Laptop bag suggestions

Greetings,

I’m in the market for a decent laptop bag that I can use both around town and at work. Looking for something that looks professional but is also appropriate for just casual use in various places. I’m looking to spend no more than $150-$175 on it. I want something that’s going to last for many years. I usually carry the following: A 13″ MacBook Pro, USB-C hub, MacBook power adapter, some pens, bottle of Tylenol (gotta love work). I would like to sometimes be able to fit my 12.9″ iPad Pro and a game controller in there. I feel like that’s a lot of stuff, but I’m sure people carry more than that. I live in the Atlanta area, so it does rain out of nowhere here so good protection from the rain is essential.

Thanks for your ideas!