Revisiting the 10 Best Red Carpet Fashion Looks of 2019

4:41 PM 12/20/2019

by Ingrid Schmidt

From Billy Porter's gender-bending look at the Oscars to Lady Gaga's head-to-toe blue ensemble at the Golden Globes to J. Lo's Grammys dress redux in Milan, here are the fashion highlights of the year.

From left: Lady Gaga, Billy Porter, Jennifer Lopez
From left: Lady Gaga, Billy Porter, Jennifer Lopez
George Pimentel/WireImage; Frazer Harrison/Getty Images; Miguel Medina/AFP via Getty Images

Billy Porter wins the year in style by championing gender fluidity — most memorably by stepping out in February in a black velvet tuxedo gown and bolero jacket, designed by inclusive fashion designer Christian Siriano, at the 91st Academy Awards.

One-upping herself, Jennifer Lopez created a jaw-dropping moment that shut down Milan Fashion Week when she sauntered down the runway at the spring 2020 Versace show in a new, even more revealing riff on that jungle-print Grammys dress from 20 years ago — looking better than ever.

Of Lady Gaga’s many standout looks in 2019, her periwinkle blue Valentino haute couture gown (with hair dyed to match), finished off with $5 million worth of Tiffany & Co. diamond jewelry for the Golden Globes took top prize.

Also on the list — highlights of 2019 as it was next-to-impossible to narrow all the year’s amazing ensembles to just 10 — are Gemma Chan at the Oscars (fuschia Valentino couture with pockets), Beyonce at the Lion King premiere in the U.K. (in a golden goddess gown with a slit up to there), Zendaya at the Emmys (channeling Poison Ivy), Chadwick Boseman at the SAG Awards (rocking $35,000 worth of brooches) and Elle Fanning at the Cannes Film Festival (Old Hollywood glam in new “New Look” Dior).

Keep reading to see all of the year's top looks.

  • Billy Porter

    Oscars 2019

    The Emmy-winning, boundary-pushing Pose star wowed at every red carpet opportunity, blazing the way for non-binary fashion with a series of winning gender-fluid looks. At the Oscars in 2019, he stepped out in a gender-bending, tuxedo-inspired black velvet bolero jacket and ballgown custom-made by New York-based fashion designer Christian Siriano, known for his inclusive designs. Just ahead of the Emmys, Porter (styled by Sam Ratelle) told THR, "My goal was to start a conversation where gender has no place in fashion."

  • Jennifer Lopez

    J. Lo shut down Milan Fashion Week at the Versace spring 2020 show in that jungle-print dress that she made forever-iconic on the red carpet at the Grammys in 2000 — and reportedly led to the creation of Google Image Search. The fashion redux included a new riff on the frock that was even more barely-there than the original design with the ever-plunging neckline. And the 50-year-old singer-actor rocked the runway, looking better than ever. (Since it technically originated on a red carpet, this look was voted in.)

  • Lady Gaga

    The Star Is Born actress stunned at the 76th annual Golden Globes in head-to-toe blue (literally) — from a cerulean blue hairdo (inspired by 16th century European aristocracy) to a matching Valentino haute couture gown with off-the-shoulder puff sleeves and a dramatic train. The style resembled a pale blue dress that Judy Garland wore in the original 1954 film. Styled by Tom Eerebout and Sandra Amador, Gaga accessorized with $5 million worth of Tiffany & Co. diamonds for added dazzle.

  • Gemma Chan

    Setting a standard for the evening’s hottest hue (pink), the Crazy Rich Asians star took home the prize as No. 1 on the THR best-dressed list at the 91st annual Academy Awards in a voluminous, ruffled taffeta Valentino haute couture gown complete with practical pockets. Chan’s stylist Rebecca Corbin-Murray told THR: "The color is so joyful and the silhouette is glorious. It’s everything modern haute couture should be. We had the Jimmy Choo bag and shoes hand-dyed to match."

  • Zendaya

    Stepping out to present an award at the Emmys with newly auburn locks coiffed into soft waves, the Euphoria actress (styled by Law Roach) looked ravishing in a custom, corseted green silk charmeuse gown by Vera Wang with an asymmetric va-va-voom slit. She accessorized the dress (inspired by DC Comics character Poison Ivy) with custom-dyed satin pumps by Brian Atwood.

  • Beyoncé

    While mingling with Duchess of Sussex Meghan Markle and Prince Harry, Bey royally slayed in the fashion department, donning a golden-toned goddess gown with a slit up to there and a regal train at the Lion King premiere in London in July. She paired the custom Cong Tri gown with gilded Jimmy Choo sandals, Lorraine Schwartz jewelry and a round gold clutch handbag by Anna Cecere.

  • Chadwick Boseman

    The Black Panther star crushed it all season, particularly at the SAG Awards in a custom, one-of-a-kind Ermenegildo Zegna XXX look: a leaf-print, shawl-collar dinner jacket worn over a brown turtleneck and black tux pants. Styled by Ashley Weston, Boseman deftly accessorized with three statement-making Tiffany & Co. diamond brooches on his lapel (worth over $35,000) and mixed-media patent, velvet and suede Christian Louboutin dress shoes.

  • Elle Fanning

    Jury member Elle Fanning turned up in a series of fantastic fashion moments during the Cannes Film Festival in May, thanks to longtime stylist Samantha McMillen. Her standout new "New Look" at the Once Upon a Time in Hollywood premiere (inspired by a 1947 photograph) channeled Old Hollywood glamour and took over 450 hours to create. The Dior haute couture ensemble consisted of an ivory silk organza pussybow blouse with drapey sleeves, a pleated blue tulle A-line skirt and a wide-brimmed black macramé hat — très chic!

  • Timothee Chalamet

    Demonstrating how he commands the red carpet, Chalamet once again broke all the fashion rules (and looked good doing it) at the Venice Film Festival premiere of The King. The 23-year-old styled himself in a silvery-gray, single-breasted satin suit with a double-banded waist sash by his favorite designer, Haider Ackermann. His devil-may-care attitude was revealed in the pant cuffs, imprecisely rolled to reveal easygoing black boots. Because he can.

  • Mahershala Ali

    Nabbing a best supporting actor Oscar for his role in Green Book, Ali fit the part in an elegant ensemble he pulled together with longtime stylist Van Van Alonso. His black brocade jacket with a matching vest, Mandarin-collar white dress shirt and black tuxedo trousers were custom-created by Ermenegildo Zegna XXX. Ali accessorized with Christian Louboutin patent-velvet-suede dress shoes, a Cartier watch, custom Cutler and Gross eyeglasses and a black custom-made Gigi Burris hat inspired by a Jinnah cap.