Inappropriate Outfits Politicians Have Been Caught Wearing

Content warning: The following article features instances of racism.

Politicians are supposed to represent the people and dress according to the standards of their profession. For most political figures, simple, neutral-toned clothing will suffice to keep controversy at bay, while also effectively conveying their identity to the public. As The New York Times posits, "In politics, a dress or a tie is never just a dress or a tie; it is a communications tool." But there have been times when politicians were caught wearing outrageous outfits, be it in office or in their sometimes dubious off-hours pursuits. Gone are the days when there was reverence for those in high places; now we are left to scoff and wonder, "what were they thinking?"

Occasionally we are blessed with a rib-tickling outfit from a politician, such as Bernie Sanders' now legendary mittens ensemble, or, as it's also known, the outfit that launched a thousand memes. But Bernie's sense of style, while somewhat unconventional for a senator, is by no means inappropriate. Who wouldn't want those cozy repurposed mittens on a freezing cold Washington morning?

Yet, for the leaders in this article, their choice of garb was more likely to tickle our gag reflex as opposed to our funny bone. Call the fashion police because many of these politicians weren't dressed to the nines — they were dressed to the nine-one-one.

From the pernicious to the absurd, here are the ultimate inappropriate outfits politicians have been caught wearing.

Justin Trudeau's racially insensitive outfit

Canadian Prime Minister Justin Trudeau is generally regarded as a benevolent leader who is at the forefront of many progressive causes. For instance, in 2016, he introduced a historically significant bill to protect the rights of transgender people, as noted by NBC News. So when he was caught wearing a thoroughly insensitive outfit in resurfaced photos from his teaching days, the public was aghast.

Time obtained a copy of a yearbook from West Point Grey Academy where Trudeau was teaching circa 2000-2001. During an Arabian Nights-themed party, Trudeau wore "brownface" makeup and a turban. Shockingly, he was the only person who attended the party to wear such makeup, and, in an even more damning revelation, this was not the first time he had darkened the color of his skin in a racist manner. "I shouldn't have done that. I should have known better and I didn't. I'm really sorry," Trudeau told reporters, adding that he did not recognize that his actions were racist at the time, as per Time.

But the Canadian leader's decision to wear the highly offensive garb prompted some critics to question whether he is as "woke" as he claims to be. "Is it the one behind closed doors, the one when the cameras are turned off that no one sees?" left-wing politician Jagmeet Singh told The New York Times. "Is that the real Mr. Trudeau? Because more and more, it seems like it is."

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Barack Obama and Tan Suit Gate

President Barack Obama was always impeccably dressed, so it was a major shock when he roused controversy for his choice of attire. In 2014, he sported a light tan suit when he held a press conference on military action against so-called Islamic State. Subsequently, the suit was viewed as inappropriate considering the gravity of the issues at hand. "There's no way, I don't think, any of us can excuse what the president did yesterday," said Republican Peter King, as per NY Mag. What made Obama's choice of suit more questionable was the fact that he once told Vanity Fair, "You'll see I wear only gray or blue suits."

The majority of censure came from the right, and although there was arguably little justification for the outrage, some tried to turn it into a White House scandal. However, Obama was defended by fashion expert Robin Givhan, who told The Washington Post, "That is a conservative two-button suit in a color that is perfectly appropriate for the time of year and the occasion ... Honestly, people are responding like he showed up in Pharrell Williams' short suit."

While the suit made for explosive news at the time, Obama now utilizes the bizarre controversy as a means of comic relief. "I was sorely tempted to wear a tan suit today for my last press conference," Obama quipped in 2017, as per CBS. "But Michelle, whose fashion sense is a little better than mine, tells me that's not appropriate in January." Can Obama joke about the incident? Yes he tan.

Sarah Palin's outfits violated campaign finance rules

Former governor of Alaska, Sarah Palin, was John McCain's right-hand woman during his campaign for the presidency in 2008. Since Palin's entire niche was built around appealing to the working class, the image of her as an ordinary all-American mom disintegrated when she sported outfits worth a small fortune. "I don't think Joe the Plumber wears Manolo Blahniks," quipped Joy Behar on "The View," as per The New York Times.

According to a report by Politico, Palin frequently wore fancy designer outfits, including clothes worth $49,425 from Saks Fifth Avenue and $75,062 worth of attire from Neiman Marcus. Considering that the 2016 Census puts the average U.S. household income at $56,516, Palin was flexing fits worth more than most people earn in an entire year.

In addition to alienating her supporters, the outfits stirred further controversy when it surfaced that her $150,000 wardrobe budget far exceeded campaign finance rules, as noted by The New York Times.

