Frank Sinatra stepping out of a helicopter with a drink:

 

A man ice skating in a suit (1937):

 

The definition of old school cool. Cary Grant in the 1950s:

 

Clint Eastwood with actresses Olive Sturgess and Dani Crayne in San Francisco, 1954:

 

A couple dancing in a 1950's "Be Bop" theater as everyone looks on:

 

A young Harrison Ford:

 

 

A couple on Michigan Avenue in Chicago (1975):

 

A young boy stealing the show, back when middle school kids knew how to dance (1950):

 

Children of Chicago (1941):

 

A gang of greasers in NYC, 1950:

 

A young Kevin Spacey (1980s):

 

 

High school fashion feature in Life Magazine (1969):

 

Dean Martin & Angie Dickinson on the set of Rio Bravo, 1959:

 

Marlon Brando's screen test in "Rebel Without A Cause" (1955):

 

A young Michael Caine in 1959:

 

Caroline Kennedy walks ahead while her father, the most powerful man in the world, carries her doll. (1960):

 

An old family photo from the early 1900s:

 

The Beatles before they were famous:

 

Cosmos host and astrophysicist Neil DeGrasse Tyson at a college wrestling match:

 

Three boys pose for a camera on the streets of Jamaica:

 

A young Sean Connery relaxing on the couch:

 

Paul McCartney and Mick Jagger sit opposite each other on a train to Bangor. (1967):

 

Sigourney Weaver in a suit:

 

Ernest Hemingway's striking passport photo (1923):

 

Diana Rigg (Olenna Tyrell from Game of Thrones) in 1967:

 

Canadian Prime Minister Pierre Trudeau and his cabinet - 1968. These men knew how to wear a suit:

 

Brigitte Bardot visits Pablo Picasso at his studio near Cannes in 1956:

 

Audrey Hepburn at a premiere on September 14, 1953:

 

Jimi Hendrix backstage at Monterey Pop Festival, 1967:

 

Sophia Loren, one of the only actresses to win an Oscar, Grammy, and Golden Globe awards:

 

6 time Golden Globe winner Paul Newman boating in Venice during a film festival (1963):

 

A businessman doubling as a graffiti artist:

 

David Bowie's mugshot:

 

Elspeth Beard, shortly after becoming first Englishwoman to circumnavigate the world by motorcycle. The journey took 3 years and covered 48,000 miles:

 

How they used to date in the 1950s:

 

Girl on a scooter (1969):

 

The gorgeous necklines of the 1950s:

 

Leather clad English rocker girl:

 

Women boxing on a roof in LA (1933):

 

Muhammad Ali looking dapper: