Green’s Dictionary of Slang

1. a thug.

1888		Richmond River Herald (NSW) 23 Nov. 4/2: The Judge recognised [...] that he was not a New York ‘toughy’ and inquired where he lived. The prisoner told a very plausible story about being the son of a respectable merchant.
1940		R. Chandler Farewell, My Lovely (1949) 156: So I yelled and a toughie in a white coat came in and showed me a blackjack.
1958		(con. late 19C) D. Burley N.Y. Amsterdam News 15 Feb. 13: A five-foot six-incher, who [...] bucked the Irish toughies .
1968		J. Hersey Algiers Motel Incident 154: He was always the toughie.
1971		J. Mandelkau Buttons 120: I had innumerable hot dog riders and biker toughies visiting me with intentions of joining up.
1989		M. Dibdin Tryst (2003) 29: Jimmy, a plump toughie with curly fair hair.
2004		T. Winton ‘Boner McPharlin’s Moll’ in Turning (2005) 262: He was a toughie from the abbatoir.

2. (Aus.) a physically and/or emotional hardy individual.

1898		Broad Arrow Standard (WA) 5 Jan. 4/1: ‘Get unto your bunks, you lubbers [...] [M]y name’s Toughie (he was prouder of that than his real name), and I’m the ringer of any shed I care to go into between Burke and Bendigo’.
1906		Sun. Times (Perth) 21 Oct. 4/7: My oath, I’m a regular toughie / And accustomed to shuddering and shocks.

3. (US) an attractive young woman.

1921

Dos Passos Three Soldiers 15: She was a toughie, lived in our street, I used to write mash notes to.

4. one who enjoys playing very ‘rough’ sports.

1929		Phila. Inquirer 16 June n.p.: The ‘toughie’ is the halfback who carries the ball over the goal line with a minute to play, the man to lean on when the riot call is turned in.
1968		J. Hersey Algiers Motel Incident 154: He was always the toughie.

5. (also toughy) a ‘hard’, ruthless, callous person.

1932		P.G. Cressey Taxi-Dance Hall 103: Now ‘Toughy’, as I call him, comes from South Chicago. He’s a bad boy.
1939		W. Winchell On Broadway 26 June [synd. col.] The toughies from the press fell in love with the Austrian refugees.
1949		Wodehouse Mating Season 208: The local toughies quiring the potboy.
1956		J. Thompson ‘The Flaw in the System’ in Fireworks (1988) 135: So maybe he’s a toughie [...] We’ve got collectors – boys that know how to make the tough ones soft.
1958		C. Lee diary 22 Mar. in Eight Bells & Top Masts (2001) 95: The Mate was always considered a toughie. Had to be, otherwise too many would take advantage.
1965		W. Dick Bunch of Ratbags 102: Most times the class ‘toughies’ ran the class, not the teachers.
1971		M. Novotny Kings Road 78: He does everything possible to pretend he is a ‘toughie.’.
1981		E. Bunker Little Boy Blue (1995) 145: Where you’re going there’s lots of toughies.
2000		Indep. on Sun. Real Life 23 Jan. 3: TV’s favourite toughie with a heart.

6. (also toughy) something that one finds ‘tough’ to do, understand, accept etc.

1935		F. Wead Ceiling Zero Act II: I didn’t swap with Tex just to hand him a toughy.
1944		J. Archibald ‘It Could Only Happen to Willie’ in Popular Detective Apr. 🌐 He was killing time filling in [...] a toughie [i.e. a crossword puzzle] he had cut out of a morning paper.
1967–8		Baker et al. CUSS 213: Toughie Difficult course.
1986		J. Ellroy Silent Terror 160: ‘It's either going to be an open-and-shut case, or a toughie’.
1996		P. Beatty White Boy Shuffle 48: This one’s a toughie. How many dimples on a golf ball?
1996		J. Byrell Lairs, Urgers & Coat-Tuggers 269: ‘That’s a toughie,’ said Jumpin’ Jerry with corrugated brows.