Rapha, nice but a bit pricey?

Yes, thin canvas shoes like Vans will fit. I routinely fill mine with everything you've listed and sometimes a pair of Vans. You need to pack the clothes neatly and you are packing it to the brim but in my mind that means it's the perfect size.

My experience as well. I can get an 11" MacBook Air, change of (non-bulky) clothes and a pair of Adidas SL73 just about into mine if I pack very carefully