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1.
A catchphrase and internet rage comic character used to convey elegance, wealth and class. It is associated with Victorian styles like wearing a top hat, monocle or various types of mustaches.

Often used to make something seem classier.
A Classier way of "Like a Boss"
My glasses are broken and i don't have any tape. Oh wait (uses broken glasses side as a monocle)
Like a Sir
by SEKTOR July 25, 2012
 
2.
A phrase used to express the sophistication of one's character. If one wears a monocle or top hat, they most definitely are like a sir. A much fancier substitute for "like a boss".
1. Bro, I totally banged that chick while wearing a monocle. Like a sir!

2. Aristocrat 1: I do say, that performance by GaGa was riveting!
Aristocrat 2: Like a sir!
by CSirness May 29, 2012