Mr. Burns - See My Vest
The Sweater by Meryn Cadell
Gypsy Sock by James Gordon, also Sweaters for Penguins
Brand new leopard skin pillbox hat- Bob Dylan
I Love A Man In A Uniform - Gang Of Four
CMC +fnord!
A few more:
Hand in Glove - The Smiths
Hat and Feet - Fountains of Wayne
Big Legs, Tight Skirt - John Lee Hooker
Yup. Their first album came out in 1993, too.
Rancid “Time Bomb”
Sia “Little Black Sandals”
Sufjan Stevens “The Dress Looks Nice on You”
Yo La Tengo “Autumn Sweater”
Fatkid Dodgeball “Brown Sweater”
Shudder To Think “French Tee Shirt”
“Baby’s in Black” by the Beatles.
“Long Cool Woman in a Black Dress” by the Hollies.
My last one:
Bikini Girls With Machine Guns - The Cramps
I’m stretching to include a couple of accessories, but WTF.
Bad Sneakers - Steely Dan
Bell Bottom Blues - Eric Clapton
Brand New Key - Melanie (about rollerskates)
The Fez - Steely Dan
Golden Earrings - The Platters
Green Earrings- Steely Dan
Long Cool Woman In A Black Dress - The Hollies
This Diamond Ring - Gary Lewis
A few more Frank Zappa songs:
Fembot In A Wet T-Shirt
Po-Jama People
The Girl In The Magnesium Dress
Take Your Clothes Off When You Dance
Reaching a bit, but … Roger Ruskin Spear, Rebel Trouser.
The Laundry Cycle by The Bobs. (Dictator in a Polo Shirt, Pounding on a Rock, etc.)
He also recorded Trouser Freak.
And if one looks at the output of the Bonzo Dog Band overall, one is struck by how many of their songs are (at least in part) about shirts, trousers and other articles of clothing. A Bonzo discography reveals such tunes as Trouser Press, Bell Bottom Trousers, Skirts and Button Up Your Overcoat, not to mention I’m Gonna Bring A Watermelon To My Girlfriend, which doesn’t fit here but I like the concept.
Don’t forget Helmet and My Shoes, from their second album, and (checking their website just now) Disappointment Pants off their latest.
I haven’t heard that last song, though. It could be about a tired dog.
Laurie Anderson, “Sweaters”:
*
I no longer love your mouth. I no longer love your eyes. I no longer love your eyes. I no longer love the color of your sweaters. I no longer love it. I no longer love the color of your sweaters*
And, from the same album: “Gumboots”.
Following the rubber boot connection, Billy Connolly had a hit with “If It Was ’Nae For Your Wellies”, but he also recorded “Stainless Steel Wellies” and “Silk Pyjamas”.
For a more traditional Scottish song, we can go with Andy Stewart:
Let the winds blow high,
Let the winds blow low,
Down the street in my kilt I go
And all the ladies say hello
Donald where’s your troosers?
Thought about another one (doubt anyone outside Sweden or maybe Germany has heard of this Swedish industrial/synth band though)
Cat Rapes Dog - Moosehair underwear
“Short Shorts” by The Royal Teens–most remembered, I’m sure, as a Nair ad.
“Alice Blue Gown,” from the musical Irene.
One of my favorite songs ever: Three-Button Hand Me Down by the Faces - from their album First Step.
Pounded on a Rock.
Here are the songs in The Laundry Cycle by The Bobs:
Pounded On A Rock
Signs On The Line
Dictator In A Polo Shirt
Where Does The Wayward Footwear Go?
Share A Load
And here’s a previous thread regarding songs about shoes.