Time for my next little RP oriented builds. This time i am doing the Rogueish classes the Bard and Pirate

Bard
Race: Any
Skill Trees: Speech, Sneak, Illusion, Enchantment, Alchemy, 1H/Archery, Light Armor (optional)
RP Items: Complete the Bard's College
Stone: Lover, Lord, Shadow
Shout: All Shouts
Discussion: I was disappointing by the fact that a Bard College exists in skyrim but you cannot play instruments, so the focus of this class are the Thu'ums. I know some people do not want to be dragonborn but the shouts would count as the "power" of your words/music/poetry or whatever. Otherwise you will be using Archery or 1H weapons (your choice) when you are not sneaking past the enemy. Using Alchemy and Enchanting will make up for your lack of "nailed down" combat ability. Illusion will also be a very RP friendly addition as you will sway the emotions of people and calm them down or even turn them against each other. Speech is the main skill you will be using as it will get you more money, better prices, more options in quests, etc. Now my bard does not wear armor but if you really need it go with light armor.

Pirate
Race: Redguard, Imperial. Orc
Skill Trees: Pickpocket, 1H, Sneak, Alchemy, Speech
RP Items: Scimitars
Stone: Thief, Lord, Serpent, Steed, Tower
Shout: Any
Discussion: So a Pirate is a Rogue who can deal it out with a sword but does not fight fair. So alchemy is for poison, use them to gain the advantage against those with armor or magic. Pickpocketing + Sneak can even the odds even more by putting poison in the enemy's inventory or at least taking away their stuff. Speech is for better prices and "talking your way" out of trouble (bribing guards). Pirates do not wear armor so dress casual and always bring a follower. I recommend alik'r/redguard clothes for a close look. This class is difficult to play since it has no armor or magic so only thse who love RP AND a challenge should attempt it

Always remember that these are RP oriented and leave some comments with opinions and what not