The aviator jacket, crewneck sweatshirt and jeans were an ’80s and ’90s uniform for young Hollywood. His long hair put a more rock ‘n’ roll spin on his heartthrob persona. The hiking boots are a granola move that’s hard to relate to.
Chiseled face, bangs, pinstripe suit, high-waisted pants and a bolo tie — what’s not to love? This Tom Cruise era is one of his best, and definitely was the making of a movie star.
Early days, baby-faced Cruise was still finding his fashion footing. The tank top with a blazer is giving off Miami vibes, yet the tight jeans bring it back to West Coast loving.
The silk printed shirt and breezy cropped jacket feel very much from the “Cocktail” era. The legging jeans and suede boots are like “Lord of the Dance”: amusing, but not ideal.
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A big fan of a clip-on bowtie and black studs, the whole look today seems really retro and cute, but he could do so much better. Having Nicole Kidman by your side, though? Perfection.
He’s clearly in his “Mission Impossible” era with the shaved head and leather blazer — not one of his best looks. The black turtleneck paired under the blazer feels uncomfortable — just like how Penélope looks.
The buzz cut works much better here with this relaxed black suit. The pants are a little too flared but the silver tie and white shirt are flattering.
The “Risky Business” era with the vintage T-shirt, ’80s jeans and cropped brown leather biker is equally cool yet innocent. He should consider regrowing the bangs — they’re a vibe.