Note: This first appeared on the now-defunct comedy website, Nearly Robots in 2012.
“The Little Rascal”: The Little Rascal is one of the most confusing hipster boy fashions of the moment. It’s the easiest of the styles to spot because it is a grown man who is dressed like a seven year-old. His attire is characterized by either being comically too big or too small for him. The Little Rascal look is as follows: he is wearing a flat brim, elasticized baseball cap from the 80s that was meant for the head of a toddler. His glasses are at least three times too big for his face as is his loose oversized t-shirt, the sleeves of which are parachute-esque in relation to his tiny arms. His pants are of course a fraction of a size away from just being painted on and are for some reason cuffed at the ankle. He may or may not be wearing suspenders, but you can be sure that they are serving no functional purpose as it would take the vacuuming force of the universe’s deepest black hole to make his pants fall down. If you’re unsure whether or not you’ve encountered a Little Rascal Hipster Boy, imagine placing a paddleball or a bag of marbles in his hand. If the image fits, you’re in business. The Little Rascal Hipster Boy has not had sex from exactly the beginning of the period of time that he began dressing like the Little Rascal Hipster Boy because no sound-minded woman would have sex with someone who looked like a seven year-old.
The “My Girlfriend Shops at Vintage Stores”: This is the hipster boy who looks good. …A little too good. His style appears effortless. Things are matching, but not matching too much; he’s wearing the appropriate colours and styles for the season; the materials and fabrics are of good quality; his clothes are clean and without holes. Girls are checking him out left and right, but he can do nothing about it because he was dressed this morning, like a Ken doll, by his obsessive, albeit extremely stylish girlfriend.
“Fat Beard Cowboy”: This is exactly what it sounds like. You’ve got yourself a chubby man who has taken it upon himself to bring forth unto the world a beardo of seismic proportions. Thus, already looking as though he has been lost in the woods for weeks, he compliments his rustic features with a plaid shirt, pants that just plain do not fit, and some kind of fancy shoe that ends up looking like a cowboy boot in the context of the rest of the outfit. Show him you appreciate the effort by telling him to, “Broke-Back Dat Ass Up!”
The “Prop Personality”: This is the type of hipster boy whose style is largely determined by a series of props he runs through as he tires from one to the next. He may go through a period where he smokes a pipe all the time and compliments the pipe with a tweed blazer and leather elbow patches. He may go through a period where he decides to drink out of a leather water bag and pairs it accordingly with a vaguely native American headband. He can be talked into any prop as long as it is either vintage or from a minority community. This means you could persuade him to carry around an old vacuum while dressing like a Hasidic Jew.
“Hip Hop Hipster”: This is pretty simple. Flat-brimmed baseball caps, hoodies, and tight pants in colours and patterns that you didn’t even know existed. And a lot of crazy huge jewellery, like things your bubby would wear. Type in “Cool Kids” on Google image search for reference. Also, thanks to Pharrell, Spongebob Squarepants is prominently featured in this look for reasons that someone is probably already writing their thesis on.