I use lower end crossbody bags. Last trip I used my MbMJ preppy Natasha. It was bright, but the logo was printed on the leather but you couldn't read it from afar. It had a zipper flap pocket, where I kept my wallet and passport. The main compartment was large enough to fit an umbrella, camera, and water bottle. The pocket kept maps and ticket stubs.
Now I use my Coach Madeline, no obvious logo, but because I want to go to high end shops and restaurants, I didn't want something too casual. The pocket under the flap will be used for maps and ticket stubs. Inside zipper pocket for securing my passport. My wallet will be underneath my umbrella, camera, and water bottle, but it still isn't a bag easy to open because of the structured top of the Madeline. It's boxy and when you want to open it you have to pull apart the sides so it'll stay open. Otherwise it closes again. It's hard for me to describe lol. Also, it has multiple ways to carry with the adjustable strap.
Travel bag criteria: crossbody, leather, no obvious logos, or ability to turn the bag around to hide logo. Added criteria of being able to dress up or down. Various ways to carry is a plus.
Tote of course, is the trusty large Longchamp LP.
Even when stuffed full, it still fits under the seat in front of me. Worry free, water resistant.