Sep. 2006

September 2006: At the International Film Festival of San Sebastian in wraparound sunglasses that were quite popular in the mid-oughts (and continue to be favored by law enforcement officials). 

Nov. 1991

November 1991: At Isaac Mizrahi's New York Fashion Week show with Naomi Campbell and a polka dotted shirt. 

Feb. 1990

February 1990: At the Cinema Paradiso premiere, looking like a slick airport traveler. 

Jan. 1985

Mid-'80s school boy charm. 

Superteen Magazine shoot, 1980

Some three years before finding fame in The Outsiders, Dillon was shot in the L.A. living room of photographer Brad Elterman for Superteen Magazine. As the photog recalls after running into the actor at a bar 15 years later, "He did not have a clue who I was, nor did he care."  

June 1980

June 1980: Open shirted and fancy free at a Kids are People Too party with Brooke Shields (bonus points: check out Brook's loose braid).  

Nov. 1983

Paint. Splattered. Jeans. 

July 1996

During his Cameron Diaz years, Dillon took to a tropical, Miami Beach look. 

July 1998

Chest hair for days at the There's Something About Mary L.A. premiere in July '98. 

Nov. 1981

Feb. 1991

Catwalking. 

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