1. Bob Dylan, “Leopard-Skin Pill-Box Hat”
It’s hard to tell what the narrator of this Blonde On Blonde standout despises more: the song’s titular piece of hoity-toity haberdashery, or the cheatin’, no-good woman underneath it. It could be that the singer hates the hat because he can’t bring himself to admit that the woman has done him wrong—in consecutive scenes within the chugging roadhouse number, he finds the object of his affections with another man, but he ultimately places the blame on that darn hat. It’s a status symbol, one that sits on her head “like a mattress balances on a bottle of wine” as it attracts doctors and gold-digging gentleman callers. The vulnerable yet headstrong romantic, meanwhile, just wants to step all over the thing.
2. Jenny Lewis And The Watson Twins, “Rabbit Fur Coat”
Wrapping a melancholy lullaby in a soft, fuzzy layer of metaphor, Jenny Lewis And The Watson Twins’ “Rabbit Fur Coat” uses the titular garment as a symbol of a mother’s pride and obsession with social standing, which stems from an altercation with a rich “girl of less character” and manifests itself in a tryst with the girl’s father in her “mansion house.” But the mother’s refusal to hand over that piece of outerwear has further repercussions, and 20 years later the narrator becomes “a $100,000 kid”—a none-too-subtle allusion to Lewis’ former child-star career. Though she brushes off both that career (“But I’m not bitter about it / I’ve packed up my things and let them have at it”) and her fortune-faded mother (“I hear she’s putting that stuff up her nose / And still wearing that rabbit fur coat”), Lewis acknowledges her own potential hypocrisy, noting what’s waiting for her “when I sell out and leave Omaha” (a nod to the home of Saddle Creek Records, Lewis’ former label as a member of Rilo Kiley): a mansion house and, yes, a rabbit fur coat.
3. Meryn Cadell, “The Sweater”
“The Sweater” is only a song in the sense that King Missile’s “Detachable Penis” is a song; it’s more a rhythmic spoken-word piece with background music. But like “Detachable Penis,” it’s deadpan hilarious. Canadian performance artist Meryn Cadell tells this story in second person, directly implicating every listener in an emotional process described in confessional singsong: You have gone on a camping trip with other people from your (presumably junior-high) class, and your crush object loaned you a sweater, and now you are obsessed with it, in spite of its “slightly goat-like smell which all teenage boys possess.” You are welcome, Cadell says, to lie next to it in bed if you want, “or touch it on your legs or whatever / That’s your business.” But the point is, after obsessing over it for a weekend alone, you are to wear it to school to show everyone how much your crush object cares about you. And if that plan backfires—as it does, in Cadell’s telling—it’s your fault, isn’t it? You’re the one who chose to pretend a discarded sweater was a sign of true love, you silly junior-high-school girl, you.
4. The Lonely Island, “Turtleneck & Chain”
On “Turtleneck & Chain,” the title track of The Lonely Island’s 2011 album, the trio lampoon rap music’s fetish for clothes and jewelry by positing the curious combination of a thin-ass gold chain, a thick-ass turtleneck, and a light beer as a drinkable accessory as the ultimate in badass hip-hop fashion. It’s a trenchant bit of musical satire made all the more effective for legitimately sounding like a badass exercise in Screwed Up swagger, as Andy Samberg, Akiva Schaffer, and Jorma Taccone (with special guest Snoop Dogg) show off sweaters with puffy necks and jewelry that looks “like Cookie Monster flossin’ his mouth.” Never has wearing a thick turtleneck and thin chain while sipping on a light beer sounded so gangsta.
5. Railroad Jerk, “Clean Shirt”
Railroad Jerk was one of the first bands signed to then-fledgling Matador Records, though the bluesy New York band never took off in the way that Superchunk or Pavement did. But the band’s fourth and final album, The Third Rail, is packed full of ornery, fun songs, none better than “Clean Shirt,” an ode to empowering oneself via the laundry. Singer Marcellus Hall, who put out a solid solo record last year, declares that he’s going to pick himself up off the dirt, and then “put on something nice”—something like his “best clean shirt.” It’s maybe not his best shirt overall, but at least it’s clean.
