The 100 Most Memorable Fashion Moments of 2019

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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.

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1. Red Carpet Winner: Gemma Chan

MARK RALSTON/Getty Images

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.

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2. Red Carpet Winner: Brie Larson

Brie Larson at the Avengers: Endgame premiere

VALERIE MACON/Getty Images

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.

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3. Red Carpet Winner: Elle Fanning

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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.

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4. Red Carpet Winner: Zendaya

NINA PROMMER/EPA-EFE/Shutterstock

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.

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5. Red Carpet Winner: Cate Blanchett

Cate Blanchett at the 2019 Zurich Film Festival

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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.

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6. Red Carpet Winner: Laura Harrier

Jordan Strauss/Invision/AP/Shutterstock

Harrier brought sustainable style to the Oscars with this Nicolas Ghesquière-designed Louis Vuitton creation, which was made entirely of eco-friendly materials.

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7. Red Carpet Winner: Zoë Kravitz

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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?"

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8. Red Carpet Winner: Gwendoline Christie

Gwendoline Christie 2019 Game of Thrones premiere

ANGELA WEISS/Getty Images

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.

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9. Red Carpet Winner: Janelle Monáe

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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.

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10. Red Carpet Winner: Charlize Theron

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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.

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11. Red Carpet Winner: Billy Porter

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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.”

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12. Red Carpet Winner: Dame Helen Mirren

Helen Mirren Catherine the Great premiere

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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.

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13. Red Carpet Winners: Zendaya and Michael B. Jordan

Zendaya and Michael B. Jordan in the same suit

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Turns out, these two have the same taste in menswear. So who wore this Berluti suit better? “Zendaya. Hands down, no contest,” said Jordan.

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14. Red Carpet Winner: Selma Blair

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“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.

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15. Red Carpet Winner: Melissa McCarthy

Dia Dipasupil/Getty Images

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.

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16. Acquired Tastes: Scrunchies

Dakota Johnson and Jason Momoa scrunchies

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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.

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17. Acquired Tastes: Footwear Gone Mad

Getty Images, Courtesy Margiela, Courtesy Puppets and Puppets

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.”

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18. Acquired Tastes: Bowl Cuts

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Mushrooms, not the kind favored by Harry Styles, are sprouting up everywhere, including the bowls served by Sam McKnight for Fendi Couture.

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19. Acquired Tastes: Baby Bags

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Teeny, tiny accessories sure are cute, but where do these people keep their wallets and lipstick? Barbie has a bigger bag…

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20. Acquired Tastes: Hats Off

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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.

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21. Acquired Tastes: Puff Piece

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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.

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22. Acquired Tastes: Taking a Bow

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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.

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23. Celebs on the Runway: Jennifer Lopez at Versace

PIXELFORMULA/SIPA/Shutterstock

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.

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24. Celebs on the Runway: Chloë Sevigny at Simone Rocha.

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Everyone in favor of Sevigny playing a royal — and using this look as her audition — say "I."

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25: Celebs on the Runway: Helen Mirren at L’Oréal Paris.

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Mirren could have easily walked off the runway and onto the red carpet in this dress.

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26. Celebs on the Runway: Penélope Cruz in Chanel

Victor VIRGILE/Getty Images

If only this look was actually acceptable to ski in, we'd be on the slopes all the time.

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27. Celebs on the Runway: Grace Jones at Tommy x Zendaya

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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.

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28. Celebs on the Runway: Tilda Swinton at Undercover

Courtesy Undercover

OK, so Swinton wasn’t actually modeling the dress, but she did appear as a print in this Suspiria-inspired collection.

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29. The Queen: Olivia Colman

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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.

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30. Horsin' Around: Lil Nas X and Justin Bieber

Courtesy

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.

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31. Not So Cynical: Billie Eilish

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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.

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32. Keeping Up With the Jonases

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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).

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33., 34., & 35. Ones to Watch

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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.

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36: Lashing Out: Valentino Couture

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During Fashion Week, all eyes were on the fantastical hand-cut and hand-dyed feather lashes dreamed up by makeup master Pat McGrath.

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37. Good as Hell: Lizzo

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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!

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38. A Year in J.Lo

Evan Agostini/Invision/AP/Shutterstock

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.

