"how the clothes one wore could help one's sense of well being, or self esteem. Also how drab or uniform type clothing can be designed to stifle that."

There may well be more songs to suggest that uniforms enhance "one's sense of well being, or self esteem." The "Rout for the Blues" is such a one:
"They're as gallant young fellows as ever you'll see,
Though you search bonny Britain all through.
When dressed in His Majesty's suit you'll agree
There's none can compare with the Blues."

There's a nice verse in "Richard of Taunton Dean" where he dresses up to go courting:
"Young Herchard put on his Sunday clo'es,
his buckskin britches and silken hose,
A brand new hat upon his head As were bedecked with ribbon so red." Whether or not his wooing was successful depends on the version you prefer.