Old School Cool: Some of the Greatest Photos Ever Taken
There’s something truly special about “old-school cool,” a style and charisma that seems to transcend the ages. Different eras have their own unique version of what it means to be cool, whether it’s the rebellious spirit of the 1980s punk movement or the elegance of 1880s fashionistas.
A man and his beloved pet duck that he raised from an egg, 1994.
Let’s take a delightful journey back in time to explore the fascinating photos that encapsulate the spirit and style of yesteryears.
The term “cool” has been associated with various cultural trends and personalities over the years. The 1960s, for instance, saw the rise of the rock and roll era, with iconic figures like The Beatles leading the charge in both music and style. Their relaxed, yet trendsetting look became the gold standard for cool, influencing generations to come.
A young Phil Collins in the 1960s.Willie Nelson in 1960Jayne Mansfield, 1960Burt Lancaster and Audrey Hepburn in The Unforgiven, 1960.Ingrid Bergman and her daughter Isabella Rossellini, 1960s.Vivien Leigh and Lauren Bacall at a party celebrating the opening night of Duel of Angels on Broadway, 1960.Kirk Douglas, Jean Simmons, and Tony Curtis between scenes in Spartacus, 1960.Jimi Hendrix getting his hair done. 1960’sDolly Parton, live late ’60’sJayne Mansfield and Mariska Hargitay, 1960s Dolly Parton, 1960s.The Three Stooges visiting Yellowstone in 1969.Audrey Hepburn in Breakfast at Tiffany’s (1961).
In contrast, the 1970s was an era defined by disco and glamorous styles. This was the time when fashion was bold and expressive, with vibrant colors and flared trousers making a statement. Celebrities like John Travolta in “Saturday Night Fever” epitomized disco fever, bringing dance moves and shiny suits into mainstream consciousness.
Dolly Parton, 1970sA 17-year-old’s yearbook photo, 1970s.A hippie teenager in the 70s Marlène Jobert, French actress and the mother of Eva Green, 1970s Jodie Foster rides a skateboard in Paris, 1970s.Jane Seymour, c.1970sMarlon Brando and photographer Mary Ellen Mark, 1970s Enjoying cocktails in the 1970s.Helen Mirren, 1970sSally Fields, 1970sCatherine O’Hara, 1970s Ladies of the 70sJack Nicholson and Barbra Streisand during an Academy Awards party in 1970.Michelle Phillips and Dennis Hopper’s during their 8-day marriage in 1970Frank Zappa with his parents, 1970Lars Ulrich with his father, Tennis pro Torben Ulrich. Mid 1970sA young Slash with his parents, 1970A woman and dogs spotted in Los Angeles, 1970.Elizabeth Taylor and Richard Burton at the 1970 Academy Awards.Uncle and Nephew playing poker, c. 1978.Mark Hamill and Annie Potts on the set of Corvette Summer, 1978.Heading to a concert in 1977.Awesome frog Halloween costume, 1977.Vincent Price, Carrie Fisher, Ringo Starr and John Ritter, 1978.Sean Penn’s yearbook photo, 1975.Model Jenny Claire and her mini, 1972. Arnold Schwarzenegger, Hugh Hefner, and Wilt Chamberlain at the Playboy Mansion, 1977. Robert Plant backstage with The Runaways, 1975. Photo by Barry Schultz.Original frontman of AC/DC Bon Scott in 1979Barack Obama with a group of friends called the “Choom Gang” in 1979. Chi Chi Rodriguez and his cool caddie John Lynch at the 1975 masters.Lynda Carter representing Arizona at the Miss World USA 1972 Fifth Avenue, NYC, 1972.Cybill Shepherd, 1972Anthony Bourdain at his High School Graduation, New Jersey, 1974Michael and Shakira Caine, 1973 A woman cuts her birthday cake in Iran, 1973David Bowie, 1975Johnny Cash eating cake in a bush, 1971.English singer, songwriter Kate Bush, 1978Joan Jett, 1977Sid Vicious, Baton Rouge 1978 Keith Richards in Seattle airport on the 1972 Stones tour of the USAOzzy Osbourne, 1976David Gilmour, Pink Floyd. Live At Pompeii 1971.Stevie Nicks working on Rumours, 1976Robert Redford and Barbra Streisand in ‘The Way We Were,’ 1973.Alma Reville with the prop head of her husband, Alfred Hitchcock, 1972.Christopher Lloyd (Banquo) and Christopher Walken (Macbeth) in the stage production Macbeth at Lincoln Center, New York, 1974 Andre the Giant holding up NFL quarterback Joe Theismann, 1975Linda Blair with Black Sabbath, 1976.Elton John at home with his collection of shoes, 1975.Crosby, Stills, Nash & Young, 1974. Photo by Joel Bernstein.Mick Jagger and his bride Bianca at their wedding in 1971, Keith Richards in the background John Belushi, Muddy Waters, Johnny Winter, and Dan Aykroyd. 1977Punk Rock girl London, 1979The Clash & The Undertones photographed together in 1979Robert Redford attends the premiere of All the President’s Men, in which he plays the legendary journalist Bob Woodward, in Washington, D.C. in 1976.Robert Redford with journalist Bob Woodward on their way to the book party for All The President’s Men in June 1974.
