Based on your packing list, I'll also vote for the Western Flyer, because of the shoes.

If it weren't for the shoes, I'm pretty sure the Pilot would swallow that load, especially if you put the clothes into a packing cube. I've used the Pilot for one-night trips in which I've successfully fit an Bose headphones, iPad mini, Macbook Air plus chargers, file folders, 2 dresses (one silk, one lightweight cotton), and a very stuffed 3-1-1 bag of toiletries.

The Pilot fit perfectly standing up under the seats on an AA 737, both in domestic first and MCE, leaving plenty of legroom to the side.