The 40 Most Stylish Moments in "The Simpsons"

Written by James Harris (Dr_TacoMD) and Chris Lewis (@cjameslewis)

In the tiny town of Springfield, there are a handful of budding fashion stars that would put any street style star or A$AP crew member to shame. With more than 500 episodes in 24 seasons, Homer, Bart, and the rest of Springfield's finest fashionistos have had their fair share of stylish moments while navigating the wacky adventures that come up every day.

The Simpson family and the folks they live with are supposed to be a parodied mirror of typical, average Americans. So while the majority of their time is spent in clothes that don't spark the imagination, they all have days and moments when their style gets turnt up. Since 1987, when the show launched, these are The 40 Most Stylish Moments in The Simpsons.

RELATED: The 50 Best Simpsons Episodes

"Bart the Daredevil"
Season 2, Episode 8

Inspired by Lance Murdoch, Bart transforms into Springfield's newest and boldest daredevil. Any ballsy performer worth his salt knows that a flashy get-up is paramount to putting on a heart-stopping show. So when he steps up to jump the Springfield Gorge on his skateboard, he comes correct witih a cape and his signature Bart skull and crossbones logo on a tank top. He never makes the jump, but Bart definitely stunted in this outfit.

"Homer the Vigilante"
Season 5, Episode 11

We don't always give old dudes the respect they deserve when it comes to style, and Springfield retirement home resident Molloy reminds us why we should respect our elders' steez. Dipped in all-black-a'thing, the cat burglar is as sleek as the animal his profession is named after. Just goes to show that, if you have the skills and the steez, you can outsmart an entire town full of dim-wits and yokels.

"Deep Space Homer"
Season 5, Episode 15

A sober Barney looked as fit as he does fresh in his official NASA jumpsuit. With no booze to hold him back, he trained to go to space in a piece that was both utilitarian and stylish. We're not saying that the Adam Kimmel x Supreme jumpsuits were directly inspired by this 1994 episode, but who wouldn't want to go from boozehound to ballin' astronaut...and then back to boozehound again.

"The Itchy & Scratchy & Poochie Show"
Season 8, Episode 14

In a metaphysical satire on television production, The Simpsons, and TV fans, Poochie was a character introduced on The Itchy & Scratchy Show to regain a younger demographic. With his in-your-face 'tude, Poochie's pink snapback, cut-of jorts, and matte black Barraccuda jacket was a fresh addition to the usual style on Itchy & Scratchy. Unfortunately, Poochie's debut performance contributed to the "worst episode ever" and he was sent back to his home planet, dying on the way.

"Homer vs. the Eighteenth Amendment"
Season 8, Episode 18

Battling the G-Man Rex Banner takes cunning and skill, all done with serious style. When Homer finds a profitable way to sneak around Springfield's prohibition laws, he dons a hat that only a true bawse could pull off. His bootlegging operation doesn't last long, but dope style is eternal.

"E-I-E-I-D'oh!"
Season 11, Episode 5

Homer strikes upon a million dollar idea by breeding a tomato and tobacco hybrid plant on his childhood farm. And what good is a farmer if he doesn't rock some solid workwear? Homer's worn-in straw hat and roughly hewn suit means he can farm and sell his goods in the same day. This outfit seamlessly blends utilitarian workwear and an aesthetic that gives off an air of trust, which Homer then exploits by getting them addicted to his goods.

"The Homer They Fall"
Season 8, Episode 3

Bart becomes the coolest dude in school when he rocks the $4 gimmicky utility belt that he copped from Comic Book Guy. But flossing so freely leads to Jimbo, Dolph, and Kearney chasing Bart down to get their hands on the ill accessory. When Bart points out that Jimbo doesn't even have a belt, Kearney points out that Bart's ragging on his cord. Fists are thrown, and Bart ends up not even being able to return to the belt, ending up with a classic case of buyer's remorse.

