Anyone play like this? Too me it makes more sense for an assassin to look like he's not an assassin, versus walking around dressed head-to-toe in Dark Brotherhood gear. It just struck me as kind of odd that the stereotypical assassin build in the game involves wearing armor, instead of just regular clothes. Thoughts?

Yeah it's fine. It depends how you play. If your a more aggressive assassin, then some light armor (with no armor perks) and steed stone is fine enough. If your playing it strictlly in the shadows, then armor is pointless.

I should mention I'm thinking more about a DB contract type assassination, that generally involves going in public places. If sneaking around in some Draugr dungeon obviously armor makes more sense.

Depending on how you play, you can get through 100% of the game in clothing as an assassin, but you would have to play it strictly by the shadows almost all the time and you would need to be able to take out any target (minus a dragon) in one hit to increase your survivability chances.

A more aggressive assassin, which is me, I wear guildmaster armor, guildmaster boots, stormcloak officer bracers, and a circlet. I have a variety of light armors that range from 230-290 armor rating, and I don't see the point of needing more armor rating than that.

Contrary to popular belief Ninjas did not wear all black garb and armor, they would typically disguise themselves in common monk robes or clothing. So I see nothing wrong with wearing plainclothes as an assassin.