Donald Trump's Biggest Fashion Fails

Donald Trump probably overheard country legend Dolly Parton when she famously said, "It costs a lot to look this cheap!" After all, this is a guy who can fork over $8,000 for a classy-looking suit yet resembles someone who slept on the street with it. Somehow, he's able to crease those threads to the point where onlookers suspect an anatomic turnaround had occurred, while formalwear pundits dismiss his attire as baggy, among the kinder references to his look. Considering he's married to a fashion-savvy former model and has a daughter who's a fashionista in her own right, it's odd that he doesn't follow their examples.

Trump would otherwise have a hard time finding decent fashion designers, many of whom lean left and don't take kindly to his views and behavior. But that's hardly impeded his options as the former president prefers his own wardrobe line and a short list of brands. "I wear Brioni suits, which I buy off the rack," he penned in his book "Trump: Think Like a Billionaire" per The New York Times. Despite Brioni's reputation for quality and luxury, critics state that choice hasn't helped Trump one bit. 

"He looks like an overblown cartoon, a caricature of himself, a dog that is all bark and no bite," declared writer Eddie Hayes in the Daily Beast. "His style, like himself, is overblown, garish, and completely lacking in substance." It should be noted that such barbs don't merely stop at what he wears.

Donald Trump has limited himself to his choice of suits, either wearing a line that bears his name or labels like Italy's Brioni and Brooklyn-based Martin Greenfield Clothiers, the latter renowned for dressing political figures that include Barack Obama and Michael Bloomberg. But while few negative comments have been uttered about how those two personalities look in suits, one custom clothier in New York hasn't been shy in her critique of Trump. "He wears very expensive suits," said designer Shao Yang, founder of her own operation The Tailory, to The New York Times. "But I don't think he's very modern with his dress. It's making him look a lot shorter and a lot wider."

Detroit Free Press style writer Georgea Kovanis claimed Trump's dumpy, ill-fitting look underscores his difficulties in paying attention to detail. "The suits also serve as a reminder that to many people, Trump's candidacy itself simply isn't a good fit for the party or for the country," she wrote.

But designer Ezra Paul Lizio-Katzen stated there is a method to Trump's fashion madness, in that his baggy outfits not only hide his paunch but also hearken to a conservative look from the '80s, the heydays of the Reagan administration. "He's a politician, and like most politicians, he purposefully doesn't want to dress too fashion-forward and risk looking out of touch with 'middle America,'" Lizio-Katzen wrote in a blog on his Ezra Paul website.

During Donald Trump's 2016 presidential run, campaign manager Kellyanne Conway — herself no stranger to controversy — mused about why the media wasn't covering her boss's trademark combover. She got more than she bargained for when the media mercilessly obliged. Vanity Fair called Trump's hairstyle an "inanimate object that straddles his scalp like a dead furry lobster." And "Jimmy Kimmel Live" host Jimmy Kimmel poked fun at a video of Trump's hairdo flying out of control in a wind gust. "This is why Darth Vader had the good sense to wear a helmet," he said.

Why Trump sports such a hairstyle is still a matter of debate, although HuffPost sought answers while poring through images of the tycoon and politician over the years. The '80s saw Trump with a relatively normal dark-haired coif parted on one side. By the late '90s, his hair got lighter, and a frontal swoop revealed signs of things to come. Since then, that swoop was flush with his eyebrows, while a wavy mullet in the back completed the look.

Some doctors believe the change was to hide a scar from a plastic surgery procedure that eliminated a bald patch, although a few suggest Trump's coif was designed to disguise thinning hair. "I do not question Trump's assertion that is 100% his hair," said dermatologist Dr. Paul McAndrews to Men's Health. "I believe it is his hair, I just do not believe that God was the architect of his hairline."

Donald Trump has had his share of unflattering moments in front of the cameras that would make most people turn red with embarrassment. But given that the politician's mug would be at home in a Sunkist orchard, we're not likely to see that happen. Banter abounds over how he gets that citrus complexion, with some reports indicating that Trump altered his skin tone to hide an affliction of rosacea, a skin condition that causes chronic redness. 

Trump once blamed his prison jumpsuit shade on bad lighting, despite rumors that he applies his own foundation, employs a makeup artist, and even flops onto a tanning bed to create that appearance, which the White House denied. An aide said to The New York Times that Trump's epidermal layers were blessed by "good genes." But whatever he uses, sometimes the method backfires, rendering the former president to occasionally resemble a melting Oscar statuette, as was the case at an Iowa rally in January 2024. "Name this foundation shade," joked The Lincoln Project, an anti-Trump political action committee, on X (formerly Twitter).

