baldfaced shirt, n. — Green’s Dictionary of Slang

baldfaced shirt n.

also baldface

[SE baldfaced cattle, Herefords, which have white faces; the bald element, pointing up the lack of pattern, may be the root of the boiled shirt, another term for a dress shirt, although such starched, formal shirts were literally boiled to achieve the rigid front]

(US) a dress shirt with a starched front.

1883		W.E. Curtis Summer Scamper 65: A cowboy who had been East for a visit and came back wearing ‘a short-horn collar and a bald-faced shirt’.
1889		Farmer Americanisms 33/2: Bald-faced shirt The name by which a Western cowboy knows a white shirt. It is thought to come from the fact of Hereford cattle having white faces.
1908		E. Bronson Reminiscences of a Ranchman 277: A di’mond big as a engin’ head-light staked out in th’ middle of his bald-faced shirt.
1912		W. Beggs Rhymes from Rangeland 173: So I got up a full dress suit to gratify my passion, / And got a low-necked, bald-faced shirt to be up with the fashion.
1922		P.A. Rollins Cowboy 108: The shirt [...] always was collarless and starchless (not ‘boiled,’ ‘biled,’ or ‘bald-faced’).
1936		R.F. Adams Cowboy Lingo 38: A stiff shirt was ‘bald-faced,’ ‘boiled,’ or a ‘fried’ one.
1944		R.F. Adams Western Words (1968) 11/2: baldface A cowboy’s word for a stiff bosomed shirt, sometimes called boiled.
1954		M. Frink Cow Country Cavalcade 230: He was anxious not to be taken for a cowboy, so he outfitted himself with a bald-faced shirt and a hard hat.