Let’s not forget the 1980s, a time marked by neon colors, shoulder pads, and big hair. It was a decade where confidence and extravagance were celebrated, reflected in both personal styles and the era’s music scenes. Punk rockers, with their edgy and daring aesthetic, challenged the norms and embodied a new form of rebellious cool.
Epic 80s momentsKurt Cobain with his girlfriend Tracey, 1980’s Sting, the wrestler, reading a Far Side book, 1980s Freddie Mercury and Michael Jackson, early 1980s,First day in school for Mila Kunis, 1980’s.Michael Jackson, 1980sTina Weymouth – the bassist of Talking Heads, 80s.The Cure on Columbus Avenue, 1980Susan Kare, famous Apple artist who designed many of the fonts, icons, and images for Apple, NeXT, Microsoft, and IBM. (1980s)Diana Ross finishing up a Rib, 1980. Photographed by Ruven AfanadorThe damned in New York, 1980’sBurlington Mayor Bernie Sanders picks up trash on his own in a public park after being elected in 1981.John Cassavetes and Gena Rowlands, August 1982.Jennifer Lopez at her a birthday party in New York, 1999Dennis and Randy Quaid, 1982 Rowan Atkinson and Christian Bale, 1984. Sarah Jessica Parker, Rob Lowe, and Robert Downey Jr. at the Governors Ball, 1988. Prince stands victorious over Charlie Murphy during a game of basketball, 1985. Larry Nance at the inaugural NBA Slam Dunk Contest – 1984 Sigourney Weaver and Mel Gibson pose for a photo in 1982 Mister Rogers throws the opening pitch at a 1988 Pittsburg Pirates game Kate Capshaw, Harrison Ford and Ke Huy Quan during the filming of Indiana Jones and the Temple of Doom in 1984 Mrs. Fields, the founder of the Mrs. Fields cookie company, 1982.Ric Flair meets a 12-year-old Dwayne Johnson c. 1984 Cameron Diaz cheerleading in high school, 1989.Bam Margera riding his first skateboard, 1988. Tom Cruise and Rebecca De Mornay, 1983.Bruce Springsteen, Michael Jackson and Billy Joel, 1985 Jerry Seinfeld and Larry David, 1989 Nicolas Cage and his father, August Coppola, 1988Stephen King opens the gates to his new Victorian-style house, guarded by bats. November 1982 Joaquin Phoenix and River Phoenix, with their parents and siblings, Summer,Liberty & Rain at home in LA California circa 1983Sting giving his autograph to a young Gwen Stefani, 1983 Winona Ryder, Jodie Foster and Julia Roberts in 1989Molly Ringwald, 1985.Drew Barrymore at 9 lighting Stephen King’s cigarette, 1984Arnold Schwarzenegger and Grace Jones on the set of ‘Conan the Destroyer,’ 1984Valerie Bertinelli and Eddie Van Halen getting married in 1981David Lee Roth and his signature leap circa 1982Mike Tyson playing Punch Out, NES • 1987Kurt photographed by his sister, Kim Cobain, Aberdeen, WA, September, 1986Ozzy Osbourne, dressed as a ’50s housewife, ironing his daughter Aimee, 1984Robert De Niro and Meryl Streep in Falling in Love, 1984Princess Diana look-alike contest in Washington D.C., 1985Siouxsie Sioux, 1983‘The Half Suit’ Photo and concept by Pippa Garner, 1982Zitkala Sa, Sioux Indian and activist, c. 1898.The line to see Goonies on opening day at the Liberty Theatre in Astoria, Oregon way back in 1985.A young Elizabeth/Liz Hurley at the Batcave in London, 1984.Jon Voight brings his children, Angelina Jolie and James Haven to the Oscars, 1988.Tom Cruise, Matt Dillon, Patrick Swayze, Ralph Macchio, Emilio Estevez, C. Thomas Howell, and Rob Lowe on the set of “The Outsiders,” 1983.Robert Redford and Meryl Streep in ‘Out of Africa’ (1985).