That Trump, for all his riches, doesn't opt for a better cosmetic alternative mystifies his critics who continue to laugh at his expense. "I suppose that Trump could look worse, but it wouldn't be easy," noted psychologist Dr. David A Lustig on X. "You'd think that a claimed billionaire could hire a makeup artist who wouldn't make him look like a dirty old shoe."

Probably the most radical fashion accessory that Donald Trump introduced was the signature red MAGA (Make America Great Again) hat, which many believe crosses the line of good taste. "Well, for a start any kind of red baseball cap is now a no-no," noted a writer in GQ. One investment boss said that his London high-tech finance company forbids employees from wearing baseball caps altogether. "Clothing reflects shared values and norms," said Alex Livanis to the Financial Times. "The formality encourages a sense of respect for our clients and our team internally."

But those who can't stand the MAGA hat claim it's anything but a fashion statement. "The hat has become a symbol of us vs. them, of exclusion and suspicion, of garrulous narcissism, of white male privilege, of violence and hate," said Washington Post fashion critic Robin Givhan. "For minorities and the disenfranchised, it can spark a kind of gut-level disgust that brings ancestral ghosts to the fore."

It's a divisive wardrobe item that's sparked feuds between everyone from working stiffs to celebrities. Kim Kardashian famously argued with then-husband Kanye West over the MAGA hat he wore to a Trump meeting. And actor Daniel Radcliffe blasted former NFL great Tom Brady for donning the controversial cap. But there's no doubting the importance of the lid during Trump's 2016 presidential run. "The whole campaign can be summed up in his collected Twitters, and that ball cap," noted CNN commentator Douglas Brinkley.

An obsession with size has long dogged Donald Trump, from 2017 inauguration crowds to his pelvic package, anecdotes gleefully mocked by former president Barack Obama at the 2024 Democratic National Convention. But the media has also had a field day pumping up something else that hangs full frontal, albeit much more visibly, namely his tie. "It dangles all the way down to — well, down to a part of his anatomy that Trump mentioned during the campaign, prompting CNN to run the unforgettable headline, 'Donald Trump defends the size of his penis,'" wrote The Guardian fashion writer Hayley Freeman. "Feel the pride, America."

Ever since his days on "The Apprentice," Trump has draped his tie below the beltline, defying conventional men's clothier wisdom that the tip of a tie should be flush with the waistband or belt buckle. "Like so much else about Trump, the ties are tacky signifiers of wealth and power: shiny, expensive and tasteless," noted Newsweek scribe Alexander Nazaryan. "But a red power tie, I can handle. The length of that tie, I cannot."

Longer ties are also harder to control, especially in a windy situation, which Trump experienced after deplaning in Indiana in December 2016. His red suit accessory flapped wildly in the gale, revealing yet another tacky Trump remedy that failed to keep the thing together and in place: two pieces of Scotch tape on its underside.

Donald Trump has broken a lot of fashion etiquette rules, including the basics surrounding how to mix and match his outfits. That was evident when he met Senator Tim Scott for a chat at the White House in September 2017, spawning an image that went viral regarding his clothing options. "During a meeting with Tim Scott, Trump wore a blue suit jacket with black suit pants, completely unaware of the error he made," wrote tech entrepreneur Christopher Bouzy on X. "He looks like he got dressed in the dark," said stylist Cristina Pearlstein to Yahoo! Lifestyle. "It seems as though the president simply grabbed a pair of black pants, believing they were blue."

What has disturbed some fashion-conscious scribes is that Trump is either unwilling to listen to advice regarding his attire or his handlers are afraid to bring up the subject. "People laughed when the president wore a blue jacket and black pants, but think about what the mismatch meant: Did no one close to him tell him?" asked The Walrus writer Stephen Marche. "Maybe no one could tell him."

Italian clothier Lanier has offered some "perfect broken suit" solutions for people like Trump with mix-and-match issues. Tailors at the establishment suggest that a blue blazer would work well with gray pants or even khakis. "It's crucial to learn how to combine all these elements and avoid unpleasant mixes," said the company on its website.

Donald Trump has frequently alluded to morphing his presidency into king status, but when he met actual royalty, he came off looking more like a court jester than a would-be monarch. June 2019 saw Trump venture to London for an audience with Queen Elizabeth II, whose opinion of the statesman was later revealed to be far from impressive.

