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The first rule of hip, much like the first rule of sexy, is never ever uttering the word. But for the sake of conversation, we’re about to dabble in the elusive three-letter descriptor in order to divulge a few shortcuts we’ve gleaned from our tireless study of effortless cool. (Note: tireless studying does not equal you-know-what). So how to look hip, without looking utterly desperate? Here's our own personal bag of tricks:

Get Skinny: Relax. We’re not about to go down the “nothing tastes as good as skinny feels” road. We’re talking about the cut of your clothes: Skinny jeans. Skinny ties. Skinny-cut shirts. You yourself need not waste away, so long as one item of your clothing is ever so slightly malnourished.

Think Big: Yes, we know we just got through telling you that “less is more” but as slight as
your slim-cut tank/toothpick jeans/shrunken blazer may be, that’s how oversized your wide-leg jeans/boatneck tee/belted boyfriend button-down should go.

Keep it in the Family: Shopping in vintage clothing stores is cool, shopping in your parents’ archived Summer of Love-wear and grandparents’ Great Gatsby gear is cooler. The key is to hone in on one item of clothing, and incorporate it into your daily look; taking a blanket approach could result in appearing costumey, like you’re going to one of those Gossip Girl masquerade balls those kids always seem to be throwing. Note: A good rule of thumb is to target the things Mom and co. wore when they were your age. Although, it should be noted, that grandpa’s high-waist chinos are very now.

One Love: Hipsters have a well-documented love affair with the unbalanced—we’re talking fashion here, but we could name more than a few cult heroes that fit said mental descriptor too. Whether it’s a one-sleeved dress, a lone dangling earring or a renegade stripe in your hair, one is the magic number.

Micro Manage: Lest you appear to be a fashion victim, the hippest way to approach a trend is by hinting at it, as if your entire outfit is the unsuspecting guest of honor at a surprise party being thrown by your Ikat nails/Navajo topsiders/reverse fish tail braid. The more off-kilter your chosen trend is, the more straight arrow the rest of your look should be.

Rock A Classic: As mentioned above, nostalgic sartorial and on-trend styling play a huge role
in hipster fashion, but timeless pieces are the glue that holds it all together: The Mackintosh Trench Coat, the perfect white tee, the little black dress, the penny loafers, the aviator sunglasses—these are the blocks that hip is built on.

Line Up: Stripes are hipster catnip. Seriously, they can’t get enough of them. The most surefire incarnation is a Breton. Works every time.

Go to Extremes: Playing with scale can yield giant fashion dividends in the accessories realm. Whether it’s a so-teensy-you-need-a-magnifying-glass-to-see-it pendant or a baseball-size cocktail ring, the key is to accessorize as if you went shopping in Gulliver’s Travels (either in tiny people populated Lilliput or giant dominated Brobdingnag). Oh, and don’t ever mention Gulliver’s Travels.

Get Personal: You’ll notice that hipsters are big on embellishment: a personalized pin here, a strategic rip there—the effect should look homemade and one-of-a-kind, like no one else will ever be able to replicate it. But be warned, renegade alterations can prove addictive. So before you take scissors to that new pair of jeans, stop and ask yourself: What would Chloë Sevigny do?

Pack Your Bag: Whether it’s ornate bangles from India or a Liberty print scarf from London, if it’s from far away, it’s worth bonus points. If it’s limited edition and from Japan, you’re that much closer to being friends with Spike Jonze.