[Rocky]

Didn’t the Beatles have a song: “She’s just a 17. You know what I mean.”

(j/k)

[Grimmy]

Jon Pardi - Dirt On My Boots

https://www.youtube.com/watch?v=gCxbgqyC2Wg

[hercuroc]

https://youtu.be/QgSW9Ipn0OI
Van Halen-Sucker in a 3 Piece

[unclejohncornbread]

Mink DeVille Italian Shoes.

[Tacrolimus1mg]

“Beautiful With You” - Halestorm

I stare at the girl in the mirror
Tee-shirt, torn up jeans, no beauty queen
But the words you sing me
You get underneath me
And all my defenses just fall away
Fall away

I am beautiful with you
Even in the darkest part of me
I am beautiful with you
Make it feel the way it’s supposed to be
You’re here with me
Just show me this and I’ll believe
I am beautiful with you

I stand naked beside you now
No walls to hide behind
So here am I
You see all of my scars
Still here you are
I bare my soul and I’m not afraid
Not afraid

I am beautiful with you
Even in the darkest part of me
I am beautiful with you
Make it feel the way it’s supposed to be
You’re here with me
Just show me this and I’ll believe
I am beautiful with you

I’ve been the strong one for so long
But I was wrong
Does it make you weak if you’re needing someone
I’m not holding back and I know what I want

I am beautiful with you
I am beautiful with you

You want for myself
You get me like no one else
I am beautiful with you
I am beautiful with you
Even in the darkest part of me
I am beautiful with you
Make it feel the way it’s supposed to be
You’re here with me
Just show me this and I’ll believe
I am beautiful with you

The ENTIRE song isn’t about clothing, but it was my first thought.

That and:

“These Boots Were Made for Walkin’” - Nancy Sinatra

[CommerceComet]

Not in the title but this song has those wonderful lines: "And them limey eyes, they were eyeing a prize some people call manly footwear." At 3:47.

London Homesick Blues by Gary P. Nunn

Some others:

Tight Fittin Jeans by Conway Twitty

Old Brown Shoe by the Beatles

Itsy Bitsy Teenie Weenie Yellow Polka Dot Bikini by Brian Hyland

[Fiji Hill]

Men who wanted to look sharp but were not greatly depressed by the Great Depression might wear a checkered suit, fancy vest, polka dot tie and a top hat. Women would wear a gown tied with ribbons, brand-new shoes, a pretty hat and the latest-style gloves.

Annie Doesn't Live Here Anymore--Guy Lombardo & His Royal Canadians (1933)

[Grimmy]

Colt Ford - Workin’ On

https://www.youtube.com/watch?v=yAfc6i63OY0

Good song. Has a passing mention of jeans, so sneaking it in.

[certrtwngnut]

Put Your Shoes On Lucy Don’t You Know Your In The City.
1949 Nellie Lutcher

[Michael.SF.]

Joe Cocker did a classic cover of this, but this is the original from Randy Newman, back when he was good and not so cartoonish:

Leave Your Hat on -- Randy Newman

[philman_36]

Brian Hyland - Itsy Bitsy Teenie Weenie Yellow Polka Dot Bikini

[catpuppy]

“High Heel Sneakers” by Tommy Tucker

https://www.youtube.com/watch?v=8bmbSC9c2ys

[Michael.SF.]

Here's a bit more current one, and suggested by Mrs. Michael.SF:

Short Skirt and Long Jacket -- Cake

[OrioleFan]

Baby Makes Her Blue Jeans Talk - Dr Hook

[Fiji Hill]

Give me a ranch, a big pair of pants, and give me a Stetson, too--and since it's the mid-1930's, give me a prairie moon as well.

Wah Hoo--Bill Boyd's Cowboy Ramblers (1936)

[Grimmy]

!!! Warning!!! ***Hick-Hop***

Knuckles - Cowboy Boots and Shorts

https://www.youtube.com/watch?v=Wpo6TVxg4CY

Safe for work, if you’re ok with your co-workers knowing you listened to this.

[certrtwngnut]

Fairies Wear Boots. Black Sabbath
The Low Spark Of High Heeled Boys. Traffic

[Grimmy]

Josh Gallagher - Boots Like Mine

https://www.youtube.com/watch?v=6bh1E5qBXVw

[spel_grammer_an_punct_polise]

“Are you going to take the man with the raggedy clothes?” HEH!

[Michael.SF.]

Here's one from Elvis, no not that one:

Angels Want to Wear My Red Shoes -- Elvis Costello