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Miansai Bracelets

Miansai by Michael Saiger has been around for a while, but that doesn't make the label any less cool. The fish-hook on these guys adds a little bit of unexpected charm. Plus, they're not gender specific.

Eames Book

The too-cool-for-school sibling often prides himself on his refined aesthetic. Anyone with an appreciation for design would welcome a book all about one of the industry's most celebrated duos, Charles & Ray Eames.

Cannibis Candle

Okay, I know what you're thinking, but hear me out. On a recent trip to see Sarah Mills, the woman who cuts my hair (and my too-cool-for-school brother's hair at my suggestion) I caught the wiff of this candle. And no, it doesn't smell like a bunch of hippies smoking ganja, it smells more like an old library. It's the most distinguished smelling candle I've ever smelled.       

Air Quote Mittens

Cool people love correcting people and using air-quotes. Mittens have always presented a problem for cool kids because the classic two-finger air quote turns into an odd hand-flapping motion. These mittens solve everything.

Geneva Lab Speakers

If you're feeling very generous, these speakers are the perfect option for your absurdly hip sib. They're well designed, hook up to an iPod and have great sound quality. Maybe your super-cool sibling can bust some dance moves while listening to that band you haven't heard of yet.

How to be a Man

First of all, do not buy this for your sister—this is strictly for carriers of the Y chromosome. I've purchased this book as a gift for several people and everyone seems to love it. 

The advice comes from the pen of Glenn O'Brien, gentleman extraordinaire and GQ Magazine's "Style Guy."

Keel's Simple Diary 2

Some people think diaries are lame, but these ones are super-funky-fresh. The Simple Diary takes the stress out of keeping a journal. Each page boasts a different quiz—because sometimes staring at a blank diary can be very daunting.

Lula Magazine

You've already bought Lucky subscriptions for everybody on your list. Make your sib feel special by also sending her Lula. All the cool girls love the twice-yearly UK publication from the U.K., known for ethereal and dreamy editorials. Although it comes but twice a year, it's always welcome and looks great on a coffee table.

Lego Volkswagen

Legos were fun for everybody when they were kids; you built castles, staged large-scale territorial battles between Native Americans and Spacemen and painfully stepped on them when barefoot.

But, when you consider Legos as something more than a toy, they become art.

Fab.com Gift Card

Well, if none of my suggestions are up to par, may I suggest a gift card to Fab.com? Fab is a great resource for furniture, art, accessories—pretty much anything made for the tragically hip. Not to mention: every sale is deeply discounted. So when all else fails, remember Fab.com! I recommend at least $50.