However, Palin argued that the criticism she faced was sexist and suggested that a man wouldn't be similarly targeted for wearing expensive outfits. Speaking with the Chicago Tribune, she claimed, "I think Hillary Clinton was held to a different standard in her primary race. Do you remember the conversations that took place about her, say, superficial things that they don't talk about with men, her wardrobe and her hairstyles, all of that? That's a bit of that double standard."

Boris Johnson's messy jogging gear

J.Lo may be Jenny from the Block, but Bo.Jo is stumbling out the blocks. British Prime Minister Boris Johnson isn't exactly known for being a fashion icon. His inappropriate outfits range from jogging in brogues and a white dress shirt to emerging from his home in a bandana and what appeared to be swimming trunks, prompting a journalist for Insider to dress like him for a week. Moreover, he once ventured outside in a pro-feminist t-shirt that read "A woman's place is in the House of Commons," which resulted in intense criticism considering his past sexist remarks.

When he was hailed the new Prime Minister in 2019, many assumed that Johnson would adopt a more debonair wardrobe, but this was not the case. With his much fabled fuzzy white mane and notoriously indecorous wardrobe, Johnson's choice of attire is most unbefitting of a world leader.

According to The New York Times, Johnson's outfits are reflective of his privilege, but they also challenge the very establishment he epitomizes: "Mr. Johnson lets it all sort of shuffle around," writes Vanessa Friedman, who added that his "schlubbiness is both a product of his privilege and its antidote." If anything, Johnson's anti-image has been incredibly beneficial to his political career, creating the façade of an approachable politician who is a far cry from the stuffy suits at Westminster. Thus, his clothing, although seemingly haphazard, could very well be perfectly curated.

Nancy Pelosi and Chuck Schumer wore Kente cloth

When George Floyd was murdered by a police officer in 2020, the crime shocked the nation and led to mass protests. To honor the memory of Floyd, Speaker of the House Nancy Pelosi and majority leader Chuck Schumer took a knee and wore Kente cloth, which is part of traditional Ghanaian attire. Their rationale for donning Kente stoles was to show solidarity with the Black Lives Matter movement. However, many saw the act as insensitive, performative, and an example of cultural misappropriation.

As a result, Pelosi and Schumer were swiftly criticized. Writer Nanjala Nyabola deemed the appropriation of Kente scarves by white politicians to be insulting and patronizing. "Stop using Africans and African cultures as props to deflect criticism. We are not your props," Nyabola tweeted, as per the BBC.

In particular, Pelosi was targeted for styling her Kente scarf with a bright red suit, thereby buttressing criticism that she was utilizing the traditional cloth as a mere prop. As Doreen St. Félix argued in The New Yorker, Pelosi "chose to wear bright red, evidently to coordinate with the rhombuses of green and blue in the cloth, the fabric swung, giving her an inappropriate swagger." Félix added that while there was nothing inherently wrong with wearing colorful clothes to a somber event, the bright outfit in combination with "assuming a pose that mirrored that of Derek Chauvin ... felt not just misguided but like an outright mockery."

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Alexandria Ocasio-Cortez's Met Gala dress caused a stir

Congresswoman Alexandria Ocasio-Cortez is renowned for her progressive fiscal positions, including her push for a $15 an hour minimum wage and commitment to social welfare initiatives. She is the last person anyone would suspect of being targeted by the left. But when she appeared at the 2021 Met Gala, she felt the ire of progressives.

Ocasio-Cortez caused outrage for her choice of outfit at the elite event, wearing a white dress with the message "TAX THE RICH" written in bright red on the back. While many were initially welcoming of her important political message, some felt that the dress was inappropriate due to the fact that a ticket to the Met Gala costs $35,000 and tables will burn a hole worth anything from $200,000 to $300,000 in attendees' wallets, as noted by The New York Times.

Left-wing writer John Ganz took aim at the outfit in an article for Gawker, calling it "the wrong kind of corniness." He added that it was the exact sort of thing Sacha Baron Cohen would parody in making a statment   It's a Hot Topic-level political expression," he argued. "It's the sort of terrible youth-outreach type stuff that Lena Dunham tried to do for Hilary Clinton ... This is like something Sacha Baron Cohen could've come up with to parody the faux-social consciousness of high society."

On Instagram, Ocasio-Cortez defended the dress, writing, "The medium is the message. Proud to work with @aurorajames as a sustainably focused, Black woman immigrant designer ... The time is now for childcare, healthcare, and climate action for all. Tax the Rich."

Bill Lee caused outrage with his Confederate outfit

Governor of Tennessee Bill Lee is known for his conservative views. For instance, he told Associated Press that he is a staunch supporter of capital punishment, having been responsible for an increase in executions in Tennessee. But while support for the death penalty isn't particularly uncommon among conservatives, Lee's embrace of Confederate symbolism is likely a step too far for even the most hardened members of the GOP.

