“Undone (The Sweater Song)” by Weezer.
Those Shoes, The Eagles
Boot-Scootin’ Boogie, Brooks and Dunn
Your Brand New Leopard Skin Pillbox Hat, Bob Dylan
White Boots, Stevie Ray and Jimmy Lee Vaughn
The Wedding Present -My Favourite Dress
Long Black Veil by (among others) Johnny Cash
Soulful Dress, Marcia Ball, is kind of a “hide your boyfriends” strut about how she’s gonna be some hot stuff in her soulful dress.
Sharp Dressed Man, ZZTop
High Heeled Sneakers, Wilson Pickett, or somebody 
“I Bought You the Shoes (You’re Walking Away In)”–Al Kooper
“Slit Skirts”,–Pete Townshend
“Don’t Let Go The Coat”–The Who
“Led Boots”–Jeff Beck
“Blue Jeans Blues”–Various artists
Shorty Long - Devil With A Blue Dress
Marilyn Manson - Dope Hat
One of my dad’s favorites: Something in Red by Lorrie Morgan.
“He wore tan shoes with pink shoelaces
A polka vest and, man o man,
He wore tan shoes with pink shoelace
And a big top hat with a purple hat band!”
Coat of Many Colors – Dolly Parton
My coat of many colors
That my momma made for me
Made only from rags
But I wore it so proudly
Although we had no money
I was rich as I could be
In my coat of many colors
My momma made for me
**A White Sport Coat And a Pink Carnation ** by Marty Robbins, I think.
Girls in Their Summer Clothes - Bruce Springsteen
Underneath Your Clothes - Shakira
The Emperor’s New Clothes - Sinead O’Connor
Hell of a Hat - Mighty Mighty Bosstones
Goody Two Shoes - Adam Ant
Best Sunday Dress - Hole
Fuck Me Pumps - Amy Winehouse
*I want a girl with a short skirt and a loooooong jacket… *Cake
Not to mention “Uniforms” on the same album.
A couple of ones by Depeche Mode
New Dress - “Princess Di is wearing a new dress …”
Dressed in Black - “But oh what can you do when she’s dressed in black”
Blue Dress - “Put it on and don’t say a word”
How Do I Look? (1933)
“When I chose brand new clothes
The gang said I was nifty
But if she should disagree
I’ll sell the works for eighteen fifty”
Top Hat (1935)
“I’m…Puttin’ on my top hat
Tyin’ up my white tie
Brushin’ off my tails”
Breakin’ In A Pair Of Shoes (1936)
“Should I dance, take a chance
Ouch!..My toot-sies”
An Old Straw Hat (1938)
“Sing hi-ho the merri-o!
What’ve you got to lose
Get an old straw hat
A suit of overalls
And a worn out musty
Rusty dusty pair of shoes”
When The Mush Begins To Rush Down Father’s Vest (1940)
(aka When The Soup Begins To Droop Down Father’s Tie,
When the Hash Begins to Dash Down Father’s Coat)
A Zoot Suit (1942)
“I wanna zoot suit with a reet pleat
And a drape shape and a stuffed cuff
To look sharp enough to meet my Sunday gal”
[nitpick]And a big Panama with a purple hat band.[/nitpick]
Sharp Dessed Man by ZZ Top
“Hot Pants” by James Brown
“Bell Bottom Blues” by Derek and the Dominos
“Homburg” by Procol Harum
If I Had a Million Dollars- Barenaked Ladies
"…If I had a million dollars, I’d buy you a fur coat. (But not a real fur coat; that’s cruel)…
…If I had a million dollars, I’d buy you a green dress (But not a real green dress; that’s cruel).
There’s really a group called the “Ass Ponys?” Wow, I’m old.