The characters in The Simpsons don’t immediately scream “fashion icon.” However, when viewers look past Barney Gumball’s protruding belly, Cletus’ stained white vest, and Groundskeeper Willie’s workman overalls, Springfield actually has a handful of well-dressed, even stylish, residents.
From suave news anchors and B-list celebrities to school principals and everyday fashionistas, The Simpsons has introduced fans to plenty of smart, sophisticated, and considerate dressers over its 32-season run. Some of these characters are vain and try hard to impress, while others are simply born classy.
10 Ned Flanders
This friendly neighborino is usually seen wearing his iconic pink shirt and green jumper combination, which is easily replicated every Halloween by fans across the globe. Ned’s straight-laced look is so iconic that it has inspired a heavy metal band from Arizona called Okilly Dokilly, whose members all dress up like the Leftorium owner.
One of Ned’s other memorable outfits is his skin-tight ski suit. He tells Homer that it feels like he’s wearing “nothing at all,” irritating him so much that he crashes and lands head-first in the snow. Additionally, Ned’s aqua blue pajamas — complete with nightcap — are very wholesome and mirror his personality as one of The Simpsons‘ kindest characters.
The mascot of Duff Beer is one of the more unconventional dressers in Springfield, largely due to his beer-can belt and bright-red cape. Duffman is based on Bud Man, Budweiser’s superhero mascot, and the two men share a fondness for wearing their underwear over their trousers.
Duffman also sports a Duff baseball cap and has the beer’s logo emblazoned on his chest. Although his outfit is mandated by his job, he wears it well and it’s certain to turn heads.
8 Troy McClure
Everyone’s favorite B-list celebrity and Springfield Heights resident is usually seen wearing a pair of white slacks, a pink jumper over a shirt and tie, and some smart brown dress shoes. The washed-up actor, who was voiced by the late Phil Hartman, was best known for appearing in commercials and educational films — Get Confident, Stupid; and Firecrackers: The Silent Killer — and for his sham marriage to Marge’s sister Selma.
Out of respect for Hartman, the character has been retired and hasn’t appeared on viewers’ screens since season 10. However, Troy’s suave get-up lives on in Simpsons lore, as he consistently makes it to lists of the show’s best characters.
7 Lyle Lanley
This one-time character was integral to one of the show’s best-ever episodes, season 5’s “Marge vs. the Monorail,” written by Conan O’Brien. Monorail ambassador and grifter Lyle Lanley puts on a presentation at a town hall meeting, featuring a compelling song, and convinces the town to build a rapid transit system using their surplus money. Lyle skips town before the maiden journey, during which the poorly-built infrastructure malfunctions and nearly kills Homer, Bart, and the other passengers on board.
Lyle’s business intentions may have been malicious, but his outfit is dapper. Inspired by The Music Man‘s protagonist, Harold Hill, Lyle’s early 20th-century attire is comprised of a red suit with a matching bow tie, a white waistcoat, and a straw hat.
6 Herbert Powell
Homer’s long-estranged brother Herb is essentially a smarter version of the Simpson family’s lovable patriarch — but with hair. Herb, who is voiced by Danny DeVito, first appeared in “Oh Brother, Where Art Thou?” when the Simpsons go to stay with him at his Detroit mansion and Homer ends up designing him a car.
Herb is one of the well-dressed characters in the Simpson family, and certainly the best-dressed of the Simpsons men. He wears an immaculate blue suit and tie when the family first meets him, and later during the unveiling of the monstrous car that Homer has designed, he dons a spruce tuxedo with a tailcoat.
5 Lisa Simpson
There aren’t many eight-year-olds who wear pearl necklaces. Lisa takes cues from her mom’s fashion sense and rocks a simple, one-color dress, which she accessorizes with her iconic pearls. As a very young child, she was usually seen in blue dungarees, and on an outing to church or other formal events, she wears a pink dress with a hat or bow.
Earlier this year, a photo of grown-up Lisa from the episode “Bart to the Future” went viral after it showed her wearing exactly the same outfit as Vice President Kamala Harris wore on the day of the inauguration: a royal purple suit jacket with a pearl necklace and pearl earrings. It’s incredibly uncanny, but the coincidence is just one of many times that The Simpsons has seemingly predicted the future.
4 Hank Scorpio
One of The Simpsons‘ most likable and beloved one-time characters is also one of its most fashionable. Hank Scorpio is an eccentric billionaire and Homer’s boss at Globex Corporation. He wears several different outfits during “You Only Move Twice,” the first episode in which he appears. For most of the episode, he wears a purple zip-up sports jacket over a pink shirt. In one amusing scene, Hank asks Homer to hang his jacket on the wall of the Globex office, which has zero walls and glass all around, much to Homer’s befuddlement.
Later, when Hank is battling the U.S. government with a flamethrower, he sports a suave green turtleneck jumper. Despite being an evil villain and Globex’s president, he still manages to pick some great outfits.
3 Waylon Smithers
Mr. Burns’ loyal lackey is one of the most well-put-together and, ostensibly, fashion-conscious characters on the show. Smithers’ purple bowtie, green blazer, and pristine white shirt are a winning combination.
In his downtime, Smithers is also seen sporting some flashy smart-casual attire, including his orange and green Hawaiian shirt, which he wears when forced to go on vacation in “Homer the Smithers.” He also has a collection of sweater vests and a pink silk dressing gown, which he is shown wearing at home while doing his ironing.
2 Lindsey Naegle
Mensa member, network executive, and jack of all corporate trades, Lindsey Naegle is essentially a parody of corporate America — cruel, self-centered, and ruthless. The founder of Springfield’s anti-youth group and one of the execs behind the Itchy & Scratchy & Poochie debacle, Lindsey dresses flawlessly, and always looks sophisticated and stylish.
Some of her outfits include her blue dress and beige suit jacket combo, her black cocktail dress, worn during a date with Sideshow Mel, and her teal waistcoat, which she wears over a white blouse.
1 Disco Stu
Disco Stu likes disco music. Springfield’s disco-obsessed nightclub owner, Stuart Discotheque, is by far the best-dressed character on The Simspons. Not only does he proudly wear a ’70s suit with pink flames and flared trousers, but he rocks purple-tinted sunglasses, a gold medallion around his neck, and wears his hair in an afro.
His most outrageous fashion statement ever was his custom-made platform shoes that contained goldfish. However, this footwear indulgence was short-lived because, as Homer pointed out, the fish were dead. Stu may dress impressively, but he’s unabashedly vain and is often seen checking himself out in a mirror or hitting on married women.