The Moonlight Mask

The origin of this cursed theater ensemble and the play performed with it has been forgotten, a tragedy of star-crossed lovers and melodrama under the moonlight. The dingy hat has passed through many hands, some noble, some infamous, some both. Humanity seems to have stick, luckily, to it throughout this time. Even the most cunning outlaw ends up finding themselves on the side of good (for a given value of good...) when donning these items, a need to balance out tragedy with hope and revelry.

The trick is to add a white mask and some nice dress gloves. Worn together, they produce a classy noble ready for a night on the town... or perhaps some less wholesome mischief.

Gentleman Thief

Your lingering memories of being a brave treasure hunter and cunning jewel thief allow you to use supernatural cunning and guile. You have proficiency in Stealth and Slight of Hand. To help you better examine your stolen booty, you can use freely the spell Identify and Detect Magic each once per long rest.

Sharply Dressed

Your shadowy cape billows when dramatically appropriate, even in the still air. In dim or dark conditions, enemies have disadvantage on perception checks towards you.

You remember a thief in the night needs to willing to leap rooftop to rooftop. You may cast Jump, Knock, and Feather Fall at no cost once per long rest. 

You can also invoke the magic of your cape to protect you from harm. A number of combat rounds half that (rounded down) of your spellcasting modifier, you can give enemies disadvantage on slashing, bludgeoning, or piercing damage towards you. This ability resets after a long rest.

Dandy's Cane

You conjure a one-handed weapon to complete your ensemble. This weapon counts as magical, you are considered proficient in it, and can use your spell-casting modifier for the damage instead of STR/DEX. If you are disarmed of it, you can re-summon it back to your person as a bonus action.

Once per long rest, you may use this weapon to freely cast Mirror Image or Expeditious Retreat on yourself.

Eldritch Dart

You have learned and adapted the infamous cantrip to your own ends, taking the semi-physical form of darts, stilettos, or even roses. A number of times equal to your spell casting modifier per long rest, you can add an additional unique effect to the damage.

• Adaptive Dart: You can change the damage type of Eldritch Blast to piercing, slashing, or bludgeoning damage. 
• Blinding Dart: Targets have disadvantage on their next attack and/or any perception checks.
• Staking Dart: The target must roll a CON save  after being hit with the spell. On a failure, the target's movement speed becomes zero until they roll a success or three combat rounds have passed.  Variant Rule: On a critical fail, the target is outright paralysed for the first round.
• Debilitating Dart: Targets are affected by the Slow spell.
• Distracting Dart: Targets are affected by the Enthrall spell.

Rousing Encouragement

 A number of times equal to your spell-casting modifier per long rest, you may freely cast Bless or Heroism to deliver a pep talk to a quavering ally or fellow thespian in need.

You do not wish to be seen before your grand entrance to a battle. You have advantage on Stealth checks that rely on moving silently.  While moving, your steps make no sound  regardless of the surface you are moving across, and you can become invisible in dim or dark conditions while not moving.

Spectre

You cannot be charmed, and attempts to charm you are reflected back to the caster.

You can cast Jump and Feather Fall at will. You may also cast the Fly spell once per long rest without cost.

You cunning movement and guile acrobatics border on the ethereal. You are immune to non-magical damage in dim or dark conditions. When you are targeted by a damage dealing spell, you may use Counterspell freely a number of times half to your spellcasting modifier (rounded down) per long rest.