Yeah of course, if you're sculpting for a 3d illustration then that's how you'd do it. If this is being made for animation or as a realtime character then best to rig and pose the smile later.
So I said I would sculpt the concept but make my own clothes. I want to keep the clothes but add accessories. So I came up with this. Tell me If I should add or take away something or even start over.
The lacrimal caruncle in the inner eye area for the guy could be pulled close to the center of the head and more defined. Give the eye a little more body.
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But if you're not rigging it don't model them halfway down
Check out how theres that plane change around the eye at the top
Besides that digging e'erythang else.