In a very large group, like a whole middle school or a whole company, try to find a smaller group of people to befriend and be cool with. Situate yourselves as the “in” group in opposition to the lamestream, er, the mainstream. In a smaller group, it might be more appropriate to remain aloof to play it cool. If you come out too strong, you’ll likely just make everyone think you’re a weirdo, not cool. Find another cool buddy to be cool with and position your small clique as the in group.

Practice vague responses to specific questions about your experiences that will seem cool. If someone asks if you’re a virgin, or have ever smoked a cigarette, say, “What is this, a sewing circle?” or “That’s a boring question” and change the subject. Throw it back in their face. Never make stuff up. It won’t make you seem cool to lie and say you’ve been to Europe, or that you’ve done illicit things in the back of a car when you haven’t. The truth will come out eventually and you’ll be exposed and embarrassed.

Play devil’s advocate in group discussions and casual conversations. Don’t get attached to being right or wrong, just poke at people’s expectations and dissent every now and then for the sake of coolness. All your friends ragging on a teacher? Stick up for her. Being different is cool. Alternatively, it may be “cooler” to join up with the crowd in some cases. In middle school, acting cool might mean embracing the newest Justin Bieber song, even if you’re not crazy about Biebs. You can still listen to the good stuff when you’re alone. But try to be true to yourself.

Let other people talk first. Practice good listening skills, staying quiet until someone else wants to start the conversation. Acting cool means you’re not desperate for chat. Just take ’er easy. Whatevs. Take long pauses before you speak, even if you’re fairly sure of what you’re going to say. Dramatic pause will give people the chance to contemplate your smarts and your seriousness. Be stoic, like Kathryn Hepburn, Clint Eastwood, and the titans of cool. Don’t forget to slow your roll, too. Walk more slowly. Look around, scoping the sites. Smell the flowers. Walk with a cool lope, rather than an efficient bustle.

Keep a close watch on your social networking, unfriending or ignoring anyone who hates on your awesomeness. You don’t need to listen to it. Instead, surround yourself with people who’ll lift you up and support you in your coolness. Prepare cool responses to haters. If someone tries to make fun of the super-hip style you’re trying out at school, saying, “What are you wearing?!” have a cool response prepared just in case: “Maybe I should let my mom dress me, like you do. " Spread the coolness around and bestow it on others. The bigger your cool clique, the less chance haters will have of effecting you. Build a strong group of cool friends with similar interests so you won’t have to be a lone wolf.

Seek out a diverse group of friends. Befriend other kids at your school that aren’t necessarily considered “cool” and speak up for them to your friends. Build good will rather than sewing resentment. Some recent studies show that kids considered “cool” in middle and high school end up experiencing functional difficulties in their early adult years, as a result of pretending to have more mature experienced early in life, alienating friends and close ones. [2] X Research source Don’t make the same mistake as the ruthlessly cool. Keep your real friends around.

Paul Newman in Cool Hand Luke. Sometimes nothing is a real cool hand. Work shirts and banjos never looked cooler than on Newman in this classic flick. Study his icy gaze and his witty come-backs as you cultivate your style. Bonus: being familiar with this oldie flick will make you stand out among the Transformers-obsessed. See also: Steve McQueen in Bullitt, Peter Fonda in Easy Rider, and live clips of Johnny Cash. Audrey Hepburn in Breakfast at Tiffany’s. Hepburn’s bootleg brand of glamor made her a style icon in the 60s. Striking sophistication and manic weirdness can go hand-in-hand, she taught us. Also check out Brigitte Bardot in any film, Anna Karina in Band of Outsiders (obscure French film bonus points!), and Nancy Sinatra clips on YouTube. Vintage Fashion photography. Check out Mae West, Betty Page, and issues of Vogue from the mid-50s to the 70s. There’s a whole wealth of cool going unnoticed at the local library. Need a fresh breath of style in your life? Go back to the source.

Some trends like skinny jeans and high-waisted pants may not look great on everyone. It’s not cool if it doesn’t look good. Find something that you like to wear. Wear sunglasses for classic cool. There’s one constant in the cool-fashion universe: sunglasses look awesome on everyone. Get some cool shades, prescription if you wear glasses, and rock them when you’re outside. Keeping them on indoors is lame.

Try not to tap your feet anxiously, or chew your fingernails, even when you’re just sitting. Sit quietly and contemplatively. Anxiety makes everyone anxious. Quiet dignity? That’s cool.

If you like sports, pick one and commit to a team or building a particular skill. Play soccer, football, basketball, golf, tennis, or whatever sport drives you wild with competitive energy. Get as good as you possibly can and get into shape by playing often and working out. If you don’t like traditional ball-and-net sports, many people still cultivate an athletic-coolness by getting into yoga, long-distance running, weightlifting, cycling, or hiking. These are excellent ways to get fit without having to join a team.

Take every opportunity for competition seriously. When Rafael Nadal was injured and recuperating, the loss of tennis competition drove him nuts, so he threw himself completely into competitive high-stakes poker to keep his competitive edge razor-sharp. That’s cool. try to be a good winner and a good loser. Cool means you drive others and yourself to succeed at the highest level, but also realize that you’re ultimately playing a game. If you lose, congratulate your opponent and have the dignity to appreciate their achievement. There’s nothing cool about whining like a sore loser.

Go to public parks and gyms to meet other like-minded cool athletes. Play pick-up games in your area to make sporting friends and feed your competition monster. Be a beast on the field.

