“Tough tomato” described a tough boxer (“one tough hombre” is now used) by as early as 1922. Jack Conway of Variety had described club fighters (with more heart than physical skills or technique) as “tomato cans” by 1921.
 
“Tomato” was also 1920s slang for an attractive woman. A “tough tomato” was a feisty woman, such as the characters that actress Bette Davis frequently played. This use of “tough tomato’ is cited in print from at least 1955, but could date to the 1930s.
 
The alliterative phrase ‘Tough tomatoes!” means the same as ‘Tough luck!” and “Tough titty!” and “Tough shit!” and “Too bad!”—the speaker realizes that other people don’t like an outcome. “Tough tomatoes!” is cited in print from 1928 and is still used.
 
       
5 July 1922, New Castle (PA) News, “Forkins Defeats Ralph Schappert: Forkins Performs Like Champion Against Tough Hard Coal Miner” by Bart Richards, pg. 20, col. 2:
But here’s the funny part folks. He couldn’t hurt this tough tomato from Wilkes-Barre.
 
Google Books
Rejections of 1927
Garden City, NY: Doubleday, Doran and Company
1928
Pg. 295:
“That’s tough tomatoes,” I replied courteously, remembering there was a lady present who could probably understand military cuss words even if she couldn’t…
   
31 August 1937, Abilene (TX) Reporter-News, “Not Same Louis Says Schmeling” by Bill Boni, pg. 2, col. 2:
At the time, even though Tommy Farr, the tough tomato from Tony-Pandy, was cuffing the fuseless Brown Bomber up against the ropes, it seemed a rash statement.
 
6 February 1939, Daily Kennebec Journal (Augusta, ME), “Speaking of Sports” by Richard G. Kendall, pg. 2, col. 7:
He dodged, rolled, and clinched to avoid the sweeping shots of the very tough tomato from Texas.
     
Google News Archive
7 January 1944, Eugene (OR) Register-Guard, “Red, A Juvenile, Looks At The Eugene Curfew Law” by Wesley Gates, pg. 1, col. 6:
You are either in it or you are not, and to use some slang, it is just “tough tomatoes” all through school if you’re not in the clique.
     
20 February 1955, Los Angeles (CA) Times, “A Writer Refutes a Critic” by Cecil Smith, pg. D1:
“If,” said the reviewer, “this blond dame did write this book, they are some tough tomatoes in California.”
     
11 August 1964, Delaware County Daily Times (Chester, PA), “Helen Help Us” by Helen Bottel, pg. 9, col. 2:
“Bad berries”—What “tough tomatoes” used to be.
(Slang list by “California Teen”—ed.)
 
6 October 1967, Oakland (CA) Tribune, “Stage and Screen” by Gerald Nachman, pg. 59, col. 1:
The book is divided into the following sections: “Tough Tomatoes” (Ona Munson, Cleo Moore, Gloria Dickson); “Other Women”...“Society Ladies”...and “Sweet Motherly Types”...
 
Google Books
Cinema Booklist
By George Rehrauer
Metuchen, NJ: Scarecrow Press
1972
Pg. 392:
The faces are placed in categories based on the roles usually portrayed, such as “tough tomatoes,” “society ladies,” “bad guys,” “clean old men,” etc.
   
Google Books
Blue italian
By Rita Ciresi
Hopewell, NJ: Ecco Press
1996
Pg. 81:
“And they also say first come, first served — and if you don’t like it, tough tomatoes.”
   
Google Books
The Charles Dickens Murders
By Edith Skom
New York, NY: Delacorte Press
1998
Pg. 76:
“Tough tomatoes,” said Jill. “That’s what they get for coming in late.”
   
Google Books
In the Whale
By J. C. Greenburg
New York, NY: Random House
2003
Pg. 32:
“Tough tomatoes!” she said. “Does that mean we’ll have to go back into the whale’s mouth?”
   
Google Books
The Many Lives of Marilyn Monroe
By Sarah Bartlett Churchwell
New York, NY: Metropolitan Books/Henry Holt
2005
Pg. 334:
She (Marilyn Monroe—ed.) became a tough, tough tomato. A tough tomato. She became a tyrant as a producer, a big tycoon trying to lay the law down to the Hollywood bigshots.
   
Google Books
Unlimited Grace:
The Power of Christ Within
By James A. Kirkwood
Xulon Press
2006
Pg. 182:
If we don’t like this, tough tomatoes!