Probably far from the best option; but you could use 7zip? Put a 7zip portable exe & linux binary on the usb, put the regular contents in an encrypted .zip file, anyone with the password can decrypt. I assume there are much more secure options though.
7zip encryption is solid, but the problem with this is that you don't Mount 7zip, so you have to extract it. Once you extract encrypted files into a drive thats not encrypted, they may as well never have been encrypted in the first place.
Its better to use a tool that creates an encrypted filesystem that you can mount and read-write directly without copying the files onto another disk
ZIP isn't a good way to encrypt, but what Microsoft is doing is simply reading the email, and decrypting zips with the password found in the email body.
All encryptions schemes can be trivially broken if you have the key. It's not even breaking, it's just normal decryption.