50 Best Dressed Characters On TV And Some Of Their Best Looks

40 of 49

Photo: The CW

Chuck Bass – Gossip Girl

It’s funny how a well-tailored suit can make you forget about how awful a man is. Chuck Bass was a real jerk in the first few seasons of Gossip Girl, but he was so charming and enthralling, it seems to make the ladies forget all about his past sins.

While I’m not a giant fan of a man under 50 wearing an ascot, I’m willing to forgive it on Chuck Bass. The embodiment of Upper East Side wealth and class, Chuck didn’t leave his house without looking aristocratic and stately.

He and Blair made quite the WASPy couple, and you could smell the money from across the room. Every pocket square, silk tie, and leather belt were meticulously chosen by Chuck to promote his image of undoubted confidence. Even in that silly high school uniform, you knew he knew he looked good.

On another man, this could read as being both gross and presumptuous, but Chuck wore his ego like a badge of honor. No matter what he actually had on, he looked marvelous. Sure, he was swarthy and a little greasy sometimes, but his suit game was unlike any other for a man of his age.