Going further back, the classic styles of the 1940s and 1950s continue to have a lasting impact. This was an era where elegance and simplicity were key, with Hollywood stars like Audrey Hepburn and James Dean symbolizing sophistication and effortless charm. Their influence on fashion remains relevant, proving that true style never really goes out of fashion.
The Undertaker poses with an older woman, c. 1990sPhil Collins in the 1990s.Carrie Fisher feeds Meryl Streep chocolate cake, 1991Heath Ledger’s Polaroid selfie with Larisa Oleynik, Joseph Gordon-Levitt and Julia Stiles on the set of 10 Things I Hate About You, 1999. Hippie dad walking with his daughter. Amsterdam,1968Johnny Depp and Salma Hayek at a party, Hollywood, 1995.Princess Grace of Monaco visiting JFK at the White House, 1961.Ryan Dunn and Bam Margera in their High School yearbook, 1990s. Jim Carrey and Cameron Diaz and their stunt doubles on the set of The Mask, 1994Britney Spears and Melissa Joan Hart on the set of the (You Drive Me) Crazy music video, 1999. Queen Elizabeth with her mother in the 1990s Fisher Stevens and Michelle Pfeiffer, 1992. Brittany Murphy, 1998. Sharon Tate at the premiere of Rosemary’s Baby, 1968. Sophia Loren and Jayne Mansfield, 1957.Senior Picture, 1990.The Storyville Jazz Club in Copenhagen, Denmark, 1952Chris Farley and his dad in the 1990s Judy Garland with her baby Liza Minelli, c. 1945. Woman at the beach in 1910.The cast of Pulp Fiction, 1994.Nirvana at a party just before they became famous. Dan Cortese, Jon Stewart. and George Clooney at MTV’s Rock & Jock Baseball, 1994.Gary Oldman and Demi Moore, 1995Linda Ronstadt, 1969 Debbie Reynolds with a Stanley cup, 1951 Skateboarding in Uvalde, Texas, 1965.The ice man delivering a 25 pound block of ice, 1928.A same high party in 1997.Christian Bale at his 18th birthday party, 1992A wedding in 1949.My Mom on her wedding day in November, 1951Albert Einstein at the Beach, 1939.7 year-old George Clooney, 1968 Penelope Cruz and Salma Hayek, 1990s. Britney Spears in Tokyo, 1999Sandra Bullock, 1990sRose Byrne and Heath Ledger, 1999Anita Ekberg, 1950sBetty White in 1948The Beatles waiting to cross Abbey Road, 1969Jimi Hendrix aged 15, with his first electric guitar14-year-old Sigourney Weaver attends a Beatles concert at the Hollywood Bowl, 1964Shakira, 1990.Danny DeVito at Oratory Preparatory School, Summit, NJ, 1961 John Wayne on Vacation in Acapulco, 1959. Photo by Phil SternKeanu Reeves, 1990sActor Sean Connery reading while doing push-ups, 1957. Jane Russell drawing Marilyn Monroe behind the scenes of Gentlemen Prefer Blondes, in 1953.Pictures of Buddy Holly and his fans taken backstage, 1959. The first selection of the Miss Slender Legs competition, Miami, 1952. Photographer Ansel Adams, 1950Marilyn Monroe with Lassie, 1950s. Harry Belafonte and Dorothy Dandridge, 1950sMarilyn Monroe and Arthur Miller on their wedding day, 1956A woman is ticketed for wearing a bikini, 1957.The employee cafeteria at Disneyland, 1961.Peter Dinklage in high school.Sean Connery, 23. Prince, 17. Young FDR Jr. in 1937 at age 23.A young woman photographed in the 1910s.A cowboy, 1890s.3 young women eat spaghetti on inflatable mattresses, 1939.Two ladies ride in an early car model, 1900.A cool girl posing with her car around 1920.This mirror portrait was taken 100 years ago in Japan.New car in South Richmond, Virginia, 1938.Taking a break while building the Chrysler Building, New York, 1930.A Victorian Girl from the 1860s!A stylish family outing in 1946.Robert Downey jr at the academy awards 