SEPT.: Hustlers
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.

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39. Badass Women of the Year: Greta Thunberg

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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.

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40. Badass Women of the Year: The U.S. Women's Soccer Team

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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.

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41. Badass Women of the Year: Ali Stroker

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“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.

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42: Badass Women of the Year: The New Charlie's Angels

NADJA KLIER/Columbia Pictures

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.

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43. Badass Women of the Year: Jodi Kantor and Megan Twohey

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In their book, She Said, the Pulitzer Prize-winning reporters recount their New York Times exposé of Harvey Weinstein and how it helped reignite the #MeToo movement.

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44. Badass Women of the Year: Marsai Martin

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At 14, Martin has lived up to the title “girlboss,” becoming the youngest executive producer of a major Hollywood film for her comedy, Little.

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45. Badass Women of the Year: Phoebe Waller-Bridge

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“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.

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46. Badass Women of the Year: Coco Gauff and Naomi Osaka

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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.

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47. Badass Women of the Year: Gayle King

CBS

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.

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48. Badass Women of the Year: Simone Biles

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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.

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49. Badass Women of the Year: Michelle Williams

Kevin Winter/Getty Images

“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.

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50. Equal Playing Field

Mattel

In September, Mattel released Creatable World, a line of gender-neutral dolls designed to “keep the labels out and invite everyone in.”

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51. Page-Turner

Nan A. Talese / Doubleday

Margaret Atwood answered all our burning questions about Gilead in The Testaments, her sequel to The Handmaid’s Tale.

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52. Beyoncé Goes Documentarian

Netflix

Queen B lifted the curtain with two docs: Homecoming and Beyoncé Presents: Making the Gift, about Beychella and her latest album, respectively.

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53. Big-Coat Energy

Andrew Harnik/AP/Shutterstock

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.

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54. Year in Style: Hit Parade

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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).

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55. Year in Style: Wingless Victory

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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.

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56. Year in Style: Return to Sender

Victor VIRGILE/Getty Images

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.

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57. Year in Style: Meghan Goes BOGO

WPA Pool/Getty Images

That’s buy one, give one free. The Duchess of Sussex created a capsule collection (including the Misha Nonoo–designed blouse below) that benefits the British charity Smart Works. For every piece purchased, one will be donated to an unemployed woman going on job interviews.

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58. Year in Style: That's Entertainment

Nicholas Hunt/Getty Images

Barry Manilow performed “Copacabana” at the finale of a Michael Kors show.

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59. Year in Style: That's Entertainment

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Ralph Lauren surprised his audience with a nightclub set featuring a glass-shattering rendition of “Fly Me to the Moon” by Janelle Monáe. It used to be enough for a designer to just show some clothes.

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60. Year in Style: Mister Fashion

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Taking over as chairman of the CFDA, Tom Ford shook things up with a dramatically shorter New York Fashion Week and a more diverse board of directors. He’s got our vote.

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61. Year in Style: LV's Zip Drive

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For his N.Y.C.-inspired cruise collection, Nicolas Ghesquière created handbags with video displays that rival the billboards in Times Square. The flexible LED screens easily captured the title of this year’s IT bag.

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62. Year in Style: Next Generation

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Fashion’s eternal obsession with youth has sparked a hiring trend of millennial designers including Daniel Roseberry at Schiaparelli, Bruno Sialelli at Lanvin, Daniel Lee at Bottega Veneta and Rushemy Botter & Lisi Herrebrugh at Nina Ricci.

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63. Year in Style: MVP of 2019

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Brandon Maxwell had quite a year, from orchestrating Lady Gaga’s 16-minute, four-outfit grand entrance at the Met Gala to winning the big-league Womenswear Designer of the Year award from the CFDA.

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64. Year in Style: Farewell to Karl

Vittorio Zunino Celotto/Getty Images

Fashion lost its ultimate icon with the passing of Karl Lagerfeld, who created collections for Chanel, Fendi, and his namesake label for so many decades that he was considered the world’s most prolific designer. Beyond his boundless imagination, he was known for his wicked quips (“sweatpants are a sign of defeat”) and his extravagant runway shows, one of which even included the simulated blastoff of a rocket ship.

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65. Year in Style: End of the Road

Courtesy Calvin Klein

After dropping Raf Simons in 2018, Calvin Klein, one of the last great American mega-brands, announced it was getting out of the luxury market for now, focusing instead on its more lucrative fragrances and jeans.

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66. Year in Style: He'll Be There For You

Courtesy Ralph Lauren

To fête the 25th anniversary of Friends, Ralph Lauren launched a Central Perk-worthy collection, ostensibly to remind everyone that he once made a cameo on the show as Rachel’s boss.

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67. Year in Style: Just Dropping In

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Satoshi Kondo got off to an unforgettable start as design director of Issey Miyake with dresses that floated down from the rafters and landed on the underwear-clad models standing beneath them.

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68., 69., & 70. The New Beauty Moguls

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“The last thing the world needs is another beauty brand, but that’s too bad,” Lady Gaga said in the understatement of the year, given the number of celebrities promoting new products: Gaga débuted Haus Laboratories makeup for Little Monsters, Chloë Sevigny launched a fragrance for cool girls, Millie Bobby Brown started Florence by Mills for Gen Z, and Tracee Ellis Ross created Pattern hair products for the “curl community.”

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71. Sexy Seth

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In a move that no one saw coming, Seth Rogen had the style glow-up of the year, trading in his casual duds for pink suits and Prada.

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72. Lots in Space: Light Year

Courtesy Event Horizon Telescope Collaboration

The 50th anniversary of the moon landing sparked an intergalactic trend that did not go unnoticed by fashion, film, or anybody looking up. Astronomers even revealed the first picture of a black hole or, as the memes later theorized, a blurry plain toasted bagel.

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73. Lots in Space: Starstruck

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Tessa Thompson went sci-fi chic with custom Rodarte and a Judith Leiber moon bag.

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74. Lots in Space: Starstruck

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Gugu Mbatha-Raw’s Gucci dress with crystal moon-and-star embroidery made for a high-couture constellation.

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75. Lots in Space: Closet Encounters

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Earth to Rick Owens: Take me to your leader.

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76. Lots in Space: Out of the Blue

JASON SZENES/EPA-EFE/Shutterstock

Gypsy Sport designer Rio Uribe’s typically diverse casting now also welcomes aliens.

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77. Lots in Space: Moon Shot

Everett Collection

The documentary Apollo 11 invited viewers onboard.

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78. Lots in Space: Rocket Man

Francois Duhamel/Twentieth Century Fox

Brad Pitt brought deep thoughts to deep space in Ad Astra.

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79. Lots in Space: Ladies Who Launch

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After the first all-female space walk was delayed because NASA didn’t have space suits in the right sizes, astronauts Jessica Meir and Christina Koch made history in October when they ventured outside the International Space Station for more than seven hours.

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80. Lots in Space: Space Jammies

Virgin Galactic

Virgin Galactic unveiled space suits for tourists designed by Under Armour, free with purchase of a $250,000 ticket.

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81. Lots in Space: Galaxy Gal

Alfredo Flores

82. GALAXY GAL: As Shangela says on Ariana Grande’s “NASA” single, “One small step for woman, one giant leap for womankind.”

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82 - 86. Send in the Clowns

Fredrik Tjærandsen, Getty Images

In the circus of fashion, voluminously zany dresses are all the rage, none more delightful than the tulle confections of the Japanese design star Tomo Koizumi. Jeremy Scott’s Picasso tribute show for Moschino cast Bella Hadid in the role of the harlequin, while Christopher Kane riffed on balloons as a print and Central Saint Martins grad student Fredrik Tjærandsen inflated them into marvelous dresses on the runway. Everybody loves a clown, unless it’s the Joker (for obvious reasons) or Sean Spicer on Dancing with the Stars (because that’s just sad).

Pictured: Fredrik Tjærandsen, Christopher Kane, Moschino.

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87. All Tim, All the Time

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When he’s not making news with his luscious locks, Timothée Chalamet serves as America’s next top model for menswear. These sweet looks are by Haider Ackermann, Alexander McQueen, and S.R. Studio. LA. CA.

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88. Chips off the Old Catwalk: Damien Hurley

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The son of Elizabeth, Hurley invited familial comparisons by emulating some of her famous moments lately, although his Versace safety-pin suit was more darling than daring.

