Your character looks pretty great to be honest, I've seen some horrible defiling of the Nightingale Armor, and I must say yours is some of the best, you can really tell the guy is a mage-assasin type, pretty cool.
That's the endgame set, to maximize the enchantments with minimal armor, and bare bones casting cost. (With an Altmer, Expert Illusion, the Robes, Nightingale Hood, and Gauldur Amulet, I can just barely cast Invisibilty without investing in Magicka. So, I could spend it all on Health.) Here's the Plainclothes, which you can get as soon as you clear out the Dawnstar Sanctuary:
If you don't know the DBH, he just looks like a high level Mage, and his Bodyguard. "See?" {Casts Candlelight.} For roleplay reasons, I never got walking into town for a contract in full Shrouded, and depending on the game to just ignore that an Assassin was seen right before somebody mysteriosly dies from a dagger thrust to the back, or a slit throat. (I still get the "Hail Sithis" comments from the guards in the hood, though.) So, I tend to go in disguise, or skulk in invisibly so it's not so blatant.
Incidentally, Eola is the perfect follower for an assassin, or Nightblade, because she fills in a lot of gaps. She's probably the best rounded NPC in the game, because she uses: Swords, Alteration, Conjuration, Destruction, Light Armor, and Sneak. Not unlike a PCC combination of Spellsword, and Nightblade (She only uses Invisibility once, in the MHotD.) The Ring really helps too. Jenassa's actually my second choice, because she doesn't use Magic, and I'm not throwing fire all over the place. They can both do the "Wait Here" in LoS while you sneak forward, then open up with support fire as soon as you land the Backstab...