"The Springfield Connection"
Season 6, Episode 23

Unbeknownst to Homer and Marge, Homer's card buddy Herman is running a counterfeit blue jean ring out of the Simpsons' garage. And while the production is shoddy, the aesthetic is clean. Any evidence of the crime quickly disappears when Chief Wiggum and his fellow officers dip into the goods and start rocking dad jeans like the corrupt bawses they are.

"Colonel Homer"
Season 3, Episode 20

Homer makes the transition from suburban corporate cog to managing Springfield's hottest new country music talent, Lurleen Lumpkin. To fully integrate himself into his new position as superstar manager, Homer starts wearing a white cowboy suit that he probably had custom made by Nudie Cohn. Bolo tie, rhinestones, and fringing on the jacket are all essential pieces to this get-up, and Homer makes it work.

"Dumbbell Indemnity"
Season 9, Episode 16

Moe's on the prowl for some female companionship, so he and Homer hit up the local discotheque. Like the rest of us, Moe knows the merits of a dope kit to wear out when you're looking to meet a lady, so he dusts off his most formal look for the occasion. Unlike Usher, he isn't able to make or find love in the club, but the purple tux does attract the eye of the lovely Renee. Mission: successful.

"That '90s Show"
Season 19, Episode 11

Fueled by the anger and sadness that results from temporarily breaking up with Marge, Homer channels his anguish into fronting the grunge band Sadgasm in the '90s. Complete with existential forlorness is the grunge look that Homer pioneers. The scraggly hair, plaid flannel, and long sleeve T-shirts under short sleeve T-shirts become the signature style of the decade, all thanks to Homer's musical genius.

"The Man in the Blue Flannel Pants"
Season 23, Episode 7

Homer scores the job of a lifetime as an account executive of the Springfield Nuclear Power Plant. With the job comes a certain manner of dressing, as Don Draper, Roger Sterling, and all their fellow boozy womanizers have taught us in Mad Men. Homer ditches the white polo and dad jeans for the charcoal suits and hats that the ad men of the '60s were famous for.

"Flaming Moe"
Season 22, Episode 11

With the help of Whalon Smithers, Moe Sizlack turns his shithole of a bar into Springfield's most successful gay bar, beating out The Leage of Extra Horny Gentlemen for the top spot. Moe's is soon attractive some of the most fashionable men in the town, and it becomes a veritable who's who of stylish dudes and fashion industry insiders.

"The Greatest Story Ever D'oh-ed"
Season 21, Episode 16

Admit it: when Americans travel abroad, we stick out. And we're damned proud of it! Lest anyone think the obese, boorish, idiotic Homer is not an American, he dresses up in full Ol' Glory regalia so no one is mistaken. Is there anything more stylish than patriotism?

"New Kids on the Blecch"
Season 12, Episode 14

In a strange twist of events, Bart, Milhouse, Nelson, and Ralph are recruited to form a boy band called the "Party Posse." With their gear that's both wholesome and heartthrob, the boys perfectly encapsulate both the fashion and music on the early 2000's. Seeing this episode definitely freezes a moment in time, and also makes us appreciate how far Justin Timberlake has come.

"The Day The Earth Stood Cool"
Season 24, Episode 7

Homer is a middle-class white guy who loves cheap beer, slacking off, and going on wacky adventures. In other words, it only took a few fashion transformations for him to become a full-fledged hipster. By adopting the latest insufferable style trends, Homer joins the ranks of cool kids who have flocked to Springfield, which, of course, makes it played out and not cool. It's a vicious cycle.

"Team Homer"
Season 7, Episode 12

There's nothing like a good ol' fashioned blunt statement made on a T-shirt. When Bart unveils his "Down With Homework" shirt, it incites a student riot, which results in Springfield Elementary instituting school uniforms. Just another example of how fashion can get ratchet and make change.