The queen, who was normally an empathetic sovereign, likely didn't give him any brownie points for his attire on the night of a posh, white-tie banquet at Buckingham Palace. Those who preoccupy themselves in the art of royal watching noticed his pants didn't drape over the shoes, the waistcoat and the jacket sleeves were too long, and the suit lacked a pocket square. "The fact that Trump doesn't own a tailored tuxedo is the ultimate proof that he's nowhere near as rich as he claims," noted Pajama Patty on X. "You know, they make tuxedos that fit unless the look you're going for is either 'bloated penguin carcass' or 'just ate the queen,'" declared New York writer Lee Papa, better known as The Rude Pundit, on X.

If Trump were ever to don formal wear again, tailor Ezra Paul Lizio-Katzen didn't mince words. "My advice would be go on a diet, honestly," he said to the Washington Post. "It's like [former New Jersey governor] Chris Christie. I can't make the suit look good on Chris Christie, either."

President Donald Trump has sometimes backpedaled on previous decisions, such as quashing a directive that separated children from undocumented, border-crossing parents. But more ribald observers have insisted that Trump once applied that same mentality to his wardrobe at a Republican gathering in Greenville, North Carolina, in 2021, claiming he showed up at the event wearing his pants a la Kriss Kross, as in backward. An apparent lack of a fly and the way his trousers creased at thigh level were cited as evidence for such an assertion, prompting fact-checkers to scurry to their laptops to verify. In the end, investigators like Snopes examined several images of Trump and dramatically concluded, "As such, we rate this claim as 'False.'"

That didn't stop the late-night TV circuit from having a laugh, anyway. "At the very least, his tailor should be impeached," declared James Corden on "The Late Late Show." "It looks like he bumped into something and his pants deployed in an airbag," added Tonight Show host Jimmy Fallon.

However, it turns out that fabric wrinkles were a growing concern during Trump's 2016 presidential bid. Former campaign manager Corey Lewandowski said that campaign spokesperson Hope Hicks frequently steamed the pants of their future boss, sometimes while wearing them. On occasion, even Lewandowski handled the steamer. "If that's part of my job as a campaign manager, I do it all," he said to CNN.

While critics slam Donald Trump for his ill-fitting suits, a few believe his golf wardrobe should also be buried in a sand trap. When on the links, Trump almost always wears a white polo shirt with fancy golf shoes and white or dark blue slacks, which one scribe dismissed as too wide and too long. "It gives him a fairytale look, like he might be able to take off, or sail across an ocean using just what he's standing up in," ruefully snorted The Guardian.

With Trump's shirt tucked in while golfing, others noticed how high he hikes his waistband. "If he pulls [his] pants up [any] higher, they're going to cover his nipples," noted one wag on X. Some images of the president were so unflattering Trump declared that someone used AI to degrade his looks by expanding his belly (via The Independent). As it turned out, he was correct about the alterations; Snopes revealed one image had Trump's face digitally placed over that of equally rotund golfer John Daly.

Digital manipulation and bad outfits aside, comedians have long had fun with Trump's appearance on the fairways. In 2017, Late Night with Seth Meyers host Seth Meyers teed up a news clip about Trump's refusal to allow media to film him golfing, before showing a still of the flabby president swinging a club. "To be fair, if this is how you look when you play golf, you'd ditch the cameras, too!" retorted Meyers.

Going to great lengths to produce a powerful self-image, Donald Trump has even resorted to stuffing his suit jacket with shoulder pads, a feature made famous on TV dramas like "Dynasty," and one notoriously used by upwardly mobile women during the '80s. But adding that heft before an August 2024 social media interview with Elon Musk didn't do much to elevate those optics. The pads popped outwards once Trump sat down and hunched over to check his smartphone. "Look at the shoulder pads on the jacket tonight!" exclaimed Ron Filipkowski, editor-in-chief at political podcast Meidas Touch on X. "Guy thinks he playing middle linebacker!"

"Trump's extraordinarily bulky jackets seem to be part of his ongoing quest to mask his shape," added Guardian scribe Zoe Williams, "but the shoulder pads that he wore when interviewed by Musk are a sartorial paradox that someone (maybe Ivanka?) should walk through with him."

Menswear writer Derek Guy offered a more technical explanation of why that feature doesn't jibe with Trump's physique, noting that shoulder pads work best when the shoulder line is broader than the waist, resulting in a more authoritative and powerful appearance. "To me, Trump would benefit from a softer shoulder, partly because his natural shoulders are narrow but square," noted Guy on X. "The more padding you add to this, the squarer the shoulder line. In my opinion, heavy padding is best for people with very sloped shoulders, not square ones."