With Vanilla Skyrim you can have 1 follower, but if you're on PC and get UFO (search for it on the nexus, I'm posting from my phone so can't link it) you can have up to 15 followers!
So technically you could play a Ranger style character and have followers who are warriors, mages, monks, etc
I think UFO's the only real way to go if you want a true D&D type experience in Skyrim. I can't see why I'd ever want 15 followers. As far as I remember D&D parties really only went to about half a dozen, like in the cartoon. That I think is the sensible number, especially with Skyrim's rather dodgy follower AI.
My main character is a ranger, followed by 2 heavy housecarls, Mjoll the Lioness with her axe, and Aela bringing up the rear with another bow. Thus a party of five, three in the front (Mjoll, Jordis, Lydia), one in the middle (me), and one in the back (Aela). We are warriors, and we don't like mages or magic.
i would replace Jordis with Cicero, but otherwise i would have that same party. but i'm a mage, so it would be a mixed group.
Mjoll: staves. she pwns with two staves, and is accurate. maybe just one staff and a shield/weapon
Aela: bow and arrows, for obvious reasons
Cicero: idk. i choose him cos he's hilarious.
Lydia: heavy armour, sword-and-board.
me: magicz and shouts. light armour, sneak bow and magic attacks