Highwayman

Rogues who walks the path of the Highwayman are rogues that focus more on the art of Combat and Intimidation as opposed to a normal rogues Cunning and Guile. Rogues who has the Archetype of a Highwayman are often at odds with the law as their preferred way of thievery comes from Ambushing travelers that are either unguarded or they don't see as a threat.

Scare Tactics

When you choose this archetype at 3rd level, you gain expertise in Intimidation if you have proficiency in it, if not you gain proficiency. You also gain advantage on saving throws against being frightened.

Imposing Presence

Starting at 3rd level, When you are targeted by a melee attack, you can use your reaction to do a Intimidation check against the attackers Wisdom(Insight), if the Intimidation is successful the attacker has disadvantage on the attack roll.

You can use this skill a number of times equal to your proficiency bonus per long rest.

Well Equipped

Starting at level 3. You can use Sneak Attack with any weapon you are proficient with. You also gain proficiency with Medium Armor and it no longer imposes disadvantage on Stealth checks while wearing it. 

Weathered Bandit

As a profession being a Highwayman most people tend to die young, you however, you are a tough sonova***** its this experience that keeps you alive. Whenever you make a Dexterity saving throw you can choose to use your Strength modifier instead of your Dexterity modifier, also for every rogue level you have at anytime you gain 2 extra hit points.

Robber's Mind

Starting at level 13, you can see trough any attempt at hiding valuables or valuable information (at DM's digression) from you, although you can not discern its location or what information is being hidden.

Dirty Fighting

When you take the Attack action, whilst not having disadvantage, and successfully land a not Sneak Attack hit, you can force the target enemy to make a Saving Throw against you attack roll for one of the following Conditions. You cannot use this Abillity on a enemy the same turn you used your Sneak Attack on that same enemy.

• You attempt to knock the target prone, the target must make a Strength Saving Throw. 
• You try to get in close and grapple the target, the target must make a Dexterity Saving Throw or be grappled.
• You throw sand at the target if the target does not make a Constitution Saving Throw, the target is blinded.