I'm trying to play a Redguard dual-wielding scimitars (as Rayya does), but this detail is getting in the way.
I don't think you can. I have always had to left and right click on my character's weapons from the favorites menu.
Not a dumb question at all. I wish I had a better solution than what King Coin mentions.
If they're the same weapon and not upgraded then you can hit the same hotkey button twice to equip both, same as with spells.