In 2019, photos of Lee dressed in a Confederate uniform resurfaced. The photo, which was taken in 1980 during Lee's time at Auburn University, featured in a school yearbook, and a separate page contained the troubling caption, "The South shall rise again, right Bill! When the band plays 'Dixie', a tear comes to our eyes. I'd do anything Lee, but she comes first," as per NBC News.

"I never intentionally acted in an insensitive way, but with the benefit of hindsight, I can see that participating in that was insensitive and I've come to regret it," Lee said in a statement obtained by the Tennessean. Although he apologized, Lee's choice of clothing reflected his controversial actions as a politician. For instance, just a few months after his Confederate outfit scandal, Lee was heavily lambasted for signing a proclamation designating a day to celebrate Ku Klux Klan leader Nathan Bedford Forrest, as per Associated Press.

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Desmond Swayne dressed as James Brown -- in blackface

British Conservative politician Desmond Swayne was caught dressed up as legendary singer James Brown when photos of him at a fancy dress party emerged in 2019. The Telegraph published the images, which featured Swayne wearing blackface at a "Blues Brothers"-themed gathering.

To make matters worse, when The Telegraph asked Swayne to explain his choice of costume, he failed to see the grossly offensive nature of his actions. "I am disappointed that people have lost a sense of proportion and a sense of humor and that the things you just can't say and can't do, even if they're done for the best possible reasons," he claimed. "Going to a party and having fun in fancy dress seems now to be something that one has to take great precaution about in these woke times, and we all do unless we want the opprobrium of the great and good." He added that his children called him out for wearing blackface, deeming it racist, yet he failed to recognize or acknowledge the overt racism of the outmoded practice, which has pernicious historical origins, as chronicled by CNN.

Fellow politician David Lammy denounced Swayne's choice of costume and urged Prime Minister Boris Johnson to oust the MP, tweeting, "For those who have been victims of racism there aren't words for how grim it is that Tory MP @DesmondSwayne refuses to apologise for blacking up." Unfortunately, Swayne was not reprimanded over the photo.

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Kamala Harris wore this controversial brand

Vice President Kamala Harris is always well-dressed, usually favoring a snazzy suit and even mirroring a chic outfit worn by Lisa Simpson in one of the many eerie "The Simpsons" predictions. It therefore seems as though Harris is the least likely politician to wear anything that would rouse contention. But she did just that in 2021.

On several occasions, Harris has worn outfits that featured clothes by problematic Italian label Dolce and Gabbana, as reported by The Guardian. Many critics slammed Harris' choice of clothing since the D&G founders, Domenico Dolce and Stefano Gabbana, have a long history of racism, fatphobia, sexism, and even homophobia despite the fact that the designers are both gay. 

For instance, Dolce and Gabbana said that they opposed same sex adoption in an interview with Italy's Panorama Magazine (translated by The Telegraph), leading to widespread reproach and a boycott initiated by Elton John. Since then, the luxury designers have been embroiled in numerous other controversies and trolling antics. What's more, the fashion giants are infamous supporters of Melania Trump, having styled her on numerous occasions, as Newsweek highlights.

Subsequently, fans questioned why Harris continued to airily support such a problematic label. "Someone seriously needs to tell her team about Dolce and their problematic issues with race," an Instagram user argued (via The Independent).

Kyle Biedermann dressed as gay Hitler

Kyle Biedermann, a Republican politician for the Texas House of Representatives, was exposed in 2016 for wearing a derogatory outfit eight years earlier. The Texan's choice of fancy dress costume caused outrage, not least because he deemed there to be nothing wrong with dressing up as so-called "Gay Hitler." The outfit was comprised of a swastika-emblazoned Nazi jacket and pink scarf, which Biedermann wore while photographed doing a Nazi salute.

Biedermann wore the highly insensitive outfit, branded both anti-Semitic and homophobic, at a charity event and attempted to justify his choice of attire by claiming that he took inspiration from an old "Saturday Night Live" skit, as per Chron.

"What would be offensive about that photograph?" he carelessly insisted in an interview with San Antonio Express News. "This whole thing is about political correctness. It's not a problem for me whatsoever." Even worse, Biedermann didn't condemn Hitler when queried about the costume; rather, he was more concerned with emphasizing that he isn't gay. "I am not gay and never have been ... I have an amazing wife," he stated.

Despite Biedermann's nonchalant attitude, there is no denying that wearing Nazi imagery is extremely pernicious and hurtful. As Dena Marks of the Anti-Defamation League told San Antonio Express News, "We have consistently criticized any use of Nazi imagery like this because we believe it trivializes the Holocaust and is offensive to those who have suffered and perished at the hands of the Nazis."

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Donald Trump dressed shabbily when he met the Queen

Meeting Queen Elizabeth II is surely a mighty privilege for any politician. Accordingly, such a momentous occasion requires world leaders to wear the finest attire. Unless that world leader is Donald Trump.

