris van Herpen dress for the final Game of Thrones première that had as much high drama as the beloved series.
9. Red Carpet Winner: Janelle Monáe
We tip our hat to Monáe’s Christian Siriano Met Gala look, which boasted stacked millinery and a mechanical eye programmed to wink at random.
10. Red Carpet Winner: Charlize Theron
Who’s that girl? The morning of the Oscars, Theron decided to chop off her hair, débuting a sleek brunet bob that perfectly framed her cornflower blue, Dior Haute Couture turtleneck gown.
11. Red Carpet Winner: Billy Porter
The Pose star defied fashion norms at the Oscars, arriving in a custom Christian Siriano tuxedo-jacket-and-gown combo that he hoped would “create a conversation around what gender means.”
12. Red Carpet Winner: Dame Helen Mirren
In a move that rivaled Lady Gaga’s egg entrance, Mirren raised the bar by arriving at the première of Catherine the Great in a sedan chair.
13. Red Carpet Winners: Zendaya and Michael B. Jordan
Turns out, these two have the same taste in menswear. So who wore this Berluti suit better? “Zendaya. Hands down, no contest,” said Jordan.
14. Red Carpet Winner: Selma Blair
“There are moments that define us, and this is one of those,” said Blair (in Ralph & Russo Couture) at the Vanity Fair Oscar party, where she made her first public appearance after announcing her MS diagnosis.
15. Red Carpet Winner: Melissa McCarthy
For the Oscar after-parties, McCarthy showed up in— gasp!—something you can actually dance in. Husband Ben Falcone also donned a tracksuit in solidarity.
16. Acquired Tastes: Scrunchies
It seems obvious that scrunchies could double as bracelets, but it took Dakota Johnson (with a Sophie Buhai scrunchie) and Jason Momoa (with a Fendi scrunchie) to make them worthy of the red carpet.
17. Acquired Tastes: Footwear Gone Mad
Designers are making shoes out of anything these days, including Flipper, a rose-and-cigarette combo, and a foam carton that gives new meaning to the phrase “walking on eggshells.”
18. Acquired Tastes: Bowl Cuts
Mushrooms, not the kind favored by Harry Styles, are sprouting up everywhere, including the bowls served by Sam McKnight for Fendi Couture.
19. Acquired Tastes: Baby Bags
Teeny, tiny accessories sure are cute, but where do these people keep their wallets and lipstick? Barbie has a bigger bag…
20. Acquired Tastes: Hats Off
Hats are getting bigger, though it’s not entirely clear whether these are meant for those seeking more privacy or more attention. Pictured: Tom Brady in Nick Fouquet, Jennifer Lopez in Sally LaPointe, and Billy Porter in Stephen Jones.
21. Acquired Tastes: Puff Piece
Bigger was certainly better this year, as stars opted for larger-than-life layers of tulle and swaths of chiffon in shades that were decidedly sweet. Tracee Ellis Ross wowed in Marc Jacobs, Kacey Musgraves looked sweet Giambattista Valli Haute Couture, Priyanka Chopra Jonas went bridal in Georges Hobeika.
22. Acquired Tastes: Taking a Bow
Whether worn off the shoulder or on top of the head, the bow trend was knot to be missed. Pictured: Elle Fanning in Kimhēkim, Zendaya in Alexis Mabille, Lucy Boynton in Patou.
23. Celebs on the Runway: Jennifer Lopez at Versace
It used to be big news when A-listers sat front row at a fashion show. Now, you’re nobody unless there’s a superstar on your runway.
24. Celebs on the Runway: Chloë Sevigny at Simone Rocha.
Everyone in favor of Sevigny playing a royal — and using this look as her audition — say "I."
25: Celebs on the Runway: Helen Mirren at L’Oréal Paris.
Mirren could have easily walked off the runway and onto the red carpet in this dress.
26. Celebs on the Runway: Penélope Cruz in Chanel
If only this look was actually acceptable to ski in, we'd be on the slopes all the time.
27. Celebs on the Runway: Grace Jones at Tommy x Zendaya
Is there a world record for the amount of icons in one show? Because Tommy x Zendaya seem to be competing for the winning title.
28. Celebs on the Runway: Tilda Swinton at Undercover
OK, so Swinton wasn’t actually modeling the dress, but she did appear as a print in this Suspiria-inspired collection.
29. The Queen: Olivia Colman
Colman had a royally good 2019. After celebrating a best actress Oscar win for her portrayal of Queen Anne in The Favourite, she took on the role of Queen Elizabeth II in The Crown. Bow down, people.
30. Horsin' Around: Lil Nas X and Justin Bieber
Ever since Lil Nas X’s inescapable “Old Town Road” became the longest-running No. 1 single in Billboard’s history, everybody’s been getting a little bit country. Even Bieber released a twangy single with Dan + Shay called “10,000 Hours,” which is about how long it’s been on repeat.
31. Not So Cynical: Billie Eilish
The 17-year-old shut down the shamers this year by revealing that the reason she wears baggy clothes is to keep her body a mystery. “Nobody can have an opinion because they haven’t seen what’s underneath,” she said, ironically in an ad for Calvin Klein.
32. Keeping Up With the Jonases
A new album, a documentary, and a whole lot of weddings made the Jonas Brothers (and newly appointed J Sisters) the family to follow.
Joe Jonas and Sophie Turner: In between Jo Bros concerts and Game of Thrones-finale madness, the lovebirds found time to pull off not one but two secret weddings this year.
Nick Jonas and Priyanka Chopra Jonas: After their 2018 nuptials, the duo swiftly settled into wedded bliss and his-and-her red-carpet looks. As for tour life? Chopra Jonas admits she’s a “full groupie now.”
