1. Post-grad white guy who traipses around Southeast Asia for a few weeks/months, drinking heavily and doing copious amounts of drugs, all in a well-documented mission to “find himself.”
You Will Need: Ray Ban sunglasses, striped t-shirts/wifebeaters, enough money for weed and not too much else, a smartphone, and a gaggle of women you hope to impress with tales of your cultured escapades. A camera that was at least as expensive as the initial plane ticket, used to take extreme close-up shots of plants and food and blurry, drunken ones of the adorable locals you meet while out at night. A blog to document everything, with a very ~interesting~ title, such as Le Flâneur Professional.
2. Aspiring ingenue whose questionable talent will not get in the way of her dreams of ~making it big~ on Broadway (or, more likely, as an extra on Girls).
You Will Need: Elaborate period costume, to be photographed in “artsy,” heavily-filtered images and plastered all over social media. Stage makeup and an updo sprayed within an inch of its life. An evening-long monologue about the new project you’re working on in either New York or LA, and how awesome it is and these celebrities who are peripherally involved — celebrities you got to meet, of course.
3. Brooklyn transplant who has just moved, doesn’t understand the real estate market, and is about to get screwed on rent.
You Will Need: Spritely, hopeful, quirky clothes that do not yet reflect the degree to which your bank account is about to be ravaged into a wheezing corpse of its former self. Think things that show how excited you finally are to be in a city that gets you, such as a zesty scarf that your boring suburban hometown wouldn’t understand.
4. Intern who is just entering the work force and has no clue how to dress professionally, aside from TV shows and stock photos of middle-age guys pointing at Power Point presentations.
You Will Need: An ill-fitting, drably-patterned button-down shirt that is by no means attractive, but meets a minimum standard of “professionalism.” To be paired with polyester slacks or a demure skirt, depending on preference. Should be appropriate enough to use in for your LinkedIn photo, and could also double as Facebook profile picture, if you are literally the most boring person in the world.
5. The cool guy whose existence seems only confirmed by frequent photos of him appearing on social media, taken by professional party photographers at nightclubs and promotional events.
You Will Need: Leather jacket, t-shirts that somehow function as both acceptable party wear and the kind of thing that doesn’t look too overdone, sunglasses that you may leave on indoors for a large portion of the evening. A girl who, despite your vague-at-best familiarity with her, is always at arm’s reach for a photo-op. A cup that is permanently half-full of vodka Red bull. Snapbacks, so many snapbacks. Strong command of the word “bro.”
6. Aspiring writer who spends the most of their spare time in an off-the-beaten-path coffee shop (one they may actually work at, in their not-spare time), typing away as they draw inspiration from every incredibly interesting passerby.
You Will Need: A moderately quirky outfit that represents simultaneously your differences from the 9-5 crowd and your somber intellectualism. (You are an artist, but still a writer, after all. You’re not trying to be the craziest-looking person in the coffee shop, only the most interesting.) A coffee and a muffin, only to be purchased once because you cannot afford to continue purchasing things as you spend more time there. What are you, made of money?
7. Party girl who never quite knows when things are over, but is always down to egg everyone on to do another round of shots, chastising them if they choose to go home early instead.
You Will Need: An outfit you don’t care about spilling rum and Coke down the front of, a complete lack of awareness about everyone’s collective need to slow down at least slightly after college, a Deer Park bottle full of vodkain your party. Remember to punctuate conversations with loud screams about how awesome things are, offers to drive if anyone needs/wants to go anywhere, and constant, pointed inquiries as to who has cocaine (followed by a “Just kidding!”).
8. Person whose objective in life is clearly to get photographed by a street fashion photographer at some point, otherwise why would they be wearing some of these outfits?
You Will Need: An absurd outfit that makes absolutely zero sense in the realm of actual people who have to go to work every day. Options include: a tutu, heels over 5 inches, haircuts that are shaved on one side, bolo ties, bespoke suits worn with insane sneakers, head-to-toe denim, grandma sweaters worn with evening gowns. To be worn with a look that says, “Yeah, it’s 3 p.m. on a Wednesday afternoon and I have nowhere better to be than at this café giving everyone the stink eye. I am better than you.”
9. Morning-after mess who is far, far past the point of caring what anyone else thinks about how they look.
You Will Need: As depicted in the photo, a fedora and Uggs. Whatever clothes happened to be laying around on the floor. A strong will to fall over and die, if only so the inside of your skull would stop screaming at you.
10. Girl who just moved into her new place and has both Photobooth and Tumblr, and who wants to share this immense joy with her followers.
You Will Need: Pajamas — but the classy ones that you want Tumblr to think you sleep in all the time. A glass of alcohol (preferably wine) to hold up impishly as you click ~30 photos of yourself, only to pick the most flattering one to post with a self-deprecating comment along the lines of “Ugh, so tired.” The alcohol is to show that you know how to have a good time, the comment that you’re not conceited.