STORY 

I premise this is a side character I created time ago for a story, set in a fantasy universe, inspired to south-eastern Europe/XIX century.

The real name of my character is unknown or, better, forgotten: everybody called him “Squirrel” since he was a child, when he was a petty thief, very skilled on committing little crimes and disappearing, jumping on the roofs, hiding everywhere, just like a squirrel through the fronds.
Now he’s almost thirty and he made his way in the criminal world and he has the monopoly on the dealing of a particular drug in the city.
He is not a "criminal mastermind" and not even a super-villain, but he is enough clever and merciless to prefer not having to deal with him. 

I don't know if this is a good choice (please tell me what do you think about it) but, supposing he is part of a story, I don't want the reader to see and just say "Man! This one is a real badass!". I want the reader to ask how far he can go...

(ok... he is a very, veeeery funny character! I know -_-)

Squirrel likes showing off he is someone now and he has money. He mainly does it wearing jewels or buying expensive dresses and objects, but he is always and however shabby, squandering his belongings in alcohol, expensive brothels and unnecessary things, inexorably tending to chaos.
He might have been even a handsome guy, in his way, but he just can’t help it!!!

 

RESEARCH 

As the genre is low fantasy I felt free not to be historically accurate and to mix up a bit of this and a bit of that (how clever I am! LOL). I found tons of inspirations, searching for east-european painters, historical photography of that zone, but also gipsy, turkish, bohemien and people whose features just inspired me for this character.
This is an extract of what I collected:

 

CONFESSION MOMENT

I just love drawing faces... and when it comes to bodies I don't feel completely at ease. Actually, I'm doing this class for a reason! I want to overcome this obstacle.

Anyway, the temptation to draw his face first was too much strong! So, here it is a portrait of Squirrel

I don't want to make him too cartoony, but I tried to exaggerate his features a bit anyway. 

One thing I absolutely want to see in him is a rat like face... another reason why people named him like this (but I suggest not to tell him).
Searching through some old mug-shots on the web, I noticed that many of them were physically “damaged”. He himself must be passed through many misadventures in his life: I want him to have crocked nose and a pair of gold teeth.

Ok. Time to draw the body, now!!!

 

ROUGH

As a child, I imagine him tiny and slim, but now that he is a criminal through and through, I want him to be grown up also in his height. Being slender and quite tall, and no more the "little slip of a thing", might be even some kind of "redemption" for him.
I thought the rectangle might have been a good choice.

 

It might seem weird but this part was less easy than it seemed. I never thought drawing the sticky man could have been so difficult!
Choosing a curve for that rectangle wasn't banal at all.
I wanted his posture to be lunky, not elegant, not upright... however it didn't have to be bent, insecure. 

Anyway, once out of the sticky man tunnel, I thought about the pose. Same line of reasoning:

Another difficult thing was exaggerating the proportion. I tried to work more on the rhythm... long-short, curve-straight/angles, large-narrow.

For what regards the colors and cleanings... I like to give a rough feeling unless it is requested... I'll do it in the future, because giving the same sense of dynamism with clean lines is not easy, I know! 
But, for the moment, I decided to leave it rough.

I hope you liked it and sorry for the lenght.

 

 Note: I can't see the final pictures in the app... I hope you can see them :/