6. Spoon, “The Fitted Shirt”
Railroad Jerk’s one-time labelmate issued something of a companion piece to “Clean Shirt” in 2001, placing its own herky-jerky tribute to a nice button-up in the middle of its breakthrough LP, Girls Can Tell. True to Spoon’s knack for recycling and reinventing the sounds of yesterday for the listeners of today, “The Fitted Shirt” is alternately nostalgic and forward-thinking, its ache for a politer, more stylish era—one which, according to the final verse, may very well be in the future—powered by a hemmed-in power-pop strut. In spite of its seemingly insignificant subject matter, “The Fitted Shirt” can be read as a mission statement for a band that once reportedly instituted a “no beards” policy, an act defined by the crisp, timeless cool of a well-fitting dress shirt.
7. Donovan, “I Love My Shirt”
Reflecting the singer-songwriter’s contemporaneous interest in children’s music, Donovan’s 1969 LP Barabajagal introduced the world to the jaunty naiveté of “I Love My Shirt,” a literal laundry list of a song that also pledges its fondness toward some shoes and a pair of jeans. But it’s the shirt that’s the true focus of the song’s pride, though Donovan holds his tongue with regard to the make, material, color, and any other details beyond the garment’s basic essence as a shirt that he “really loves” and can’t wait to get back from the laundromat. Perfect for a campfire sing-along (the smell from which would necessitate another trip to the cleaner’s), but bad for Donovan’s reputation as the foolish man’s Dylan.
8. Deirdre Flint, “The Bridesmaid Dress Song”
Women who have been called upon to stand up at weddings inherently know things their male counterparts and non-bridesmaid friends can only glean from various pop-culture jokes: Bridesmaids’ dresses are highly event-specific uniforms, usually uncomfortable, expensive, and unwearable in any other context, in spite of the de rigueur bride statement, “It’s so pretty, you’ll definitely be able to wear it again!” Modern folksinger Deirdre Flint knows otherwise, and she turned that cliché statement into a funny epic about a frequent bridesmaid who does find a way to repurpose a particularly ridiculous dress—as an endless source of survival gear, after a rival bridesmaid pushes her overboard during a wedding at sea. Like so much of Flint’s work, “The Bridesmaid Dress Song” is perky, sweet, and even tinged with a saccharine romanticism, but it’s simultaneously deeply acerbic, as any song repeatedly containing the phrase “jumbo butt-bow” must be.
9. The High Numbers, “Zoot Suit”
In 1964, The Who’s manager Pete Meaden persuaded the group to change its name to The High Numbers. The switch happened just in time for the release of its first single, “Zoot Suit,” which Meaden wrote—or rather, appropriated from “Misery,” a minor hit by the Michigan R&B combo The Dynamics. Meaden had hoped the makeover would give The Who added appeal to the burgeoning Mod subculture in England. He was wrong: In spite of lyrics that tout the Mod uniform of “inch-wide tie,” “two-tone brogues,” and a “zoot-suit jacket with side vents five inches long,” the song bombed. After ditching Meaden and reverting to its previous name, The Who became Mod’s signature band—on its own terms and with its own compositions. But not before leaving this hip, grooving paean to sartorial superiority.
10. Brian Hyland, “Itsy Bitsy Teeny Weeny Yellow Polka Dot Bikini”
The two-piece bathing suit named for a nuclear-test site still had the power to scandalize in 1960. However, it began to lose its shock value in June of that year thanks to songwriters Paul Vance and Lee Pockriss. The duo’s cloying composition for bubblegum star Brian Hyland, “Itsy Bitsy Teeny Weeny Yellow Polka Dot Bikini,” reached the top of the Billboard charts the following August, broadcasting the story of a shy girl driven to hypothermia by her revealing beach wear from car stereos and turntables for an entire summer. As the bikini merged into the mainstream in the following decades, Vance and Pockriss’ song became a signpost for shifting cultural taboos, a kitsch object covered in multiple languages and styles, many of which—like Devo’s 1987 take for the Revenge Of The Nerds II soundtrack or Bombalurina’s amped-up Europop version—winked at the leering quality of Hyland’s original.
11. James Brown, “Hot Pants”
Responsible for catalogues of R&B that speak directly to the hips and ass, it’s only logical that pants are the apparel to which James Brown would pay the closest attention. While the refrain of “I Got Ants In My Pants (And I Want To Dance)” deals in metaphor to describe the involuntary motions inspired by Brown’s soulful grooves, “Hot Pants” immortalizes a sartorial statement that came into vogue in the early ’70s. Over chicken-scratch guitars from Hearlon “Cheese” Martin and Robert Coleman and neck-snapping counterpoint from the horns and Fred Thomas’ bass, Brown gives a shout-out to the female members of his audience finding confidence and self-esteem in hemlines that climb higher and higher. It’s a slightly twisted message of empowerment—but if Brown’s eyes aren’t in the right place, at least the song’s heart and The J.B.’s vamping are.
