Green’s Dictionary of Slang

Dick’s hatband n.

[the orig. hatband was a narrow strip of material wrapped around the hat, esp. as a badge of mourning. The identity of Dick is not known – ‘some local character or half-wit’ (OED) – but his hatband was presumably an improvised and absurd object; however, Brewer, Dict. of Phrase and Fable (1894), suggests Dick = Richard Cromwell (1626–1712) and hatband = a crown, which as a republican he could not wear]

1. (US) anything makeshift; thus I wouldn’t know him from Dick’s hatband.

[US]Bartlett Dict. Americanisms 114: dick’s hatband. This very singular expression I have often heard in Rhode Island. Mr. Hartshorne calls it ‘one of those phrases which set philologists and antiquarians at defiance.’ It is in general use throughout Shropshire, where it is applied as a comparison for what is obstinate and perverse. Ex. ‘As curst as Dick’s hatband, which will come nineteen times round and wont tie at last;’ ‘As contrary as Dick’s hatband;’ ‘As false as Dick’s hatband;’ ‘As cruikit as Dick’s hatband;’ ‘As twisted as Dick’s hatband;’ ‘All across, like Dick’s hatband;’ ‘As queer as Dick’s hatband.’.
[US]Newberry Herald & News (SC) 7 Jan. 4/1: As cross as Dick’s hatband.
[UK]Eve. Teleg. (Dundee) 24 June 6/2: As cross as Dick’s hatband.
[US]A. Anderson ‘Big Boy’ in Lover Man 51: He [...] always dressed sharper’n Dick’s hatband in a brown wide-striped suit.
[US]G. Wolff Duke of Deception (1990) 183: It was as dark as Dick’s hatband in there.

2. used in a variety of absurd comparatives.

[US]Sun (NY) 6 May 8/1: Mr Maxwell, I understand, had simples tastes—’ ‘As plain as Dick’s hatband’.
[US]Ocala Banner (FL) 12 Nov. 6/2: Why, to any fair-minded person the reason is [...] as plain as Dick’s hatband.
[US]Wash. Herald (DC) 14 Feb. 6/1: It likewise is true that it gets hotter than Dick’s hatband in the summer.

In phrases

odd as Dick’s hatband (adj.)

very eccentric .

[US]St Cloud Jrnl (MN) 27 Oct. 5/1: ‘What made him do queer things all his life?’ I answered, ‘He was always odd as Dick’s hatband’.
[US]New Ulm Wkly Rev. (MN) 12 Aug. 6/1: Cranky, that’s all. She always was as odd as Dick’s hatband.
[US]Phillipsburg Herald (KS) 21 Dec. 3/6: We allus remarked [...] that sech folks was ‘as odd as Dick’s hatband’.
[US]in DARE II 63/2: (Someone who has odd or peculiar ideas or notions) [...] Odd as Dick’s hatband.
square as Dick’s hatband (adj.)

misshapen.

[UK]Burnley Exp. 10 June 14/2: Old Lancashire sayings [...] ‘As square as Dick’s hatband’.
tight as Dick’s hatband (adj.)

1. very tight.

[US]Memphis Daily Appeal (TN) 21 Sept. 3/2: A few more jerks of the weather machine and big Muddy will freeze as tight as Dick’s hatband.
[US]Memphis Daily Appeal (TN) 28 Nov. 3/4: The near approach of the Froze-as-tight-as-Dick’s-hat-band season.
[US]Semi-Weekly Interior Jrnl (Stanford, KY) 15 Nov. 1/4: She made an effort to remove it, but it was as tight as Dick’s hatband and growing tighter.
[US]Houston Daily Post (TX) 20 June 4/4: Instead of keeping every place of amusement and refreshment open at all times [...] they close everything up tighter than Dick’s hatband at 12 o’clock sharp.
[US]Interior Jrnl (Stanford, KY) 1 Dec. 3/2: The banks were closed yesterday as tight as Dick’s hatband.
[US]Bryan Daily Eagle & Pilot (TX) 20 Aug. 2/2: How would this plan do — stop the shipment of every commodity [...] to England, and bottle her up as tight as Dick’s hatband.
[US]Hartford Herald (KY) 5 Feb. 4/2: The flu ban is on tighter than Dick’s hatband until April.

2. very drunk.

[US]Columbia Herald (TN) 6 May 1/2: I seed Iky drunk once and that done me [...] Iky Peabody would be as tight as Dick’s hatband before we got back.

3. very efficient, very well done.

[UK]Western Morn. News 9 July 3/4: Good job done, tight as Dick’s hatband.

4. very mean.

[US]in DARE II 63/2: (Nickname for a stingy person) [...] Tight as Dick’s hatband.