Some hot brands for the cool athlete include North Face, Patagonia, Under Armour, Nike, and Adidas. These companies make regular clothes as well as extreme-use gear for a variety of purposes. Pick gear appropriate for your interests. Every sport likewise has a specific range of task-specific stuff you can check out when you learn more about your sport. Team memorabilia and jerseys are also super-common among cool athletes. If you love basketball, get an old Sixers throwback jersey and a ball-cap. Rep your favorite teams.

Pick your favorite teams and rivalries, with extra bonus points for local and regional teams. It doesn’t make any sense to rep the Yankees if you live in Atlanta, unless you can claim some connection to the source. Be authentic to be cool.

Check out cool books, classics like Kerouac’s On the Road, Plath’s “The Bell Jar,” Marquez’s One Hundred Years of Solitude, and more contemporary hip-lit: anything by Tao Lin, Karen Russell, Roberto Bolano, or Haruki Murakami. Check out cool culture magazines like Vice, Bomb,” The Believer, Aesthetica, Oxford American, The Brooklyn Rail, and Interview. Check out cool culture sites, like The Onion, Aquarium Drunkard, Slate, Narrative, and Brooklyn Vegan.

Check out cool archival record labels like Numero Group, Tompkins Square, and Light in the Attic, to learn about old obscurities. While the lame kids go gaga over Mumford and Sons, go deep into Laurel Canyon desert folk, Minneapolis soul comps, and weird ambient music from the 80s. Good and obscure equals cool. Go to local shows and learn about the local scene in your area. If you can get in on the ground level with the next hip band before they get big, you can tell all your friends you knew them back when they were playing in your basement. Cool points +1000. Collect vinyl records, both old and new. CDs are dead, and MP3s lack the cache of a sweet stack of vinyl. Most new records come with download codes anyway, meaning you can still check out the same record on your iPod. Bonus!

Alternatively, if you’re at a party full of “too cool for school” types, who sneer and can’t even be bothered to take off their leather jackets, it might be cooler to speak out. Be the one cracking jokes, cutting up, and being loud. Find the mainstream and act in opposition to it, if you want to act cool.

When you see Ninja Turtles novelty tees at K-Mart, the trend has probably crossed over into lame. When you hear a band in a diamond commercial, they’re probably not super-hip anymore. Move onto the next thing when it’s reached it’s pop culture apex. No shame.

Frequent trendy coffee shops to meet bohemian sorts in your area. Carry a hip book with you and dress in your coolest clothes. Hit up art openings, concerts, and poetry readings. You’ll attract the other cool sorts. At your school, see if there’s an art, guitar, or foreign language club you could join to hang out with other cool and worldly people. It’s a good way to make cool friends. If your school doesn’t have a music appreciation society, start one.

Maybe you could carry a cane with a rattlesnake on the handle for no reason. Maybe you develop a love of exotic butterflies, and decorate your room with your collection of specimens. The line between weirdo eccentricities and “cool” is sometimes blurry. Have fun with it and do something you really enjoy that’s odd, unique, and cool. Try thinking of calling cards, cool quirks that’ll make you different and cool. Even things as simple as ordering bloody mary at night, or deciding to never see Forrest Gump might qualify as “cool. " Be the never-seen-a-single-episode-of-Seinfeld guy? Why not?

Jeans and shirts should not be ironed, but not super-wrinkly or dirty. Holes in your jeans are cool, and so are paint-splattered boots and sneakers, as if you just came straight form the studio. Necklaces, bracelets, and piercings are usually cool, if they make you feel good. Use your judgment. Shark teeth necklaces look cool on Johnny Depp, but might make you look like a dork. Combined with other cool stylings, you can start to build a look for yourself. Wash your hair the night before school, rather than right before school. Going to bed with slightly-damp hair can give you rockstar body and frizz, giving it a controlled kind of wildness. You can always comb it out if it looks too crazy. Cool make-up is usually minimalist. Go for a light natural look, highlighting your features and your own natural coloring.

Smart-cool people are always plugged in, have always seen that meme three days before it showed up on your newsfeed, and always have opinions about the newer, the more efficient, and the most innovative dispatches from the tech world. The newest Facebook privacy updates? Smart-cool people read about that three days ago, thank you very much. Always try to update your hardware as soon as possible. The newest start-up apps, devices, games, and trends are usually cooler than slightly dated varieties. The new iPhone is cooler than the old iPhone. Why are you reading a paperback? Get an e-reader, already. You want to be the guy with the newest roll-out, drawing envious stares on the train during your commute.

You don’t necessarily have to be super-plugged-in to stay on top of innovative consumer trends. Even within your own neighborhood, you can seek out new restaurants, always going somewhere else, finding the next best thing. Be restless and keep moving.

Online friends are real friends. Forge relationships and friendships with people online, who’ll get your particular brand of humor, your interests, and your personality. If you spend a considerable amount of time in your own head, online communities can be very welcoming. It might feel like home.

Develop a thirst for knowledge of all sorts, not just what you’re interested in or consider your speciality. If you want to be a hacker, be the hacker who can quote Macbeth at length. If you want to be a novelist, learn how to do things with your hands, in addition to all that brain-work. You know there’s nothing cool about blowing off your homework, even when the supposedly “cool” kids at your school seem to blow it off all the time. Find confidence in the knowledge that you’ll be in college, surrounded by awesome, intelligent, and beautiful people, while these fake cool kids go nowhere.

Novelty t-shirts are the calling card of the smart-cool. Shop online for funny shirts with inside jokes you and your friends will get, that will leave the lame jocks scratching their heads. Found a Monty Python tee you dig? Cool.