If you ignore the flavor, assassin as a master of disguises, surprise master could work. If you just color the character more about thievery and less about murder (which any thief will be doing enough of anyway) you might get something that matches your play style.
I think if you want the heart-of-gold personality, Swashbuckler would be the best choice as it would mechanically reward you for increasing your CHA score. You could play any subclass and just roleplay as that personality, but swashbuckler will mechanically support that roleplay.
Going for a charismatic bandit-with-a-heart-of-gold trope style character. Leaning towards Swashbuckler, but am unsure.
If you ignore the flavor, assassin as a master of disguises, surprise master could work. If you just color the character more about thievery and less about murder (which any thief will be doing enough of anyway) you might get something that matches your play style.
I think if you want the heart-of-gold personality, Swashbuckler would be the best choice as it would mechanically reward you for increasing your CHA score. You could play any subclass and just roleplay as that personality, but swashbuckler will mechanically support that roleplay.
Swashbuckler... ask DM for mounted combatant for free.