The 10 Most Shocking Fashion Moments of 2019

Fashion: it always shocks and usually pleases.

Whew, 2019 has been a year of delightful surprises and upsetting news—and we’re just talking about what happened in the world of fashion.

It feels like just yesterday that we lost Karl Lagerfeld and bid adieu to Barneys. And we can hardly believe it’s been more than six months since Lady Gaga debuted four outfits in a matter of minutes on the Met Gala red carpet. Here, a look back at the most shocking fashion moments from the past year, in no particular order.

The 10 Most Shocking Fashion Moments of 2019

1. When Jennifer Lopez re-wore that iconic Versace gown

There was hardly an internet to break when Jenny from the Block wore an emerald green, cut-down-to-there, leaf-patterned Versace number to the Grammy Awards in 2000. (But an uptick in queries about the dress did lead to the creation of Google Images.) Anyways, J.Lo surprised showgoers at Milan Fashion Week this year when she took a spin on the runway in a remake of the iconic gown. And—spoiler alert—the sartorial revival was actually created in partnership with Google.

The 10 Most Shocking Fashion Moments of 2019

Dimitrios Kambouris/ Getty Images


Buh-bye, Angels. Last year, the lingerie brand caught plenty of flak when, in an interview with Vogue, they discounted plus-size and trans women. (“We market to who we sell to, and we don’t market to the whole world.” Ouch.) This November, VS said they were canceling the 2019 show entirely in an effort to focus on digital marketing. But we suspect there’s something larger at play. Namely, a recognition that super skinny models prancing around in lingerie no longer feels relevant or, for that matter, aspirational.

The 10 Most Shocking Fashion Moments of 2019


We all want to attend a Chanel runway show, but not quite as much as Marie Benoliel, a 28-year-old professional gate-crasher who actually hoisted herself onto the catwalk so she could strut with the models in the spring/summer 2020 show this past September. But don’t worry, Gigi Hadid took control of the situation by cornering Benoliel and escorting her off the runway. Turns out, the crasher is actually a YouTuber who goes by the moniker Marie S’Infiltre and grew her following by pulling pranks exactly like this. Coco Chanel would not approve.

The 10 Most Shocking Fashion Moments of 2019


It wasn’t just Sex and the City fans who were upset here. The department store’s Madison Avenue flagship was also a beloved stomping ground for devoted New York shoppers looking to buy a Rick Owens puffer coat or new Prada purse. Founded by Barney Pressman in 1923 as a discount men’s clothing store, it grew to become a style mecca that kick-started brands including Proenza Schouler and Alexander Wang, in addition to introducing mega-lines like Christian Louboutin and Azzedine Alaïa to the American market.

The 10 Most Shocking Fashion Moments of 2019

5. Billy Porter’s tuxedo dress

Porter made a major splash on red carpets throughout 2019 with his gender-fluid style. But his hands down, most memorable look was the Christian Siriano-designed gown-slash-tuxedo getup that he wore to the Oscars. The custom velvet number included a strapless frock, a ruffled button-down and a pristine jacket. While the Pose actor didn’t take home any statues that night, he was riding high off his Emmy win for lead actor in a drama series, making him the first openly gay man to take home that award.

The 10 Most Shocking Fashion Moments of 2019

6. Karl Lagerfeld’s Death in February

Regardless of how you really feel about fashion, everyone was saddened by the loss of Karl Lagerfeld, the incredibly impactful designer who spent 36 years at the helm of Chanel, all while he worked as the creative director of Fendi for a casual 54 years. Lagerfeld also ran his own namesake brand, was an active photographer and was a proud cat dad to the Instagram-famous Choupette.

The 10 Most Shocking Fashion Moments of 2019


Not only did Meghan become a mom this year, but she also added fashion editor to her CV when she was invited to guest edit the September issue of British Vogue. In it, she featured 15 women who she considered to be “forces of change,” including actress Jameela Jamil and author Chimamanda Ngozi Adichie. Sadly (for us), the ever-humble duchess did not appear on the cover. “[S]he felt that it would be in some ways a ‘boastful’ thing to do for this particular project. She wanted, instead, to focus on the women she admires,” Vogue UK editor in chief Edward Enninful explained in a statement via People.

Katie looks like she’s ready for fall season while out in New York. Tap for details #KatieHolmes

8. Katie Holmes’s bra under a cardigan

After the Dawson’s Creek star stepped out in a Khaite cardigan and matching knit bra this past August, she became an overnight fashion celebrity. Holmes’s bra and sweater (which together cost more than $2,000) sold out within the hour that these pics hit the web, and search volume for Khaite increased by 217 percent. As for our thoughts on the matter? A cashmere bra isn’t the most practical fashion purchase, but it just might be the sexiest loungewear out there.

The 10 Most Shocking Fashion Moments of 2019

9. Kim Kardashian’s incendiary shapewear line

Kim Kardashian’s biggest launch of the year was a shapewear brand that she developed after years of being photographed in the slinkiest dresses possible. The only issue? She named the line Kimono (and trademarked the word) without realizing that she was culturally misappropriating a traditional Japanese garment. After plenty of backlash, Kardashian apologized for the snafu and renamed the range Skims.

The 10 Most Shocking Fashion Moments of 2019

Gilbert Carrasquillo/ Getty images

10. Lady Gaga’s red carpet disrobing

As one of the hosts of the Met Gala, Gaga was, of course, going to show up. What we didn’t expect was to see her debut four totally different outfits in a matter of moments. This past May, the singer and A Star Is Born actress arrived in a voluminous hot pink gown and brought her longtime costume-designer-turned-high-fashion-designer Brandon Maxwell as her plus-one. She shed that dress to reveal a more modest black ballgown, which Maxwell took a scissor to, revealing a slinkier hot pink frock. For her final trick, Gaga stripped down to a bedazzled bra, undies and fishnet tights. Now that, ladies and gents, is how you make an entrance.