Jimcamx posted...So what are the coolest looking things to Enchant in this list?
That is wholly subjective... especially on your class and preferred style of dress.
I'm fond of combining the Mourner's gear (from Radiant Raiment) with Thalmor Boots and Gloves... Makes for a very interesting combination.
Ulfric's Clothes and Boots also look awesome, though his gauntlets are armour for some reason and don't actually show properly on the character model.
The Emperor's Robe makes for an awesome mage robe... and there are multiple copies naturally available without duplication if you don't like cheating.
BUT none of this matters much compared to the various Psijic Robe parts.
Yeah, I know, they're on the unavailable list... BUT, unlike some other clothes like Nocturnal's and the Greybeard Robes, they are actually visible in the inventory and can be enchanted like any other clothing... assuming you can get your hands on them.
And THAT is as simple as using the Barrel Hex-Edit method... if you can find out how to do that.
(Note 1: Psijic Robes come in 4 parts, for extra enchantedness.)
(Note 2: Psijic Robes make female mages look fat. Dead serious. Not necessarily a bad thing though.)