I'm sharing my favorite weekender bag today. I bought it four or five years ago at TJ Maxx for $20 - I actually bought two, one for my sister (in black) and one for me (in the olive pictured below) - and I still think it's a great bag.
Here's just a quick shot of the back. The two zippers open up to the same compartment - I don't really know the reason for that but it's kind of neat.
There are two smaller side pockets which are great for socks and underpants but also great for glasses (in a case, of course) or electronics chargers or other things you might want to reach for in a jiffy, like maybe your allergy pills or a snack.
There's a handle and a strap, which is nice because carrying a bag, even if it isn't that heavy, can get cumbersome if you've got to travel a mile through the airport because for some reason, your flight is always the gate farthest away. So, you can shift the bag back and forth between hands and shoulders. The longer strap is completely detachable if you can't be bothered with it at all.
There's plenty of space in the main body of the bag and there's a laptop slot and a netted pocket. The netted pocket would also be great for your laptop charger but also great for socks and underpants.
There are a bunch of pockets in the front too, including little pen slots. I feel like these details would make this a great bag for a business trip as well. For leisure trips, I slip in a pen and journal in this front area.
This bag is the perfect size for packing three outfits, a pair of shoes, a laptop, and a bag of toiletries. I used this when I went to Houston and it was great. It fit comfortably in the overhead bin but if there hadn't been any room, it would've also fit under the seat, which is awesome. It's also weatherproof, which is nice. If you're in the market for a new travel bag, I suggest something with this sort of design, if you can find one.
Here are a few real-life suggestions that you could purchase today:
The pink Lipault bag is probably the closest thing to mine but the others are quite chic and functional as well. It really comes down to your style of organization. If you're a bargain hunter, might I suggest hitting up TJ Maxx, Marshalls, and other similar discount stores? Happy shopping!