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89. Chips off the Old Catwalk: James Turlington

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Turlington announced this summer that he was giving up his day job as a pro baseball player to follow in the footsteps of Aunt Christy, landing a look in Brandon Maxwell’s collection that she might approve of.

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90. Chips off the Old Catwalk: Kaia Gerber

Splash News, Getty Images

Cindy Crawford told us the black lace Versace bondage dress she wore to the 1992 MTV Video Music Awards remains one of her all-time favorites. Her daughter then paid homage to the model on her 18th birthday.

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91. Swift Moves

Kevin Mazur/Getty Images

With a new album and a new outlook on life, Taylor Swift made amends with old foes (ahem, Katy Perry), took on the injustices of the music world and the LGBTQ+ community, and reminded everyone that they need to calm down.

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92. Golden Hour

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Country crossover Kacey Musgraves swept the Grammys, picking up every trophy she was nominated for, including the coveted Album of the Year.

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93. Staying in Character: Margot Robbie

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For the press tour of Once Upon a Time in Hollywood, Robbie channeled the breezy 1960s style of Sharon Tate.

Pictured: Oscar de la Renta, Jacquemus, Dries Van Noten.

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94. Going Viral

Germano Poli / EyeEm/Getty Images

It took a simple picture of an egg to unseat Kylie Jenner as the most-liked picture on Instagram.

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95. Flappuccino

HBO

The only thing more embarrassing than the coffee cup in Game of Thrones would be a barista trying to spell “Daenerys.”

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96. All Wet

Stefanie Keenan/Getty Images

Was the Fiji Water Girl a clever publicity stunt or simply the world’s best photobomber? More important, did anyone actually take any water?

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97. Age Is But a Filter

Courtesy The Jonas Brothers

FaceApp’s aging tool made it possible to imagine what we might look like when we get old — or abandon our skincare routines.

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98. Quote of the Year

HBO/Kobal/Shutterstock

“I will not not be rich.” Laura Dern as Renata Klein on HBO’s Big Little Lies season 2

was the definition of a mood.

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99. Family Ties

Pool/Getty Images

Born on May 6, Archie Harrison Mountbatten-Windsor has already inherited his dad’s fiery red hair and his mom’s flair for affordable fashion (these overalls are by H&M Conscious).

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100: Knit Pick: Katie Holmes's Sweater

The Mega Agency

After a shot of the star hailing a cab made the Instagram rounds, Holmes' Khaite cashmere bra and sweater sold out in hours. “I wasn’t anticipating that it would be so sought-after,” she says. “But, it is a pretty great sweater.”

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The 100 Most Memorable Fashion Moments of 2019

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1. Red Carpet Winner: Gemma Chan

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2. Red Carpet Winner: Brie Larson

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3. Red Carpet Winner: Elle Fanning

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4. Red Carpet Winner: Zendaya

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5. Red Carpet Winner: Cate Blanchett

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6. Red Carpet Winner: Laura Harrier

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7. Red Carpet Winner: Zoë Kravitz

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8. Red Carpet Winner: Gwendoline Christie

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9. Red Carpet Winner: Janelle Monáe

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10. Red Carpet Winner: Charlize Theron

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11. Red Carpet Winner: Billy Porter

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12. Red Carpet Winner: Dame Helen Mirren

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13. Red Carpet Winners: Zendaya and Michael B. Jordan

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14. Red Carpet Winner: Selma Blair

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15. Red Carpet Winner: Melissa McCarthy

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16. Acquired Tastes: Scrunchies

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17. Acquired Tastes: Footwear Gone Mad

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18. Acquired Tastes: Bowl Cuts

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19. Acquired Tastes: Baby Bags

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20. Acquired Tastes: Hats Off

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21. Acquired Tastes: Puff Piece

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22. Acquired Tastes: Taking a Bow

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23. Celebs on the Runway: Jennifer Lopez at Versace

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24. Celebs on the Runway: Chloë Sevigny at Simone Rocha.

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25: Celebs on the Runway: Helen Mirren at L’Oréal Paris.

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26. Celebs on the Runway: Penélope Cruz in Chanel