This is the Con Packing Checklist. It's original designed (by someone else) for Comic Con, but is a good way to make sure you leave home with everything you need and don't return home short a charger or shirt.
That's right, we're gonna stuff that mess of clothes into that bag right there.
Included we will be packing seven t-shirts, one knit dress, two skirts, three pairs of jeans, and three pairs of thick basketball shorts.
The way we're going to do this is by rolling almost everything instead of folding. Folding sounds like it makes sense because it's what everyone does when they do their laundry, but that takes up a lot of room, and if you're trying to stuff all your clothes into a carry-on bag then room is something that you do not have.
The first step is to lay your shirt flat and tuck in the arms. Otherwise you end up with weird fiddly bits hanging out the ends that will take up more room.
Then roll it from the neck down to the end. It's very important to go from the neck down, otherwise it doesn't end up even and then it's a whole mess.
Bonus picture of my puppy trying to be a helpful kitty.
This is what those shirts and shorts and skirts folded up. Notice that the three thickest items (both pairs of jeans and the dress) are folded directly in half instead of rolled. This is because rolling denim takes up a lot of room and a knitted dress with an odd shape will not roll well (you can see it rolled up and out of the way in the previous picture).
This is the empty carry-on bag that we're going to be fitting everything into. Notice the two bars splitting the inside of the bag into thirds. When you fold clothing, that is a lot of space that gets wasted right there, because the bars eat about an inch or so of space when you lay things flat over them.
So instead, we're going to take the thickest of our rolled clothing items and fit them along the sides of the bars. The ball of plaid in the top right corner is one of the skirts. It's actually thin enough that one rolled it could easily be folded in half and fit into a corner with a pair of the shorts.
Now all we have left is the shirts, jeans, and dress.
This is a side view to show how much more room there is still left. We've only really used less than half the space in the bag.
Next we're going to take our rolled shirts and fold them in half, then fit them around each other, and in corners, and anywhere else that we can. It's a little bit of a game of Tetris at this point, and you may have to change the layout a few times till you get it right.
This is a better view of what it looks like when you're standing. Notice there's still a little rectangle of room in between all the shirts. You can stuff socks or underwear here, or a hair brush, or whatever.
Now all that's left are the jeans and the dress.
The first pair of jeans you're going to just lay over everything else. Tuck it in a little if you can, but don't worry if you can't.
The second pair of jeans is where we want to pay attention though, because you want to make sure they mirror each other. We lay the second pair of the first, and the fold of one pair is sitting over the waistband of the other. This is because the waistband and hem of the bottom are going to be thicker, so if they're both facing the same way it's going to be lop-sided and lumpy, as opposed to even like it is here.
Next is the dress. It's already folded in half, so you're just going to fold it one more time and then lay it over the jeans.
This is what it looks like from the side. I know it's a little worrying, but literally all we need to do is pull it closed and zip it shut, tucking in anything that the zipper might catch.
And this is what it looks like when closed! Personally, I tend to use the zippers on the front pockets for this like soap, deodorant, toothpaste, my toothbrush, and other hygiene things that I don't particularly want to put near my clothes.
In addition, I also have two different "purses" that I use basically just for when I need to take my laptop somewhere. Most airlines will allow you a single carry-on item and a purse or backpack. You will want one that is designed for laptops, that way yours can be secure and not knocking around into your pens or books or makeup. You can buy them at Walmart, Best Buy, and many other places.
In addition to all this I always take a hoodie with me when I fly, not for the warmth, but for the extra pockets to store small things in. Bonus, they can be folded into a pillow for your flight.
One last little bonus piece tip is to wear your thickest clothes when you fly, and don't be afraid of layers, because those are just more things you don't have to fit into your bag.