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From Kylie Jenner to Melania and Ivanka Trump, the 10 Most Shameless Fashion Moments of 2019

Alaina Demopoulos
Photo Illustration by The Daily Beast / Photos Getty

For better or worse, fashion is generally a discreet industry filled with off-record dealings and behind-the-scenes power players. This is not a story about that. 

Sometimes, the business that exists to promote good taste and style can find itself in the middle of a complete and total mess. From clout chasers to needless feuds, 2019 saw its fair share of completely shameless fashion moments. Let’s take a look at the 10 most absurd. 

Anna Delvey Hires a Stylist. . .For Court

Once upon a time, a woman named Anna Sorokin—better known as Anna Delvey—lived the New York highlife, made possible through scamming friends, boutique hotels, and banks out of over $275,000. (Her story was immortalized in a viral New York magazine profile.) Unfortunately for Delvey, there is no such thing as a free luxury Moroccan getaway, and the so-called “SoHo Grifter” went on trial this spring for grand larceny. 

The Russian national was ultimately sentenced to four years, but before that pulled off one last con—turning her trial into a runway show. She hired a former Glamour editor to serve as her stylist, though the clothes she pulled didn’t always get to Rikers in town, which led to more than one courtroom meltdown.

James Charles and Tati Westbrook Fight. . .Over Gummy Vitamins

In April, the influencer James Charles did what beauty influencers tend to do—the 19-year-old posted about Sugar Bear Hair Gummy Vitamins on Instagram. Just another day at Coachella, until you realize that Charles has been mentored by Tati Westbrook. She owns Halo Beauty, another supplement brand. 

Instead of talking it out with Charles, Westbrook took to YouTube to air her grievances in a 42-minute long video rant listing all of her former friend’s bad behavior, including his alleged sexual harassment of a straight male waiter. Charles responded with his own tearful apology video. 

The fallout was Shakespearean in its scope. Charles’ YouTube account hemorrhaged 3 million followers, and at different points in the debacle, both parties were deemed cancelled. The only name that emerged unscathed, it appeared, was Sugar Bear Hair Gummy, which reported a surge in interest following the feud.

Melania and Ivanka Trump Go Full Dynasty in London—with a Little Help from a Flying Saucer Hat

Oh, to get a glimpse of the mood board Melania and company prepared for her state visit to London, for which the first lady and Ivanka wore a carousel of truly batshit outfits.

The first lady began her trip to Buckingham Palace dressed like Joan Collins in Dynasty. Then Ivanka wore her Cruella de Vil Halloween costume to a meeting at 10 Downing Street, striding through boo-ing crowds in a Dalmatian print dress.

The Trump family are not known to go quietly, so naturally on her final day abroad, Melania slapped on a fascinator that could double as a UFO and called it a day. Even though the president called Meghan Markle “nasty,” just days before visiting the royal family, Ivanka and the duchess would later attend the same wedding of a mutual friend, Misha Nonoo. Wonder what they talked about!

A Fashion Influencer Pitched Her Own Proposal To Brands for SponCon

Before this year, Marissa Casey Grossman was merely @FashionAmbitionist, a mid-level influencer who worked at Goop by day and posted run-of-the-mill outfit shots by night (and also by day, judging by the lighting in some of the photographs). That all changed this summer, when her investment banker boyfriend planned an elaborate proposal and marriage, which led Grossman on a trip from New York to Paris. All the while, Grossman catalogued the “surprise” event to her fans on Instagram stories, wondering “What is happening?!??!?!” all along the way. 

Turns out, she knew all along. One day into her week-long engagement, a pitch deck started to make the rounds at various marketing agencies. It appears the 13 page PDF was meant to woo advertisers into sponsoring different moments of the “one-of-a-kind proposal experience.” News of the caper broke via an article in The Atlantic that posted while Grossman was in the middle of her event. In an interview with The Daily Beast, a Goop employee distanced the company from Grossman’s antics. Almost immediately after returning from Paris, she stopped working there.