1993Hedy Lamarr photographed by Alfred Eisentaedt, 1938 Jayne Mansfield, 1950sGrace Kelly, 1950s“How’s your leg?” Grace Kelly’s entrance scene in “Rear Window”-1954Lauren Bacall and Marilyn Monroe at the premiere of “How to Marry a Millionaire,” 1953 Marilyn Monroe and Sammy Davis Jr. publicity photographs for “How to Marry a Millionaire,” 1953. Lana Turner, Judy Garland, and Hedy Lamarr on the set of Ziegfeld Girl, 1941. Marilyn Monroe photographed by Bruno Bernard at Racquet Club Resort Hotel in Palm Springs, 1949.Elizabeth Taylor on the set of Giant, November 1956 Audrey Hepburn hanging out with Dean Martin and Jerry Lewis at Paramount Studios, 1953Marilyn Monroe in cat-eye glasses, 1950s.Barbara Stanwyck, 1920s
The journey through time reveals that “cool” is not just about fashion—it’s about attitude and authenticity. Each era brought its unique flair and mindset, making the pursuit of cool a constantly evolving story. By looking at these photos, we can appreciate the diversity and creativity of past trends, reminding us of the timeless yet ever-changing nature of style.
Lana Turner – “The Postman Always Rings Twice” 1946Hedy Lamarr, 1940sLauren Bacall, Humphrey Bogart and Marilyn Monroe-1953 Oscars by Michael Ochs Archives Judy Garland with her baby Liza Minelli, 1947Lucille Ball, 1940sClara Bow, 1927A young Agatha Christie.Gillian Anderson, 1990’sCameron Diaz and Jim Carrey at Cannes Festival, 1994Fans watching the 1992 MLB All-Star Game in San DiegoA Teenager At An Elvis Presley Concert At The Philadelphia Arena 1957 Jimi Hendrix and The Who at the Monterey Pop Festival, 1967One of the first pictures taken of Black Sabbath, 1968.Alice Cooper drinking a beer with Colonel SandersSister Rosetta Tharpe: The Godmother of Rock & Roll.Bob Marley, Mick Jagger and Peter ToshLouis Armstrong plays for his wife, Lucille, in front of the Sphinx and Great pyramids in Giza, Egypt, 1961Waylon Jennings and Johnny CashLes Paul and Paul McCartney Muhammad Ali and The Beatles, 1964Candice Bergen photographed by Milton Greene, 1966.Dustin Hoffman and Jon Voight in Midnight Cowboy, 1969.In 1956, Marilyn Monroe poses for photographers as she boards an American Airlines plane from New York.Seventeen-year-old Elizabeth Taylor washing her golden cocker spaniel.Vivien Leigh in a publicity photo for Waterloo Bridge, 1940.Joséphine Baker, France, 1920Vivian Leigh in ‘Caesar and Cleopatra,’ 1945.Joanne Woodward and Paul Newman in Paris during the filming of Paris Blues, 1961.Dean Martin, Kirk Douglas, Jimmy Durante, and Tony Curtis at a Friars Club event, in the late 1950s.Publicity photo of Carole Lombard, 1935.Joan Fontaine and Laurence Olivier in Rebecca, 1940.Paul Newman in Cool Hand Luke, 1967.Kim Novak and James Stewart in Vertigo, 1958.Ingrid Bergman and her daughter Isabella Rossellini.Elizabeth Taylor c. 1951.Audrey Hepburn in My Fair Lady, 1964.Janet Leigh and Tony Curtis at home with their daughters, Jamie Lee and Kelly in 1959.Jacqueline Kennedy and Princess Grace Kelly of Monaco, 1966.Lauren Bacall, Humphrey Bogart, and Katharine Hepburn arriving in London after the filming of “The African Queen”Gregory Peck and Brock Peters in To Kill a Mockingbird, 1962.Jessica Tandy, 1949Don Johnson and Melanie GriffithVivien Leigh behind the scenes of Gone with the Wind, 1939.Grace Kelly, c. 1955.Katharine Hepburn on the set of The Philadelphia Story in 1940.Janet Leigh, 1950s.Audrey Hepburn, Rex Harrison, and director George Cukor, My Fair Lady, 1964.Marilyn Monroe, 1950s.Susan Hayward “I Want to Live!” Best Actress Oscar, 1958.
