First, no matter the length of the trip or the destination, you'll need a packing list. This will help you (1) think of everything beforehand instead of while packing, (2) check off items so they are not forgotten, and (3) have a "packing out" checklist to ensure that everything you brought finds its way back home. Check your hotel(s)' amenities before completing your packing list. For example, you may be able to leave your hairdryer at home or there may be a fabulous fitness center or a tennis court that you'll want your workout clothes for. Here's a great pre-made packing list from Pinterest that can be a starting point for your own list.
Clothes
For your clothes that require ironing, save yourself the trouble of ironing on vacation. Iron the clothes beforehand and put them in cleaner's bags. This will provide a shield for the clothes while they are traveling and also a slippery surface that will reduce the chances of your clothes wrinkling.
If you're going on a road trip, leave the cleaner's bags of clothes out of your luggage. After filling your trunk, lay the clothes flat across the baggage. If you are flying, going by train, cruise ship, or whatever else, save those bags of clothes for the last stage of your packing. Gently fold the bags of clothes and secure them across your other items in the bag.
For clothes that do not need ironing, like gym clothes, PJs, bathing suits, underwear, etc. or materials like denim, rayon, lyrca, and polyester, you should roll them before packing. Rolling saves space and also, counter-intuitively, crunches the clothes up less than traditional folding. Small items like socks, underwear, bras, tights, etc. should be made as small as possible and put into extra spaces found within other items, like shoes and purses.
Don't forget to pack an extra plastic bag or two for wet bathing suits, hair towels, or dirty laundry for the trip home.
Toiletries
Shampoos that strip your hair, conditioners that are pretty worthless - hotel toiletry quality is often the luck of the draw. If you're looking for quality, but aren't necessarily wed to your everyday products, try luxury brand sample sizes, like from Birchbox or from some of your local beauty supply stores, so that you don't have to sacrifice great products for small sizes. Go through your daily routine (morning and evening) to be sure you account for everything you'll need to get ready for the day and for bed.
Food
If you have special dietary needs that you are unsure will be met where you're traveling, pack some emergency snacks like Larabars, trail mix, or other items that will suit your needs without being perishable in your bags.
Using Space Wisely
The basic principle I use when packing is to use every single inch of space wisely. This means phone charger, camera, and laptop charger in a purse; underwear and tights in shoes; anything TSA doesn't need to scan in my makeup bag or flat iron case. USA Today published a good article on how to make to most of your space, TSA's policies, and amenities on the road. Real Simple also had a helpful article for dealing with clothing-heavy packing.
In the end, don't stress too much about remembering everything. Unless you're going on a safari or ice fishing in Antarctica, the place you're traveling to will likely have stores where you can get what you need. Bon voyage!
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