The Most Cringe-Worthy Fashion Moments in Presidential History

Contrary to Kanye West and Donald Trump’s beliefs, not anyone can be president of the United States. The job demands applicants who are intelligent, charismatic, and have solutions to foreign affairs beyond building a “yuuuge wall.” The one thing he or she doesn’t have to be? Stylish. Sure, we usually see our nation’s leaders sporting dapper suit after dapper suit; however, many of them have fallen victim to some serious faux pas (both sartorially and in terms of their grooming). For your viewing pleasure, we’ve searched the web for the eight worst fashion moments in presidential history.

1. Obama’s khaki suit

Obama wearing a tan suit

Obama’s suit is pretty bad. | Alex Wong/Getty Images

A far cry from a spiffy black tuxedo, a tan suit tends to have casual and cheerful connotations: Easter Sunday, your daughter’s college graduation, a summer wedding. Holding a press conference for serious worldly matters in Russia and Syria? Not so much. Look, Obama, we love when a fashion-forward guy takes a sartorial risk — especially when the gent in question is as highly photographed as our commander in chief. But sporting a lighthearted suit to such a somber press conference merits a slap on the wrist. Here’s a tip for any presidential hopefuls out there: Only opt for sunny khakis when attending fun, fluffy events (like dancing the tango in Argentina).

[Editor’s note, 4/11/2016: An earlier version of this article stated that President Obama danced the tango in Cuba. It has been updated to reflect that he danced the tango in Argentina.]

2. Clinton’s booty shorts

Bill Clinton pauses a moment while being asked about former White House intern Monica Lewinsky

Bill Clinton really doesn’t need short shorts. | Stephen Jaffe/AFP/Getty Images)

Who wears short shorts? The 42nd leader of our country, that’s who. Unless you’ve been living under a rock since 1998, you know that Bill Clinton’s reign was coupled with a few scandals. But Clinton in running shorts that are shorter than any teenage girl would dare to wear doesn’t make anyone happy: not Hillary Clinton, not Monica Lewinsky, and certainly not us. Sigh, if only Clinton knew the “shorts-must-be-as-long-as-your-fingertips” rule that most middle school students were coerced to follow, then the world wide web would be a better place. Or, if  he really felt the need to bare it all, invest in a personal gym! Not even the annoying guy who hogs the treadmill deserves to see this.

3. George W. Bush’s Texan tragedy

George W. Bush

Even George W. Bush isn’t immune to making a fashion faux pas. | Chip Somodevilla/Getty Images

Some fashion faux pas — presidential or not — are bad but we can deal with them. This number from George W. Bush? Painful to look at. Are we the only ones cringing? No? Good. We get it, Bush: You’re from Texas. And while we’re totally fine with your Texan pride, please take it down a few notches. Between the cowboy boots and hat, this getup is straight-up costumey. If the hoedown-ready attire isn’t bad enough to land a spot on our worst dressed list, we can’t help but smirk at the minuscule sunglasses and carefully draped scarf. Diva alert!

4. Reagan’s athleisure moment

Former U.S. President Ronald Reagan and First Lady Nancy Reagan

Presidents shouldn’t hop on the athleisure trend. | Ronald Reagan Presidential Library/Getty Image

Anyone with a busy schedule and a penchant for their Netflix queue is bound to love the athleisure fad. We (and most likely you, too) thank the fashion gods regularly for making it OK — and even cool — to sport sweatpants out and about. But not even the biggest loungewear fanatics can get behind Ronald Reagan’s take on this trend. Where did he go wrong, you ask? It’s all in the shirt and shoes. Nobody would blame the late president for relaxing in a matching sweatshirt and pants combo. Actually, it would be endearing to see Reagan snuggled up in his cozy clothes on Air Force One. But a tucked-in dress shirt and brogues? Who was he trying to fool? This look was awkward and he knew it.

5. Lincoln’s too-high topper

Abraham Lincoln

Abraham Lincoln’s fashion mistake? His overly large hat. | Hulton/Archive/Getty Images

Scheming up a signature look is a great way to distinguish yourself from the bounty of other, equally-stylish guys. But that doesn’t mean that the selected signature piece is a surefire fashion win. Case in point: this president’s statement hat. Sure, we all love Abraham Lincoln for his legacy and iconic appearance, but can you imagine if you saw someone with such a large hat today? Oh wait, we have — Pharrell. Some may call it kitschy, but we prefer the phrase “sartorially peacocking.” A sleek derby cap or fedora would’ve made a statement with less peacocking, Abe.

6. Carter’s cardigans

white house

No one should have allowed Jimmy Carter to leave the White House in this outfit. | Karen Bleier/AFP/Getty Images

Everyone has a fashion role model. Jimmy Carter’s, for example, is clearly Mister Rogers. The signature collection of punchy cardigans worked for the beloved television star, but we can’t say the same for the 39th president. Sure, a chunky, button-down sweater works for your grandpa and elderly next door neighbor. But on the president of the United States? It looks homely. And we have a sneaking suspicion most commanders in chief don’t want to be described as “homely,” especially when delivering a fireside chat about some serious issues.

7. Reagan’s beanie blunder

Ronald Reagan

Ronald Reagan makes the list once again. | Hulton Archive/Getty Images

We know, we know. We didn’t want to call out Reagan twice, either. But, man, this is bad. If a former president wore this ensemble today, we’d expect a tabloid magazine to run this on the cover with the headline, “Presidents: Where Are They Now?” The ill-fitted beanie is giving us some major The Deer Hunter vibes, and not in a good way. And what’s up with those tinted glasses? Didn’t he know that colored lenses were only cool for grown men in the ’70s and tween girls in the early-aughts? And let’s not forget to ask ourselves one very important question: If his head is cold enough to wear a beanie, shouldn’t he be wearing some type of jacket?

8. John Tyler’s flowing bow ties

man with a bow tie

John Tyler could not pull off his bow tie looks. | Pixabay

Since what feels like the beginning of time, guys have used ties as a way to add some personality to the ubiquitous suit. Some uses, such as a luxe silk tie from Charvet or a knitted iteration, are great. Others, like that reindeer tie your boss always pulls out for the annual holiday party, are awkward. And then there’s John Tyler. Haven’t heard of him? He was that guy who stepped up to the plate after William Henry Harrison’s unexpected death. While there may not be much to say about Tyler’s administration, his array of ladylike ties are something to talk about. His documented ribbon-like ties that were knotted into neat, girly bows may attract the likes of Gucci’s Alessandro Michele; however, we can’t say it’s exactly presidential. Sure, the bow ties and flaps we know and love today weren’t “on trend” back in the 17th century, yet a silky ascot has more regal connotations.

Follow Kelsey on Twitter @KMulvs