When Trump met the Queen in 2019, he did not make fashion great again. The then-president wore a poorly fitted tux, complete with a bizarrely long waistcoat that barely contained his girth and a tiny jacket that appeared to be several sizes too small. This was in stark contrast to the royals' majestic attire, with the queen decked out in an elegant white dress, matching gloves, and tasteful jewelry that complemented her crown.

Accordingly, many eagle-eyed viewers couldn't contain their bemusement at Trump's unabashedly scruffy outfit. "OK, I was gonna make a joke about how Trump looks like the bit from Young Frankenstein, but, honestly, that's unfair to how well tailored the Monster's tux is," joked one Twitter user, as per USA Today. Regarding the unusual outfit, The New York Times noted Trump's preference for over-sized things in general: ties, suits, and most famously, crowds. The outlet further posited that no one was likely to point out his various fashion faux pas.

This wasn't the first time Trump wore inappropriate clothing, having previously become a living meme for wearing extremely long ties. It seems that Trump's outfits are even messier than covfefe.

More blackface: Faron Hamblin

There is never any justification for wearing the profoundly racist blackface, but Virginia councilman Faron Hamblin didn't get the memo. While many of the problematic outfits in this article were worn by politicians before they were elected, Hamblin decked himself in a grossly offensive get-up while he was in office.

Hamblin proudly boasted about wearing thoroughly racist garb, which included blackface, when he dressed up as musician Randy Watson, one of Eddie Murphy's characters from "Coming to America," and posted his outfit on Facebook. "I went out as the legendary Randy Watson tonight. Give it up for my band Sexual Chocolate," he wrote in reference to the fictional band in the Eddie Murphy film, as screen-captured by WWBT.

When he rightfully faced a major backlash, The Washington Post illustrates that Hamblin failed to see what's offensive about a white person dressing up as a Black person by using blackface. He even compared himself to controversial comedian Dave Chapelle, forgetting that he is an elected government official and not a comic.

However, Hamblin eventually apologized. "In both my personal and professional life, I have always been a friend and ally to the Black community and will use this as a learning opportunity to move forward a better and more knowledgeable person," he claimed in a letter published by Insider.

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John Hickenlooper wore a Native American headdress

Liberal-leaning former Denver mayor and Colorado Sen. John Hickenlooper shocked his Democrat supporters when he was caught wearing traditional Native American garments. Hickenlooper wore the attire at an event called One Shot Antelope Hunt, whose official website features the politician dressed in Native American headgear, as he also hung out with men dressed up as Indigenous women, whom he was required to dance with if he lost the hunting game.

Subsequently, a group of Indigenous women launched the hashtag #DropOutHick and wrote an open letter on Medium calling for Hickenlooper to drop out of the Senate race in 2020. "Former Gov. Hickenlooper's actions are inexcusable and set the wrong example for an elected official," the women wrote. "We ask that he withdraw from the race and that he does the work to educate himself on the legacy of violence and discrimination towards Indigenous women, so that repair and reconciliation might follow." The authors also mentioned that attendees of the Antelope Hunt referred to Indigenous women by using an incredibly derogatory and antiquated racial slur.

Speaking with CPR News, Hickenlooper acknowledged the hurt that his cultural appropriation had caused. "That she [one of the letter's authors] would feel such anguish about it is certainly not good," he said, adding, "It's nothing that I would ever do again, recognizing that I would cause her that kind of anguish."

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Valerie Jarrett wore a groovy outfit

Valerie Jarrett, the former advisor to Barack Obama, was caught wearing an outfit that left us begging her to "oh, behave!" During an appearance on CBS Mornings, Jarrett shared her thoughts on Super Tuesday. But viewers were firmly focused on something else entirely. Jarrett was a dead ringer for Austin Powers, as she wore a purple jacket with a ruffled white shirt and large square-rimmed glasses. Considering that she was discussing some pretty weighty topics on the show, her choice of outfit was inappropriate to say the least. 

Bearing an unintentional likeness to a character who is the object of ridicule makes it immensely difficult to take Jarrett seriously, particularly if said character is a faux British clod. We almost expected Dr. Evil to emerge and thwart the interview, pinkie finger and obnoxious laugh in tow. The get-up inevitably led to an abundance of memes. "If she isn't doing an Austin Powers cosplay, she needs to fire her stylist. Do i [sic] make you want to vote baby?!" tweeted one viewer.

Of course, all jibes aside, Jarrett is free to dress however she wants, but there are times when a groovy outfit doesn't seem quite appropriate, particularly during one of the most tense and important elections in U.S. history. However, Jarrett was able to ultimately poke fun at the bizarre ensemble, tweeting, "I got Austin Powers mojo, baby! Game recognizes game." Perhaps Jarrett was attempting to Austin-empower herself with the unusual fit.