1: Pick your bag. Check with your airline to see what their guidelines are regarding carry on bag sizes. Anything labeled as a carry on should be fine, but some may be larger than others. The one pictured here is a duffle (because my carry on bag isn't nearly as adorable), but I prefer a rolling bag with an extendable handle. They're much easier to navigate the airport with. This Lipault bag is one I seriously want to invest in. It folds up flat and comes with it's own storage case!
2: Plan ahead. Brainstorm outfits you'll need or want to wear on your trip (check the weather for your destination first!). Lay everything out and start mixing and matching outfits. I find it easier to bring items that can be worn in many different ways, that way you always feel like you have options without taking your whole wardrobe with you. That blue sweater that only goes with one other item you're packing? Leave it at home. Get creative here! Really stretch your brain when it comes to your vacation outfits. Try pattern mixing and color blocking. You're on vacation, have some fun!
3: Edit. Really try to limit yourself to one outfit per activity on your trip. Make sure you have a couple layering pieces in case the weather turns on you, but other than that, be strict! Shoes are my weak point. I will gladly sacrifice an extra pair of pants or two if that means I can fit another pair of my beloved shoes. Decide which items you absolutely have to bring and leave behind things you can survive without.
4: Pack it up. Shoes and other heavy items on the bottom. Tuck small items like socks or belts inside your shoes to conserve space. I feel every nook and cranny around my shoes with stuff - jewelry, underwear, bathing suit - if it can be scrunched into a little ball and shoved in there, I do it. Next, I roll all my clothes and place them on top of my shoes and accessories. Rolling things really does take up less space, and I think it keeps things from getting too badly wrinkled as well. I tuck my non-liquid makeup bag on top and then shove in any other accessories I need into the pockets, if they fit. The pockets on the outside of the bag I reserve for things I'll need to get quickly - my one quart clear plastic baggie, for example. Which brings me to...
5: The 3-1-1 Rule. The 3-1-1 Rule is the TSA's guidelines for carrying liquids on a plane. This really isn't as hard as you may think. This is where a lot of people give up and decide to check their bags. But guess what? You seriously don't need full bottles of shampoo and conditioner for a week away. Buy a kit of small plastic bottles and decant your favorite products into them. You can also get most of your favorites in travel sizes - 3floz.com is a great resource for every product you could ever need - in carry on friendly sizes! You can use a regular old Ziploc baggie to store your stuff, or you can get a more durable one. I just bought this one. Don't panic if you can't fit everything - get your essentials in the baggie. You're probably not going to the middle of the jungle, there will be drugstores, you will be able to buy more shampoo if it comes down to it.
6: The personal bag. In addition to your suitcase, most airlines also allow one personal bag per passenger. It just has to fit under the seat in front of you. I put my purse, my Kindle, my phone, books, magazines, travel documents and what have you in this bag. I got this great one from LLBean and it's got plenty of compartments for keeping everything organized. It also has a strap on the back to secure it to the handle of your wheeled luggage when you're maneuvering around. Handy! I don't like to completely fill this bag. It's great back up in case you accumulate stuff on your trip or just need some extra space.
