Hipsters are nothing new to Western civilization. People have been rocking ironic-artsy-retro chic since ancient Rome.
For example, Polykleitos' Doryphoros (spear-bearer), which art historians consider to be the first representation of a hipster in Western art history.
Note his trendy aviator shades and his organic canvas messenger tote (with enough room for his sketchbooks AND his Lucky Strikes!).
Fun fact: The Converse sneakers were commonly used by Greeks in midnight vintage-bicycle raids on neighboring towns.
Next, Robert Campin's Portrait of a Woman.
The bored expression, the nose piercing, the souvenir headdress picked up at the latest indie show, and the Parliment cigarette dangling from her lips; Campin uses subtle clues to allude to this Flemish woman's hipster-ness.
Now, in this statue of Renaissance artist Leone Alberti, we see that he clutches a Deerhoof/Sicbay split LP in his right hand. He is a part of the most unbearably prickish branch of hipsters, commonly referred to as a "music snob".
Moving into the Baroque period, we find Caravaggio's Supper at Emmaus.
It's quite a detailed piece but notice the subtle placement of Pabst Blue Ribbon beer cans in the hands of Jesus and Luke. Also note the ironic hunting hat of the man on the left.
And finally, looking at Waterhouse's Romantic piece, The Lady of Shallott, notice the Village Voice clutched in the girl's right hand. Staring ahead in a cool blase way, concerned with locating a vintage Linn Sondek LP12 record player, she nearly drops the alternative weekly into the water! Ah haha ha ha! Art humor FANTASTIC!
There you have it, guys. All hail the immortal hipster!