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I love my Tumi briefcase. I’ve had it for years and it still looks brand new. You can also frequently find them on sale.
Literally looked at this post just to say tumi. I'm a fan of their older/vintage bags. They seem like higher quality / better leather if you can find one in good condition.
Buy a Halliburton off eBay.
I am slumming it with a sub-$100 Kensington backpack. But I have also slummed it with a sub-$100 backpack from Swissgear.