Green’s Dictionary of Slang

1. (US) a personally tailored garment.

1899		Ade Fables in Sl. (1902) 38: She [...] put on her Tailor-Made, and the Hat that made her Face seem longer.
1902		Ade Girl Proposition 105: How much did your Tailor-Made set you back?
1967		(con. 1940s) M. Dibner Admiral (1968) 253: Fumbling with the many-buttoned opening of his Navy tailor-mades.

2. (usu. prison, also tailor job) a factory-produced cigarette.

1903		Muscatine Jrnl (IA) 20 Jan. 11/4: Ready made ‘coffin nails’ or what are better known by cigarette fiends as ‘tailor-made’.
1911		St Louis Post-Despatch (MO) 6 Mar. 10/7: A fine of not more than $10 for any boy caught smoking a cigarette, whether ‘rolled’ or ‘tailor-made’.
1926		(con. 1918) L. Nason Chevrons 27: He and Darcy took the proferred cigarettes, tailor-mades, too.
1937		E. Anderson Thieves Like Us (1999) 85: Old Red wouldn’t smoke nothing but tailor-mades.
1947–53		W. Guthrie Seeds of Man (1995) 296: Ya woodn’ part with one of them tailor jobs, woodja?
1948		J.E. Webb Four Steps to the Wall 54: If you’re caught with tailor-mades you get thirty days added to your time.
1957		D. Niland Call Me When the Cross Turns Over (1958) 68: Sorry I got no tailor-mades.
1967		M. Braly On the Yard (2002) 342: Cat produced a pack of tailor-mades from his shirt pocket.
1978		R. Caron Go-Boy! 16: Go ahead, man. Take one. This is going to be your last chance for a tailor-made.
1981		P. Barton Bastards I Have Known 28: Cigarettes were a pretty valuable commodity [...] we traded the much sought-after tailor-mades.
1985		B. Robinson Aussie Bull 2: My father turned me green with a big cigar as an intended lesson, but I soon found out that his hidden ‘tailor-mades’ were better.
1996		(con. 1946) G. Pelecanos Big Blowdown (1999) 84: He lighted a tailor-made and dropped the match in the neck of the bottle.
2002		J. Lerner You Got Nothing Coming 62: If these youngsters don’t P.C. up like punk-ass bitches, they can pay, say, a carton of tailor-mades a month.
2004		L. Redhead Peepshow [ebook] I lit a tailor-made [...] It was great to be smoking again.
2018		T. Pluck ‘Hot Rod Heart’ in Life During Wartime 104: ‘Mmm, never smoked a tailorr-made before’’.