These glimpses into the past also highlight how cultural icons have shaped what we consider cool. Their influence reaches beyond clothing and hairstyles; they have impacted attitudes and lifestyles. As we celebrate these legendary photographs, we remember the icons who defined their times, leaving an indelible mark on history.
Joanne Woodward and Paul Newman dancing at an after-party celebrating her Oscar win for “Three Faces of Eve,” 1958.Elizabeth Taylor with her Oscar for Best Actress in “Butterfield 8” at the Academy Awards, 1961.Elizabeth Taylor smiles while walking with her second husband, British actor Michael Wilding, at the Academy Awards in 1954.Teenage Elvis with his cousin Harold in 1953.Steve McQueen at Paramount Studios Gym, 1962, by William Claxton.Vivien Leigh pictured with her mother, Gertrude Hartley, circa 1922.Doris Day at the Aquarium, jazz club on Seventh Avenue.Sophia Loren Holding the chin of her sister, Maria.Katharine Hepburn with her sisters Marion and Margaret, 1939.After traveling for work, Josephine Baker greets three of her children at the airport in 1954.Vivien Leigh, seen here at the Oscars ceremony in 1940 with Laurence Olivier.Leonardo DiCaprio, Johnny Depp, and Brad Pitt.John Wayne, with his son, on location in Mexico for the filming of “The War Wagon.”The first meeting of Grace Kelly and Prince Rainier III of Monaco, 1955.Marilyn Monroe surrounded by fan mail, 1955. Photo by Slim Aarons.Dana Andrews & Teresa Wright in The Best Years of Our Lives – 1946.Liberace and Elvis Presley jam backstage at a night club in 1956.Elizabeth Taylor and daughter Liza Todd, c. 1950s.Sophia Loren on the set of Yesterday, Today and Tomorrow, 1963.Marilyn Monroe and Mickey Rooney at the premiere of ‘The Emperor Waltz’, 1948.Shirley MacLaine with her brother, Warren Beatty in 1942.1934 dance marathon participants at Crystal Lake Park in Marion, Ohio.Liberace being seen off to France by a fan in the 1950s.Elvis Presley and Cissy Houston (Whitney Houston’s mother), 1969Michael Caine at home with his mother, Ellen (1964)Axl Rose sits handcuffed in the back of a police car after he was arrested at Kennedy Airport upon his return from a European concert tour, 1991. Photo by Bill Turnbull. Joni Mitchell playing guitar for Eric Clapton and David Crosby, 1968Young men smoking, drinking, and playing cards Stetson University dorm room, Florida, ca 1900. Janis Joplin pouring herself a drink before going on stage at Woodstock, 1969Lunch at the Universal studio commissary, 1963.Marilyn’s last photo taken by George Barris, 1962A champagne inspector wearing a special mask to protect against accidental discharges, c. 1933.24 Year-Old Orson Welles outside CBS’s Columbia Square studios at 6121 Sunset Boulevard on his first day in Hollywood, August 1939A cop poses with some Flappers, Los Angeles, California, 1920sMiss Idaho Potato, 1935Alan Rickman, Hugh Laurie, Kate Winslet, Harriet Walter and Emma Thomson- 1994Edward VIII wearing Japanese garb while on a tour of Japan as Prince of Whales in 1922The Who drummer Keith Moon playing pinball, sometime before September 1968William Shatner and Leonard Nimoy Taking a Lunch Break On the Star Trek SetChange of swimsuit on the beach. 