Kevin Jonas and Danielle Jonas: The couple celebrate their 10th anniversary this month, showing the others how to keep a good thing going, all while balancing kids and careers (Danielle is a jewelry designer).
33., 34., & 35. Ones to Watch
These three up-and-comers (Maya Hawke in Olivier Theyskens, Margaret Qualley in Gucci, and Joey King in Zac Posen) made their mark with a mix of can’t-miss performances, awards-season buzz, and, yes, fashion savvy well beyond their years.
36: Lashing Out: Valentino Couture
During Fashion Week, all eyes were on the fantastical hand-cut and hand-dyed feather lashes dreamed up by makeup master Pat McGrath.
37. Good as Hell: Lizzo
First, her self-love single “Truth Hurts” broke Billboard records. Then, Lizzo's scene-stealing turn in Hustlers helped the film gross over $100 million domestically. She’s even boosted flute sales by giving her beloved Sasha Flute top billing. Band geeks, rejoice!
38. A Year in J.Lo
2019 was proof that it’s Jennifer Lopez’s world and we’re just living in it.
MARCH: Engagement to A-Rod
After two years of dating, Alex Rodriguez popped the question during a getaway in the Bahamas.
JUNE: CFDA Awards
She picked up the Fashion Icon award in a bold look by Ralph Lauren, who, like Lopez, grew up in the Bronx.
JUNE: It’s My Party Tour
To kick off her 50th birthday, Lopez set out on her first concert tour since 2012.
JULY: 50th-Birthday Bash
On the big day she threw the party of the year at Gloria Estefan’s estate in Miami.
Her role as a stripper turned criminal mastermind earned her critical acclaim and early Oscar buzz.
SEPT.: Versace Show
She broke the Internet closing Versace’s spring show in an updated version of her famed Grammys dress.
SEPT.: Super Bowl Announcement
Lopez has no plans to slow down in 2020, already gearing up to headline the Super Bowl halftime show with Shakira.
39. Badass Women of the Year: Greta Thunberg
Whether it’s with her Fridays for Future strikes, her carbon-free transatlantic trip, or her impassioned speech at the United Nations, the 16-year-old activist reminds us what’s really at stake with the climate crisis.
40. Badass Women of the Year: The U.S. Women's Soccer Team
As if a World Cup win weren’t enough, the soccer stars have also become champions off the field in their fight for equal pay.
41. Badass Women of the Year: Ali Stroker
“This award is for every kid watching tonight who has a disability and who has been waiting to see themselves represented,” said Stroker, making history as the first performer in a wheelchair to win a Tony.
42: Badass Women of the Year: The New Charlie's Angels
With a diverse cast and a whip-smart female director (Elizabeth Banks), Ella Balinska, Kristen Stewart, and Naomi Scott were solving crimes and kicking ass in this modern reboot.
43. Badass Women of the Year: Jodi Kantor and Megan Twohey
In their book, She Said, the Pulitzer Prize-winning reporters recount their New York Timesexposé of Harvey Weinstein and how it helped reignite the #MeToo movement.
44. Badass Women of the Year: Marsai Martin
At 14, Martin has lived up to the title “girlboss,” becoming the youngest executive producer of a major Hollywood film for her comedy, Little.
45. Badass Women of the Year: Phoebe Waller-Bridge
“It’s really wonderful to know that a a dirty, pervy, angry, messed-up woman can make it to the Emmys,” said the celebrated Fleabag creator, who took home three statues, including for Lead Actress in a Comedy.
46. Badass Women of the Year: Coco Gauff and Naomi Osaka
The tennis pros taught us all a lesson in sportsmanship when Osaka stopped to console and encourage Gauff after defeating her at the U.S. Open.
47. Badass Women of the Year: Gayle King
Not even an erratic R. Kelly could rattle the CBS This Morning host, who stayed perfectly composed while interviewing the singer, who’s been accused of sexual abuse.
48. Badass Women of the Year: Simone Biles
Is there any record she can’t break? This year Biles became the most decorated gymnast in World Championship history and got the tricky triple-double move renamed in her honor.
49. Badass Women of the Year: Michelle Williams
“The next time a woman, especially a woman of color [...] tells you what she needs in order to do her job, listen to her,” said Williams, turning her Emmy speech into a rousing call to action for widespread pay equity.
50. Equal Playing Field
In September, Mattel released Creatable World, a line of gender-neutral dolls designed to “keep the labels out and invite everyone in.”
Margaret Atwood answered all our burning questions about Gilead in The Testaments, her sequel to The Handmaid’s Tale.
52. Beyoncé Goes Documentarian
Queen B lifted the curtain with two docs: Homecoming and Beyoncé Presents: Making the Gift, about Beychella and her latest album, respectively.
53. Big-Coat Energy
After a heated meeting in the White House, Nancy Pelosi emerged looking cool, calm, and incredibly chic in a Max Mara coat that the brand quickly put back into production.
54. Year in Style: Hit Parade
With two tour de force collections, Marc Jacobs reminded New Yorkers he’s still the biggest show in town even after settling down (he married Char Defrancesco in April and then promptly moved to the suburbs).
55. Year in Style: Wingless Victory
It took Rihanna a single night to obliterate that one-note notion of what it means to be sexy. Her Savage x Fenty lingerie show starring a diverse cast of beauties had viewers poring over Amazon Prime while the Victoria’s Secret Angels had their wings clipped and were taken off the air.
56. Year in Style: Return to Sender
Master disrupter Demna Gvasalia, the designer who made it chic to wear DHL-logo T-shirts, announced his departure from the experimental streetwear collective Vetements. That should free him up to invent even merrier new hemlines during his day job as artistic director of Balenciaga.