Green’s Dictionary of Slang

(UK und.) said of one who is unable to get started on a project or raise necessary funds.

1935

Thieves Slang ms list from District Police Training Centre, Ryton-on-Dunsmore, Warwicks 2: Can’t get his boots on: Cannot get a start or cannot raise his train fare.

(US black) to be sophisticated, aware; thus boot-wearer, an aware individual.

1941		D. Burley N.Y. Amsterdam Star-News 15 Nov. 14: Joe Q. Hipp was a solid cat; has his boots on, laced up snug.
1941		D. Burley N.Y. Amsterdam Star-News 15 Nov. 14: He was no Lane [...] He was an old boot wearer with cowhide laces.

(US black/campus) to have sexual intercourse with; thus abbr. n. use boots, sexual intercourse (see cit. 1989); boot-knocking, sexual intercourse (see cit. 1999).

1986		Salt-N-Pepa ‘Tramp’ 🎵 You ain’t gettin paid, you ain’t knockin boots.
1987		Boogie Down Productions ‘Super Hoe’ 🎵 Yo, Kris. I really knocked the boots on those two big-butt females last night.
1989		Ice-T ‘You Played Yourself’ 🎵 But you fool out, your pockets got blew out / And after the date, no boots, you got threw out.
1999		Hip-Hop Connection Dec. 45: Knocking Boots. To have sex [...] it derives from the motion of a man’s hips hitting the woman’s ass, which produces a slapping sound. The motion literally knocks her boots (buttocks).
1999		Guardian G2 4 Aug. 17: Jerry Falwell, former leader of the Moral Majority [...] was less relaxed about all this same-sex boot-knocking.
2000		Snoop Dogg ‘Set It Off’ 🎵 Yo’ lady think I’m cute, I be knockin her boots.
2007		‘Skepta’ ‘Single’ 🎵 Before you knock boots / Make sure you put on your hat / With your birthday suit.
2008		A. Wheatle Dirty South 126: I still found it hard to believe that Noel and Priscilla had ever knocked the boots.
2012		G. Johnstone ‘No Through Road’ in Crime Factory: Hard Labour [ebook] Your ex-wife is knocking boots with a gawky finance twat.
2019		C.D. Rosales Word Is Bone [ebook] June and Kiddy were in there, but [they] couldn’t hear his knocking for all the knocking boots of their own.