1930sGeorge Harrison photographed by Paul McCartney whilst on a hitchhiking trip to Wales in 1959.John Lennon dancing with Louise Harrison, mother of George Harrison, at the Dorchester Hotel after the film premiere of, “A Hard Days Night” at the London Pavilion on July 1964.Brian May, 1963A vintage selfie from 1934Karl Malden and Marlon Brando on the set of One-Eyed Jacks, 1961.Cary Grant and Alfred Hitchcock on the set of North by Northwest, 1959.Audrey Hepburn wears the costume for her Broadway debut in the play Gigi written by Colette and Anita Loos, photographed in 1952. Photo by Norman Parkinson.Grace Kelly at the 8th Cannes Film Festival in 1955.Audrey Hepburn in Roman Holiday (1953). Color by Klimbim.Sophia Loren in Scandal in Sorrento, 1955.Clint Eastwood at home circa 1961.Grace Kelly on the set of To Catch a Thief, 1955.Janet Leigh, 1954.Elizabeth Taylor with her Siamese cat (1956). Photo by Sanford Roth.Tom Ewell and Marilyn Monroe in The Seven Year Itch, 1955.Frank Sinatra and his wife Nancy listening to music in their home in 1943.Mel Ferrer and Audrey Hepburn in War and Peace, 1956Audrey Hepburn greeting Barbra Streisand after watching her performance in Broadway’s Funny Girl at the Winter Garden Theatre in 1964.Audrey Hepburn arrives at London Airport in 1953.
Reflecting on “old-school cool,” we see a rich tapestry of style evolution that speaks volumes about the social and cultural contexts of each era. It’s a testimony to human creativity and the desire to express individualism. So as we reminisce through these incredible photos, we embrace the nostalgia and enduring charm of coolness from the past.
Whether you’re revisiting the past or discovering these styles for the first time, there’s always something to appreciate. These remarkable images not only capture moments in time but also remind us of the dynamic nature of self-expression throughout history. Enjoy the journey through these timeless treasures!
Clint Eastwood, washing his car, North Hollywood, Calif., (1958) Photo by John R. Hamilton.Joanne Woodward and Paul Newman, 1958.Johnny Carson at 15 (1940).Jane Fonda, younger brother Peter, father Henry Fonda, and his third wife Susan holding their daughter Amy.Bette Davis, 1930.Marilyn Monroe and Dale Robertson at a charity baseball game, 1952.Paul Newman and Sophia Loren photo shoot for Lady L, 1965.Dean Martin, Jerry Lewis, and Marilyn Monroe (1953).Paul Newman and Elizabeth Taylor in Cat on a Hot Tin Roof, 1958.Lucille Ball in 1935.Hattie McDaniel and Vivien Leigh in Gone with the Wind (1939).Grace Kelly relaxing with family and friends aboard the Constitution. April, 1956.Grace Kelly with her mother, Margaret, and sister, Lizanne, 1954.Rita Hayworth standing on a yacht in a scene from Lady From Shanghai, 1947.A young Elizabeth Taylor with a cat.Elizabeth Taylor with her mother.Joanne Woodward and Paul Newman relaxing at home.Audrey Hepburn and Humphrey Bogart on the set of ‘Sabrina’ (1954).Marilyn Monroe and Arthur Miller.Sophia Loren and son Carlo Ponti Jr. at home, photographed by Alfred Eisenstaedt, 1969.Olivia de Havilland by George Hurrell, 1938.Bette Davis and her mother at the premiere of ‘All About Eve’ at Grauman’s Chinese Theater (1950).Laurence Olivier and Vivien Leigh.Cary Grant and Marilyn Monroe on the set of Monkey Business (1952).Elizabeth Taylor and Montgomery Clift in ‘A Place in the Sun’ (1951). Bette Davis on vacation in Hawaii after filming The Letter, 1940.Rita Hayworth cooking at home, c. 1942.
