For years, Matt Damon's attitude toward style was thus: "Fuck you." Things have changed somewhat. The 41-year-old Oscar owner still doesn't dress to be the main attraction, but he has found his style in the form of unfussy minimalist threads. Along with his Good Will Hunting-fueled Cinderella ascent came a swarm of preppy golf course get-ups, super-sized fits and even a nasty bout of mom jeans. Damon's more concerned about impressing you with his work, which if you haven't noticed has been pretty consistent and virtually free of post-Oscar blunders—from reputable ensemble pieces (Ocean's Eleven, The Departed) to the blockbuster Bourne trilogy. Here, we follow the Contagion star's road from frat-boy frugal to suited-up linchpin.
Phase I: The Legend of Baggy Vance
At 22, Matt Damon may look graduation-day fresh, but no. He's just flipped higher learning the bird, dropping out of Harvard a year earlier only a few credits shy. He goes onto much better things—pretending to be a student in the 1950s dude-centric prep school drama School Ties.
Damon is still drowning in both anonymity and fabric in the form of massive Charlie Chaplin trousers with no crotch in sight. The size of his pants is inversely proportional to the amount of care he takes.
Phase II: A Burgeoning Caterpillar
Life is good. Good enough to splurge on a leather jacket from Wilsons. Good Will Hunting, the first screenplay Matt and BFF Ben Affleck ever wrote, has hearts aflutter. Their bromance is reaching PDA-level heights. Matt's solid choice of a slimmer-fitting V-neck sweater reveals the seeds of a future leading man.
Damon arrives to the 70th Annual Academy Awards with his mom, donning a respectable three-piece tux. He leaves with an Oscar for Best Original Screenplay and Hollywood's false acceptance. His happiness is contagious and Champagne-fueled.
Matt has spent the past four years avoiding the Cuba Gooding Jr./Snow Dogs route to obscurity by choosing roles wisely—Saving Private Ryan, The Talented Mr. Ripley, Ocean's Eleven. His style remains a mix of safe neutral suits and Chuck E. Cheese chic. Feels like something's missing here.
Phase III: A Star Is Bourne
A perfectly snug tee. The outline of what looks like a cell phone in his pocket. These clothes fit! Funny what a box office smash and a hot chick (now his wife, Luciana) can do. All roads lead to Matt's crowning achievement this year as People's Sexiest Man Alive. Sort of better than an Oscar.
Of note: During this time, Affleck, fresh off Daredevil and Gigli, has grown a beard of regret and loathing masked under a b-boy stance.
The mom jeans have spoken, and Matt's Red Sox allegiance causes a momentary relapse into shapeless boyhood clothing bliss.
Phase IV: A Style Assassin (Killing It in a Good Way)
It's taken two Ocean's sequels and countless George Clooney advice sessions for Damon to invest in a slender ensemble worthy of the term "dashing," not to mention a tie that pops.
If you were drinking a beverage, you probably just did a spit-take. Matt Damon is wearing colors. The style gods shed confused tears of joy.
While Affleck is back to starring in grade-A films, Damon's grown comfy in his role as one of Tinseltown's leading men. Black-on-black is apt. Bespoke suit. Spit-shined shoes. He's evolved. But something tells us his eff-you attitude is hiding in there somewhere.