Jeans are always my fall back for chic and comfy, and for traveling I always wear a pair that has a bit of stretch to them for extra comfort.
On top I like to keep it loose with nothing to constricting. But that doesn't mean you have to get lazy about it, there's plenty of cute tops out there that are comfortable with out being plain and boring. Over that I'll through snuggly wrap cardi that's super soft! (I'll also usually bring a pashmina or big cashmere scarf to wrap up if I want to sleep on the plane or roll it up into a pillow.)
For accessories go light, cause you'll have to take everything off at security and there's no need to be worrying if you got all your rings and earrings or not. So just a simple watch and sunglasses in you favorite style should do it. And I always have my headphones when I travel, yes I know they're kind of hipster but I always listen to music on planes and this way I wont be bothered by pesky seat-mates.
As for carry-ons I don't bring much on planes, just some magazines and my laptop, (more on that coming later). And I am LOVING this Rachel Zoe tote from Nordstoms! But then I keep all my money, passport, tickets, etc. close to me in a small cross body bag.
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