"A Milhouse Divided"
Season 8, Episode 6

When Kirk Van Houten seeks to drop his debut club banger, "Can I Borrow a Feeling?" he knows that image art can make or break an artist before the needle even drops. Cue the provacatively opened shirt, purple vest that we assume is made of leather, and single thin chain. Along with his golden pipes, Kirk is set to go platinum and challenge A$AP Rocky as the No. 1 fashion killa.

"Homer's Barbershop Quartet"
Season 5, Episode 12

In a take-off on the Beatles' final public performance, the Be Sharps reunite on top of Moe's Tavern. Like the famous foursome, the barbershop quartet is decked out in stylish gear, with Home rocking the red peacoat originally donned by Ringo, and Barney in the fur number that John Lennon wore. A bittersweet moment, as the Be Sharps broke up immediately following this performance. But the guy who had the worst day was the Human Fly, who was up all night dying his underwear.

"Homer the Great"
Season 6, Episode 12

When you're the leader of Springfield's illuminati-esque Stonecutters, you're gonna be rocking some serious dictator gear. Robes, giant shoulder pads, patches as regalia, and an enormous headpiece are all part of the deal. The power steez goes straight to Homer's head, leading to his downfall, but for a second there he was the best dressed supreme leader in the world.

"Mom and Pop Art"
Season 10, Episode 19

Milhouse hates his flood pants, thinking that his ankles are too exposed and vulnerable. But then, a flash flood caused by Homer clogging up all the storm drains in town makes him realize that the pants are perfect. His ankles are wet, but the cuffs are bone dry. All of a sudden, everything's coming up Milhouse!

"The Cartridge Family"
Season 9, Episode 5

What would Homer's life be like with a gun? He'd be surrounded by a go-go dancing Marge, and his fancy kit would include a monocle, tophat, and a boutonniere that takes his charcoal suit to the next level. We're not saying that getting a gun would bring this fantasy to life—we're just saying that Homer's one well-dressed dude in his ideal world.

"The Otto Show"
Season 3, Episode 22

What's better than throwing on your rock 'n roll leather jacket with fringes and tons of memories contained in its natural aging when heading to a Spinal Tap concert? How about finding a can of Billy Beer in one of the pockets? Homer lucks out, and enjoys a cold one (warm one) before heading to the concert where he jams out in his car while Bart and Milhouse enjoy the show.

"Grampa vs. Sexual Inadequacy"
Season 6, Episode 10

Normally, you wouldn't want to buy a miracle libido enhancer from a raving old man, but put that old man in a crispy white suit and all of a sudden you're reaching for your wallet. While selling Simpson and Son’s Revitalizing Tonic, Grampa suits up in his finest garb and instantly sells out every batch he and Homer mix up in the bathtub.

"Scenes From the Class Struggle in Springfield"
Season 7, Episode 14

Mr. Burns doesn't play around with his fashions, and that includes when he's rolling around in the whip. This old-timey driving outfit is quite possibly the only thing that could have upstaged Marge's stunning Chanel dress, and gives him the status to command Marge to, "Fill it up with petroleum distillate, and revulcanize [his] tires, post-haste!"

"D'oh-in In The Wind"
Season 10, Episode 6

When it comes to style, Abe Simpson doesn't get caught up in fleeting trends. In a flashback to Woodstock, this point is proven when he forgoes progressive hippie fashion and opts instead for the timeless suit and tie look. We could all learn a lesson from Abe to stay the style course.

"The Last Temptation of Homer"
Season 5, Episode 12

In 1993, Bart's thick-rimmed glasses cast him into nerdom. Turns out, he was 20 years ahead of his time, pre-dating Kevin Durant, Russell Westbrook, and mad hipsters. This stylish look wasn't appreciated at the time, but as we continue to be influenced by the '90s, it only becomes more and more clear that we should all take style tips from Springfield.

