Packing is by far the worst part of every trip. As was my case, I wanted to bring too much. I would unpack some, and eventually leave behind the best options. I have since learned to pack just a bit better from my aunt who can pack 2 weeks of clothing, and toiletries into a carry-on sized case. I am not as good as her at packing, but she taught me that it is all in the preparation.
When you pack, keep a running list of things you generally need on a vacation to jump start your packing. Depending on your activities, it is probably best to bring a couple of outfits per day, one casual, one evening, both with shoe options. Along with oral hygiene, and skin care products, list travel specific items per environment like sunscreen for a beach getaway, bug repellent for rural visits, wet/dry shoes for swimming, or a travel size fragrance for a nice evening out. After gathering everything you desire for your trip, lay it all out to be sure nothing is overlooked.
When starting to pack, start with the heavier items. Place things like Dopp kits, and electronics bags, at the bottom of your suitcase near the wheels for stability. Once you have bulkier objects packed, roll jeans from bottom to top, and for sweaters and t-shirts, fold in the sleeves and roll from the top. Lay the rolled items in the open spaces between the heavier gear. The curvy open spaces near the bottom of your suitcase are a great fit for shoes. Inside those shoes, you can stow pairs of socks, belts, fragrance, or other accessories. For more delicate accessories, pack them at the top, so they are not crushed by the heavier pieces.
For even more delicate items, layer them between shirts, shoes, and jeans as a cushion. Keep in mind to pack items you will need quick access to at the top of your bag too. Atop everything else, you can fold a sweater, jacket, or coat to protect inner items from creases and prevent slippage in your luggage. The flat area here will also help you zip your bag easier. Now that bit is over, you will find packing for a trip is not so bad. Enjoy.