The Case of Kylie Jenner’s “Stolen” Instagram Pose

This summer, Kylie Jenner went on vacation, which she naturally used as an opportunity to pose fully naked, her photo kept PG-13 through strategic hand placement, leg crossing, and a gigantic straw hat. The post garnered over 11 million likes, and at least one critic—a woman named Amanda Ensing, a fairly unknown model who, judging solely by her Instagram bio (“Your potential is endless”), seems nice enough.

A month before Jenner’s vaycay, Ensing herself demonstrated a similar aptitude for sitting around on vacation naked in a straw hat. To Ensing, this meant Jenner had clearly “copied” her pose, and she commented, “This photo looks awfully familiar.” The mogul had no time for plagiarism accusations, responding, “from the words of Kim K ur not on my mood board but i did get my inspo off Pinterest.” Translation: Ensing’s aesthetic is quite basic, and this is all so tiring. 

Kim Kardashian Turns Alice Johnson Into an Ad 

Last year, Kim Kardashian earned genuine kudos for her efforts lobbying for the release of Alice Marie Johnson, a 63-year-old grandmother who had been locked in an Alabama federal prison since 1996 over a nonviolent drug charge. It was a truly good deed that did not go unnoticed, even from those who are prone to critiquing the reality star. 

But then Kardashian launched Skims, her line of shapewear that IS NOT Spanx. She tapped Johnson as a promotional face, and ads featured the woman delivering lines like, “This shapewear makes me feel like I can walk into the store, I can pick up something I normally wouldn’t think about wearing, and it’s going to look great on me... This shapewear makes me feel free!” 

Hopefully, Johnson was paid handsomely for her time. 

Joss Sackler Ignores Pretty Much Everyone’s Pleas to Go Away, Returns to Fashion Week

There are plenty of reasons Joss Sackler should have sat New York Fashion Week out this year. For one, a slew of (unnamed) editors told the New York Post they would pass on her presentation, citing the controversy attached to Sackler’s husband, OxyContin heir David. Second, the Post revealed that Sackler tried to woo former addict Courtney Love into her Bowery Hotel runway show with a front row seat and $10,000. (Love declined, brilliantly.) Finally, Sackler’s offerings—namely, a vomit green tote bag that retails for $1750—just plain aren’t cute. 

But the show went on as planned, with many attendees telling The Daily Beast they “weren’t aware” of any “political” connections to the Sackler name. As one stylist said, while waiting in line, “You should be able to subtract yourself from your family and be your own person, otherwise we would all be ghosts of our family’s past.” 

Gigi Hadid Puts Her Body on the Line to Stop Chanel Crasher

French YouTuber Marie Benoliel thought it would be quelle surprise when she jumped onto the runway of Chanel’s spring 2020 presentation. Unfortunately for the influencer, Gigi Hadid promptly escorted her offstage, proving that she would be a very competent security guard if this whole modeling thing doesn’t work out. 

In an interview with The New York Times, Benoliel called Hadid “rude,” before backtracking. “I think it’s really funny and I love Gigi and I think now we can be close friends,” she said. As of press time, they are not. 

Barney’s Registry Madness 

When Barney’s announced it was sold on Nov. 1, it kicked off a wave of nostalgia that washed over posh New Yorkers, who remembered the once-giant department store as a bastion of culture and style. The news also began a mad dash for engaged couples who had listed their registries at Barneys to use all their store credit before it expired. 

As The New York Times reported, reps for the storied retailer did not make this fact clear to shoppers, which led to much frustration among some of the city’s most elite happy couples. Talk about stress!

When Trump Met Louis Vuitton 

When Bernard Arnault, CEO of fashion conglomerate LVMH, accompanied Donald Trump to a ribbon-cutting ceremony at the new Louis Vuitton factory in Texas, fashion critics held their breath, awaiting an angry Twitter mob or calls for a mass boycott of the luxury French brand. But instead... mostly nothing happened.

Only Louis Vuitton’s creative director of womenswear, Nicolas Ghesquière, protested, via an Instagram post which read, ““Standing against any political action. I am a fashion designer refusing this association #trumpisajoke #homophobia.” From his colleagues at LVMH fashion houses like Givenchy, Dior, or Marc Jacobs? Silence. 

Few customers seemed to care, too. Minus a few bitchy tweets about Louis Vuitton bags being gauche, the industry stomped on.

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