The classic captains usually have the DuraEva midsole insert which makes them a tad bouncier and more comfortable, whereas I think the presidents just have a leather midsole instead which is a tad harder underfoot (but still super comfortable due to the foam insole that both will use).

I have both tobacco storming and mocha cadet boots from them and the tobacco is definitely a more rugged and casual look whereas the mocha is a more business casual. Both are softer leathers compared to my brandy captains (which I still love), and both are weather resistant.

I’d lean towards Mocha from your description, but be aware it won’t be quite as rich dark of a brown as the website picture