When creating my characters for my game idea, I had two simple outlined shapes that I knew would translate well in my game whether it was fully developed or not. The two main characters I had in mind were "Death" and "Time"; I knew these two both with opposite attributes and morals could work together somehow. Death was the lead character, he would strive for his own goals and ignore other's demands. He aims to fulfil his reaping list and with one more soul to recover, he has no time to mess with anyone else. 
Except Death's last soul to reap is the very person he ends up teaming up with, "Time". Time originally portrayed as a young child with pigtails and a dress has gone through the most changes in design. The next version of them I drew was a more unified look, with no immediate gender portrayal but rather looking like a minion of sorts. They donned a top hat upon their skeleton head and still kept a dress of sorts but this time it was accompanied by angelic wings. This was a child no more as Time was now a Cherub. 
But I still wasn't satisfied as one of the original game mechanics Death had was to kill skeleton enemies, If I were to keep this mechanic and keep "Dead" images solely to Death's character then Time had to go through another major change in character design. I in one week of my development of my idea created a whole sheet of breaking down the character styles I already had into their basic shapes and colours. Death was made of triangular shapes whereas as Time was more spherical, Perhaps if I made Time's design smaller and wider it would work well paired with the two designs of Death that I had currently made final and never to change again unless necessary. 

Death Character sheet

When creating my character "Death" I used the basic triangular shapes of a wizard and black and white colours to show some negative space. I first experimented with fading colours as you may see on the left-hand side. I then tried to make Death with two reflected shapes but ended up using a pointy head with two pointy legs attached to fill in later with some rectangles and a skirt cloak piece. I tried inverting the colours on the smaller designs switching between black and white as the main colours. These were what I depicted in my original concept drawings. 
Older design evolutions

Till death do us apart and other game ideas character sheet

First TD-DUA character sheet with enemies

Another archived design that has not yet been updated with these newer designs is their weapons. Death was originally paired with a sword his staff. Death would use these to battle enemies and unlock doors/solve puzzles. Time's weapons included a lantern and a scythe with a clock face embedded in its curved tip. 

Time character sheet

Time was the second main-game character I wanted to focus on, I first copied in my two Death designs from earlier to work as a reference when scaling down my finished work to make sure both were the same scale and would work well together in comparison. Time's design is more spherical and round than Death's, when translating my sketch drawing sheet version to a digital version, I found a picture of a Pokémon that looked a lot like my idea. I included this on my reference sheet alongside some extra pieces I didn't use. 
I also have some line-drawn ones as well as my final drawings of each design with a blue background behind them to show off the basic shapes. I initially wanted it to have a white cloak but bluey grey seems more fitting.  Upon some feedback from classmates, I have taken into consideration some steps to take to make Time more distinct from Death by making Time's hood less pointy and more curved like a jester hat.

Mood board to Make Time.

When showing my character designs to the class, I received a lot of great feedback. Most people adored my Death design and others who saw Time could not think of a similar design other than the Pokémon I already had on my reference sheet.  But one piece of feedback made me strive to redesign a key aspect of Time's shape; their head shape. With Death's overall design being pointy, having Time with Curves was great but their hood made this problem stand out.  So I decided it was time to update to Time's character design. 
I initially thought with the help of the classmate who gave me this feedback idea in the first place of a jester's hat. Time in my game story was portrayed as being childish but also silly. So I grabbed a few simple variations of a jester hat and began work to find the right head style. Some horns I made earlier were used at the start but without a border covering the head like a hood had done before, it looked bland to me. 

Time with its new jester hat alongside its development and evolution.

Time character evolution with the new final designs which I now have to choose from.

After some consideration and feedback from my classmates, I decided to change the eye shape to a half-diamond triangle to fit the expression on time better. I also made some of the lines more curved on the body and the jester's hat to further present that Time has a spherical body shape over Death's pointy body shape.

making the eye in Time more fresh

Time, new eye, blue hat

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