Old Spice put out a mildly amusing homebrew class for 3.5, the Gentleman. I decided it would be mildly amusing to make a version of it for 5e.
The College of Gentlemanly Behavior
Beginning at 3rd level, while you are not wearing armor, your Armor Class is equal to 10 + Dexterity Modifier + Charisma Modifier.
Beginning at 3rd level, you may expend a Bardic Inspiration die as a reaction when you or an ally within 30 feet of you deals damage to an target, rolling the die and adding the number rolled to the damage dealt. When you do so, any 1s or 2s rolled as part of the damage may be rerolled a single time. The target must be able to hear and understand you.
Beginning at 6th level, you can attack twice instead of once when you take the attack action on your turn.
Beginning at 14th level, the clothes you wear provide you with a nigh-magical bonus. This bonus depends on what kind of clothing or armor you are wearing.
You have advantage on ability checks made using Strength or Constitution. Additionally, once per short rest you may add either your Strength or Constitution (but not both) to any ability check made using Charisma.
If you roll below an 11 on a Deception check to disguise yourself, you may treat the roll as an 11. Additionally, you learn Disguise Self if you do not already know it, and may cast it without spending a spell slot.
You have advantage on all skill checks made to interact with nobility or other members of the upper class. Additionally, you Charisma score is increased by 2, to a maximum of 22. Traveller's Clothing: You no longer need to consume rations, your carrying capacity doubles, and your speed is increased by 10 feet per round. Additionally, you may take the dash or disengage actions as a bonus action.
When you are subjected to an effect that allows you to make a Dexterity saving throw to take only half damage, you instead take no damage if you succeed on the saving throw, and only half damage if you fail. Additionally, you may choose to use your Charisma modifier instead of your Dexterity modifier when determining your armor class.
When an attack would hit you, you may expend a use of Bardic Inspiration as a reaction, rolling the die and adding the result to your armor class until the end of your next turn. Additionally, you may choose to use your Charisma modifier instead of your Dexterity modifier when determining your armor class.
When you take the Attack action, you can attack three times instead of twice. Additionally, you may expend a use of Bardic Inspiration when you make an attack, rolling the die and adding the result to your attack roll. Your target must be able to hear you.
Thoughts and explanations:
Unarmored Defense is the Gentleman's Fancy Clothes, obviously.
Sharp Words is the subclass's special use for Bardic Inspiration (College of Valor lets their allies add BI to the damage of their attacks, and the College of Swords gets flourishes that let them add damage to their own attacks, but the Gentleman gets to do so as a reaction, and to both their own damage and others). It's also the equivalent of the Gentleman's Punchline feature (while Bardic Inspiration itself is similar to their Catchphrase feature).
Extra Attack represents that the Gentleman has a full Base Attack Bonus progression.
Infinite Wardrobe is the equivalent of the Gentleman's Wardrobe change - getting special bonuses based on what you're wearing. I threw in options for the armors as well because I felt like it, and it's perfectly possible to multiclass or be a dwarf to have proficiency in them. I didn't feel like making an option for every single armor though) Common clothes give you strength/con based bonus with the thought that you're in something like a peasant's tunic and showing off your strength. Costume clothing should be obvious, as should Fine and Traveller's. Light Armor gives you evasion with the thought that it's a little more protective that just clothes and therefore, while you might not be able to dodge as well, you can block damage by dodging most of it and absorbing the rest. Medium Armor lets you boost your AC mainly because I wasn't sure what else to do with it. Heavy Armor lets you attack a third time (and boost your attack roll) with the "knight in shining armor" idea.