The term "hipster style" can seem like an oxymoron. People who follow this fashion trend to the letter can seem as if they have no fashion sense whatsoever, wearing clothing that is ill-fitting in clashing colors and patterns. The hipster style, however, does have some fundamental rules its adherents follow, and it is rooted in a historical movement many people still relate to.
The term "hipster" was first used in the 1940s and 1950s, describing a group of youths who admired jazz musicians and beat poets. These hipsters wore dark, tight clothing with the occasional burst of color. Think of Audrey Hepburn in "Funny Face," as she dances about the smoke-filled nightclub. The term was picked back up in the 1990s to describe a different generation that was also interested in alternative music and literature. Instead of forging a new style, however, these hipsters chose to emulate the previous hipster generation. They borrowed the berets, the baggy sweaters, the thick-rimmed glasses and the black color palette of the first hipsters and interjected a good dose of irony.
Hipster style now leans heavily on vintage clothing. Sweaters that were last worn by elderly people, preferably in too-tight sizes, are ideal. Vintage dresses are also a popular choice, as long as they're worn over leggings of a contrasting color. Jeans are worn tight, with no flare at the ankle. Flannel shirts have also been taken into the hipster style palette, although they must be worn loose and in multiple layers for the proper look. Tee shirts that are tight and contain images of retro products, no longer available, make suitable additions to a flannel outfit. Casual shoes include Doc Martens, preferably beat-up pairs that have long seen better days, and Converse sneakers with a thick layer of dirt. Formal shoes should be vintage wedges, with high, thick soles.