Shedding his flannel, Dean cleans up really well! From 7.12 "Time after Time" (#ThankyouRobbie!)
Dean's expression might not be the best but the tux certainly deserves an honorable mention! From "Red Sky at Morning" 3.04.
Take your pick: light reflecting in his eyes, full cowboy look; or lurking in the shadows sideways glance! Either way, Dean's western cosplay in "Frontierland" 6.18 is mysterious and engaging! Ride-em, cowboy!
Can you resist a man in uniform? Dean puts your resolve to the test in "Pac-Man Fever" 8.20.
No collection of Dean's best looks would be complete without his perfectly fitted undercover suit, tie and overcoat. This shot frames Dean beautifully, as is befitting the episode - "Regarding Dean" 12.11.
(Lest we stray too far into the shallow end of the pool, your assignment, should you decide to accept it, is to find a gif from 8.08 "Hunteri Heroici" when Dean walks away from the camera to go over to talk to Castiel. It provides ample testimony of the perfect fit of Dean's suit!)
Michael!Dean's impressive, confident presence in cap and multi-layered proper attire is cinematically framed in a mesmerizing shot, with the long, empty alley of light as a backdrop. From "Stranger in a Strange Land" 14.01.
Returning to the halo effect depicting the theme of angels' impact on Dean, Michael!Dean shows off his Heavenly perfection in "Gods and Monsters" 14.02. The distinction between Dean and Michael is so evident in this intimidating presence!
A white tux, top hat and tap shoes? We saved the best for last! From 15.10 "The Heroes' Journey."
The Smiles and the Tears
Dean is known for shedding One Perfect Tear. His grief and pain couldn't (shouldn't) be classified as "breathtaking" but the moment before that tear drops, Dean's anguish grips the heart. This series of shots are some of the most breathtakingly emotional profiles of Dean.
2.22 "What Is and What Should Never Be"
3.01 "The Magnificent Seven"
7.04 "Defending Your Life"
6.20 The Man Who Would Be King"
Thankfully, Dean recognizes the need to balance the tears with some fun. In his all too few lighter moments, Dean's face betrays the impish mischief that is always there, under the surface. Looking into the camera, you can't help but love Dean's "I got you, with a smile" assurance. From "Live Free and Twihard" 6.04.
We all love it when Dean laughs out loud, whether it be at Sam in glitter or The Three Stooges' slapstick, but this "Yellow Fever" 4.06 post-episode special clip is Jensen's (as Dean) embarrassed yet proud, "That was fun!" smile. Priceless.
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