Is there room for paper and pens too?

yes, I like this cause I gift to my father and he likes it.

Will this bag stand upright on its own without needing to lean on something?

Sometimes it does, depends on what is inside and how the contents are positioned. It does not have a hard base to always support an upright position.

Can this bag be used to carry laptop to the office too? I have MacBook pro 15 inches

My laptop is dell latitude e7440 14inch. This is fit ,not enough.

Is it genuine natural leather?

This is genuine leather, "At least it's genuine leather.", so it is natural. I use this slim now one year and it is good for small laptop or tablet.

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Samsonite Luggage Leather Slim Briefcase

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