Gangster

Gangsters are fashionable rogues that operate both in and out of the shadows. Typically involved in organized crime, employed as bodyguards, or working as town guards, they sit outside the scope of most traditional enforcement. These men and women live bound by honor and traditions, which often puts them at odds with other criminals, and can lead to large scale conflicts. Despite this, individuals that have earned a gangster's trust find themselves to possess the most loyal of comrades.

Coveted Skillset

You have a skillset that's highly coveted among criminal organizations which includes firearm proficiency:
You gain proficiency with firearms and can use them to perform sneak attacks

Impeccable Taste

You have a suit that you use for your protection which makes your unarmored armor class 10+Your Dexterity Modifier+Your Charisma Modifier.

Fedora Tip

As a bonus action you can tip your Fedora which grants you advantage on all Charisma based skill checks for 10 minutes.

Moxie

When you make an attack with a firearm you can use your bonus action to make another attack with the firearm and you gain temporary hit points equal to double your rogue level. You can use this ability twice per short or long rest and you can give an ally within 30 feet the temporary hit points instead of you but you must still make the firearm attack.

Give 'em a show

You've become so good at fighting other people will watch the show you put on.
At 13th level you turn your fights into shows and you can add your Charisma modifier to your attack and damage rolls you make with Firearms.

Tough as Nails

You've taken many beatings at this point which is evident with how strong your tolerance for pain has become.
Whenever you use your Moxie feature, you also gain advantage on all saving throws until the start of your next turn. Additionally, if you roll initiative and have no uses of Moxie remaining, you regain one use of it.