"Secrets of a Succesful Marriage"
Season 5, Episode 22

As the distinguished professor of a class that teaches the secrets to a successful marriage, Homer knows that he needs to wear the sartorial uniform of a learned man. Rather than conforming to professorial norms, Homer reverses the formula by putting tweed patches on a leather jakcet. Don't be surprised if your prof starts rocking this look, since Homer is a certified #influencer.

"Krusty Gets Kancelled"
Season 4, Episode 22

When Krusty's ratings begin losing out to the ventriloquiest sensation Gabbo, his show is soon cancelled. All hope is lost for the klown, until Bart and Lisa begin recruiting big-name celebs to star on Krusty's comeback special. While shmoozing with Hugh Hefner, Bart dons an outfit that mimics the playboy's famous cozyboy look. Bart joins the ranks of the nation's best dressed playboys, and finishes the look off with a classy bubble pipe.

"Who Shot Mr. Burns, Part One"
Season 6, Episode 22

When Springfield Elementary hits upon a large oil patch, Mr. Burns dresses as Springfield Elementary ne'er-do-well Jimbo Jones in order to get a cut of the school's newfound wealth. The black skull T-shirt, blue jeans, and beanie are a youthful look for the decrepit billionaire, but his translucent skin and liver spots are a dead giveaway.

"Radioactive Man"
Season 7, Episode 2

When the filming of Radioactive Man moves to Springfield and castings begin for a local kid to play Fallout Boy, Bart is absolutely set on playing the part. He's told he'd be perfect for the role...if he wasn't exactly one inch too short. So he employs every style trick in the book to appear taller. A vertically striped suit, platform kicks, extra tall hair, and a tiny dog are all for naught, but Bart's sweet mod look (minus the dog) would work anywhere else.

"Bart's Dog Gets an F"
Season 2, Episode 16

NEd Flanders is the first person in Springfield to take part in the latest workout craze by purchasing Assassins. The shoes come complete with velcro straps, a water pump in the tongue, a built-in pedometer, reflective sidewalls, and little vanity license plates (MSRP: $125). Homer of course has to have a pair, as does A$AP Rocky, who copped a pair of Raf Simons 2008 boots for a whopping $1,800. If only Santa's Little Helper hadn't chewed up Homer's pair...

"The Principal and the Pauper"
Season 9, Episode 2

Turns out that, before serving as elementary school principal, Seymour Skinner rocked an awesome leather jacket, had a James Dean 'do, and a "Don't Give a Fuck Attitude" as a biker punk named Armin Tamzarian. It was a far cry from the uptight beauracrat he became, but after the real Seymour Skinner re-surfaced in Springfield, it was time for Armin Tamzarian to ride again. Until he hung up his leather jacket and resumed having a stick up his butt.

"Two Dozen and One Greyhounds"
Season 6, Episode 20

Who knew that, besides money and power, Mr. Burns' black, shriveled heart was warmed by fashion? Particularly, clothes made from the body parts of exotic animals. This includes but is not limited to a sweater made from Irish Setter, slippers that originated as albino African endangered rhino, and a vest made of gorilla chest. Through the power of song, Mr. Burns shows us that he's actually Springfield's No. 1 fashion killa.

"King-Size Homer"
Season 7, Episode 7

Homer isn't known for his svelte figure, but when he gains 61 pounds to be able to work from home, he has to switch up his wardrobe accordingly. Luckily, it's not unheard of for big dudes to stay steezy, and Homer takes cozyboy to very advanced levels with a floral muumuu and cape. If you ever become morbidly obese but still want to get street styled, try this look and start racking up the reblogs.

"Stark Raving Dad"
Season 3, Episode 1

In the corporate world of the Springfield Nuclear Power Plant, it's best to blend in with the crowd and count down the hours until you can hit up Moe's. However, after Bart throws in his lucky red cap with Homer's laundry, Sector 7G's laziest worker attracts unwanted attention from Mr. Burns, which eventually lands him in the loony bin. Little did all his critics know that pink would become a popular color for dudes to rock at work circa 2007. #Influencer.