I got a second belt so I can leave one in my everyday jeans. Works great. I tried a belt or two that are stiff to the point of being less comfortable and the big buckles can get in the way.
I thread the metal buckle through my belt loops as that tends to be the easier direction, and typically leave the belt overlapping a belt loop. My belt is typically covered so I’m not concerned about a tactical look. As for sizing: I’m wearing a belt the same size as my jeans.