I'm not sure, but normal apparel is probably not counted against your encumbrance limit. It's just that when you move armor into your backpack, its weight gets added back to your encumbrance limit.
That explains it; I've been wondering how and why it works that way. However I've now discovered the only reason I'm having an issue with this is because half of my mods (one of which includes encumbrance rebalancing for certain objects) keep unchecking everytime I start the game. Problem for a new thread I guess.

Edit: Making the appdata/skyrim folder read-only seems to have done the trick. This thread feels somewhat redundant now