I rarely write reviews but this bag exceeded my expectations and I'm upset with myself I hadn't purchased one sooner. I purchased this weekender bag last minute before a quick cross country trip to use as a carry on. It fit all of my carry on essentials (large headphones, laptop, notebook, magazines, some toiletries, sweatshirt, large water bottle, etc) and I had still had plenty of room. Side note: I am a chronic over-packer. I even was able to put my purse inside to have one less bag to carry. It's definitely a "black hole" kind of bag, so I used other small zip pouches to keep things semi-organized inside of it. The trolley sleeve is a game changer if you are traveling with a rolling suitcase. As others have mentioned, the zip pocket on the sleeve held my iPhone and boarding pass while walking through the airport (eliminating that moment of panic before you board when you can't find your phone or your boarding pass in your purse).I didn't use the bottom compartment for shoes so I can't speak to how well shoes fit or impact the room in the main compartment of the bag. But I did find the bottom zip compartment perfect for my laptop, magazines, a book and some other work related stuff. It's not as structured of a bag as the photos make it appear but that personally didn't bother me. I think it makes it easier to pack it full and put it under a plane seat or overhead compartment.It fit just fine under the seat on the plane (American Airlines). It held up great after 2 flights and 4 days of hotel hopping. The quality is far better than I expected and I personally find it pretty stylish and classic looking (I purchased the beige). Overall, if you're looking for a budget-friendly, useful, chic tote, I highly recommend.