12. The Royal Teens, “Short Shorts”
There’s no accounting for musical inspiration. One minute a guy is cruising down the street in his friend’s car, and the next he spies a pair of girls in cut-off shorts and launches into a multi-decade recording career. So it went for Bob Gaudio, founding member of The Four Seasons and one of the songwriters responsible for “Short Shorts,” the highest charting hit for Bergenfield, New Jersey’s The Royal Teens. It’s an appropriately simple backstory for a song that’s little more than repeated observations about the lengths of shorts and the women wearing those shorts. The resulting song got the band into a recording studio, on the road, and long after Gaudio departed to join The Four Seasons—then The Four Lovers—the song earned The Royal Teens a licensing deal with “Short Shorts” friendly hair-removal product Nair.
13. Mustard Plug, “Thigh-High Nylons”
The great irony of Mustard Plug’s 2-Toned tribute to women’s hosiery is that the song dismisses passing fashion crazes—flower-child haircuts, bobby-soxer footwear, and a time when fur wasn’t murder—while indulging in a musical fad: the third wave of ska that crested with big hits by No Doubt, The Mighty Mighty Bosstones, and Reel Big Fish. Grand Rapids, Michigan’s proudest skanking sons were simply ahead of the curve in 1993, musically and sartorially speaking. Two years later, third-wave ska and the subject of “Thigh-High Nylons”—which frontman Dave Kirchgessner cheekily argues are “all you need, and nothing more”—reached a cultural zenith thanks to a movie obsessed with trendiness: Amy Heckerling’s Clueless. But given the way Alicia Silverstone and her co-stars are styled in the film, it’s Mustard Plug, not the Bosstones, who deserved to cameo in the big concert scene.
14. KC And The Sunshine Band, “Boogie Shoes”
Just before disco became the slick, synthesized, symphonic sound of ’70s decadence, KC And The Sunshine Band was helping keep the genre funky and fun. One of the Florida group’s frothiest hits, 1975’s “Boogie Shoes,” simplemindedly celebrates the joys of putting on boogie shoes, “doing it ’til the sun comes up,” and, um, that’s about it. The song took off two years later after being included in the soundtrack to Saturday Night Fever, where its innocent, heel-kicking joyousness feels slightly out of step.
15. Run-DMC, “My Adidas”
By eschewing the flamboyant stage attire of old-school acts like Afrika Bambaataa, the members of Run-DMC brought hip-hop fashion into the culture’s golden age. Taking cues from Jam Master Jay’s personal, b-boy-inspired style, the trio brought the look of hip-hop’s grassroots into America’s living rooms via King Of Rock and the video for “Rock Box.” Now playing to a wider audience, the trio felt a responsibility to properly represent the multitudes of personalities donning gold chains, track suits, and Cazal frames—they did so by praising the versatility of that look’s signature sneaker. “My Adidas” is more than D.M.C. and Rev. Run bragging about how many pairs of shell toes they have in their closets—it’s the musical footprint of an entire movement. Jam Master Jay’s “My Adidas” beat, meanwhile, still kicks harder than a steel-toe boot.
16. Nelly, “Air Force Ones”
In 2007, Nike brought together Kanye West, Nas, Rakim, KRS-One, DJ Premier, and Rick Rubin for the Grammy-nominated “Classic (Better Than I’ve Ever Been),” a single commemorating the 25th anniversary of its Air Force One basketball shoe. It shouldn’t have bothered: Five years earlier, Nelly recorded the definitive tribute “Air Force Ones,” a song whose sneakerhead obsessiveness made West and Rakim’s awkwardly shoehorned shout-outs seem even more insincere. “I’m just a sneaker pro, I love Pumas and shell toes / But can’t nothin’ compare to a fresh, crispy, white pair,” Nelly raps of his devotion to the iconic staple, which sees him “up in Foot Locker” demanding his preferred sneaker two pairs at a time, in every color from “the limited-edition khaki and Army green” to “the black, and the platinum, and leather gray / Ones in the back and the pair you got on display.” That consumer loyalty bordering on addiction—not to mention the free advertising—doesn’t translate to Nike hooking him up gratis, however, as Nelly admits, “Sometime I get ’em free, sometime I gotta pay.” But considering how quickly Nelly goes through Air Force Ones, Nike would probably go bankrupt if they did.