The life of Tony Bennett in pictures

Like his singing voice, Tony Bennett’s personal style was flexible, direct, and self-assured.

He resisted the temptation to change his approach to music when rock overtook the pop charts, shied away largely from the many clothing trends that came and went during his seven decades in show business, and wisely stuck to smartly tailored tuxedos and suits, many from Italian fashion brand Brioni. For more casual moments, he wore slacks and a jacket, sometimes with a dark turtleneck instead of a dress shirt and tie.

Ironically, by sticking to a style that has allowed itself to be felt when it comes to both music and fashion, Mr. Bennett has managed to avoid the trap of being strongly attached to any era.

In recent decades, when men’s fashion magazines celebrated the ring-a-ding-ding style of the 1950s and early 1960s with retro-looking outfits, they tended to focus on Frank Sinatra, Dean Martin, and the other dyed-in-the-wool members of the Rat Pack.

And as other singers of Mr. Bennett’s generation became subjects of retro chic, he was still playing in theatres, nightclubs and award shows with a new crop of stars including Stevie Wonder, KD Lange, Elvis Costello, Red Hot Chili Peppers, Bono, Sting, Celine Dion, John Legend, Amy Winehouse and Lady Gaga.

“The only thing that lasts is the quality—the suits, the music, the people,” Bennett said in a 2010 interview. “It’s all the same. My suits are expensive but they never age, and I can keep them for up to two decades.”