Green’s Dictionary of Slang

squire n.

[SE squire, a title orig. used to denote an esquire, a young man of good birth, attendant upon a knight, but by 17C referring mainly to a country gentleman]

1. [17C] a fool [one who is foolish enough to serve another].

2. [17C–1900s] a general title used ironically in a number of contexts, e.g. apple squire under apple n.1 ; see also phrs. below.

3. [early 19C+] a general term of address, no particular rank or intimacy indicated.

4. [mid-19C] (UK Und.) a successful criminal.

5. [mid-19C] (US) a magistrate.

In derivatives

squirish (adj.)

[late 18C–early 19C] foolish.

In phrases

squire of Alsatia (n.) [Alsatia n.; best known as the title of Thomas Shadwell’s play, first staged in 1688]

1. [late 17C] a gentleman who has been drawn to the criminal world and there found himself fleeced, robbed and generally rendered destitute by its denizens.

2. [late 17C] an overly generous man.

3. [late 17C–early 19C] a rich fool.

squire of the body (n.) [mocking the SE esquire or the ‘country squire’ + SE body; cf. knight of the... n. and its combs]

[17C–early 18C] a pimp, or a term of abuse.

squire of the company (n.)

[late 18C] one who treats the rest of the company.

squire of the cross (n.) [cross n.1 (1)]

[mid-19C] (UK Und.) a thief.

squire of the gimlet (n.) [SE gimlet, used as a corkscrew]

[late 17C–late 18C] a publican, a tapster.

squire of the pad (n.) [pad n.1 (1)]

[early 18C] a highwayman.

squire of the petticoat (n.) (also petticoat-peer, petticoat squire) [metonymic use of SE petticoat = women]

[late 17C] a pimp; as a term of abuse.

squire of the placket (n.) [placket n.]

[17C] a pimp.

stand squire (v.)

[late 18C–early 19C] to treat the company.