I know shit about it but like the idea.
Tagging
@Husky_Khan because I haven't seen posters.
The idea is : werebear and wereboar shield and sabre-holding tricorn wearing procrastinator from the low middle class (don't know what it the equivalent in D&D).
Cook class.
Sorry I missed this.
You can play a Werewhatever class. It's perfectly acceptable depending on your DM/GM if he accepts it. Most of my experience comes from playing with actual friends so our rules tend to be pretty flexible but if your planning on joining an actual group, their rules or guidelines would actually be more stringent.
I'm not a big fan of "custom" classes and honestly 5th Edition is so flexible that you could just make a Fighter who likes to Cook. So he'd be a fighter... but also a cook.
As for the tricorn thing, that's fine. In my campaigns we've had an NPC character (for temporary players who kinda show up) who was Giff (a Humanoid Hippotami) who had the whole pith helmet and khaki shirt deal going on with the smoke powder pistol and rifle and primitive grenade and the like etc etc. Again... its your character so you can make your background as eclectic as you want
within reason depending on your GM/DM.
The important thing is that you shouldn't get too carried away with your backstory or whatever or go too crazy IMHO. Especially if your playing with "non-friends" they'll likely be generally ambivalent if you go overboard on your character backstory. If you want to show off your character, do it in the campaign as you engage in
role playing not in sharing your extensive eccentric backstory.
As for how to play Dungeons and Dragons. I would recommend getting the Players Handbook. In all honesty... the Players Handbook is really the only book you actually need to play Dungeons and Dragons (and to GM/DM it to be honest). Every other book (Dungeon Master Guide included) is really just nice to have.
If you haven't found a group right away, I'd recommend experimenting in creating characters and generating them and you totally could explore the combat system by setting up fights with your character and various monsters. It's totally possible to do since 5Eis a "wargame" with its core mechanics still. But 5th Edition is Role Playing as well and obviously... that's best with a group of people.
There's lots of ways you can create classes from beyond the normal races including lots of third party books or just accessing stuff on the internet.
If you want an example of how to play Dungeons and Dragons, I'd avoid the Critical Role
shit with the professional voice actors and talent on the internets... this is probably the best one IMHO. He has some custom rules as GM/DM but you'll get the idea of the game in general I feel.
But yeah, you could totally play a Wereboar
Cook Fighter (not sure about a Werebear, IIRC they are a fair bit more powerful) if you were in my campaign I would think. They're not terribly OP or can be modified to not be so.