Help me pack, and win!

I'll be living out of one small bag for three months, so how do I stay looking haute instead of homeless? Share your packing tips with me and you could win a fantastic piece of luggage from Holiday Group

I’ve been agonizing over what to pack ever since I booked my trip. I’ll be away for just over three months, traveling to huge (and chilly) cities like Beijing and Tokyo, but also basking on the beach in Bali and Costa Rica. And I’ll be backpacking…like a grown-up, mind you (meaning the pack has wheels so I don’t throw out my back). So, my dilemma is: what do I bring to make sure I don’t look like I’ve crawled out of a tent when I’m going out for dinners in the city while still including enough practical stuff so that I don’t end up on a jungle trek in my skinny jeans.

I’ve started making a pile of all the backpack-worthy contenders in my closet and medicine cabinet: a few great washable, inexpensive Old Navy dresses, my favourite Fidelity skinny jeans, some t-shirts, jean shorts, my Gosh dry shampoo (cause I’m the type of girl whose hair is, for some reason, constantly greasy), the La Perla bathing suit I paid way too much for, flip-flops, hiking boots, and my electronic gadgets. That’s about as far as I’ve gotten.

This is where you come in. Have you been to any of the places I’m going? Do you have any great tips on what else I should pack?

Share your suggestions by commenting on this post and you could win the stylish (and super practical) suitcase you see pictured here, courtesy of Holiday Group. This 16″ wheeled tote is part of the Atlantic Compass Collection and sells for $140. It’s easily maneuverable over any terrain, includes a variety of smart organizing features and has plenty of interior space.

I’ll be gathering up your tips while I finish packing over the next week and a winner will be drawn on December 27th right before I leave for my first destination, Hawaii.