Wheels Up! Win The Utility-Chic Gypsy Moth Flight Bag By Crumpler

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Here's how to tell that you're a traveling superstar: Packing a bag no longer feels like a daunting task, but an exercise in editing. You know what you need, how to carry it, and if you're stuck toting your goods around (how many times have we left straight from the office?), you aren't doing so with your college-era duffle. In fact, having a go-to carryall that doesn't inspire dread is a major step towards honing your travel Zen, which is why the cosmopolitan-meets-utility Gypsy Moth Flight Bag by Crumpler is the perfect go-anywhere option.

With an over-the-shoulder component transitioning into a briefcase-like tote, you could take your Gypsy Moth from a meeting to the plane to a dinner — with only a few adjustments. Featuring ruggedly sharp criss-cross straps and pearl-finished metal fittings, the Gypsy Moth is a beautiful piece of design, and one that stands up to whatever your jetsetting life throws at you.

So, whether or not you are a traveling pro, you can fake it by scoring your own Gypsy Moth Flight Bag by signing up here and entering for a chance to win one to call your own. Finding the adventures to take it on, unfortunately, is all on you.