Okay so after sitting on this for a day and looking through the suggestions that were given on the helping thread, here are the thoughts.
Outfit
To get my thoughts together, I made a kind of crappy sketch. In the end, this is heavily inspired by his canon outfit, but with some notable changes. Rather than a (weirdly fluffy) hood, he has a cape, structured the same way as Lillie's dress and falling at about the same length--but the design decoration the edges is lifted instead from Nihilego. This then is simultaneously family and the thing that ripped his family apart, all of which are things he tried to put behind him (metaphorically, but here physically as well.)
In the front it's Team Skull, with the logo closing the cape, and under that the same tank top worn by Team Skull grunts, except with the colors inverted. The shirt is white rather than black, and I haven't yet decided yet whether the X is black for a perfect inversion or red to keep his color theme intact, but either way, it's the wrong colors to blend in (because he's not really one of them, and he never will be.)
Under all that? It's the same ripped up black shirt and pants and worn in shoes from his canon clothes, because that's what he is. A homeless stray who left one life, never fully fit in another, gets knocked around, rips up his clothes, and then just keeps on wearing them because he's not sure what else to do.
Weapons
His weapons are where his Pokemon show up, which is only fitting for the canon, if a little ironic considering his bond with them is much stronger than someone who would only think of Pokemon as tools for fighting.
His melee weapon is a pair of kama, exactly as pictured there, designed in a way reminiscent of Type:Null/Silvally. The idea of using kama does pick up a little of his intense association with his main pokemon, since using them would not be unlike slashing with Null/Silvally's claws.
His ranged weapon will be a gun similar in design to this except with a smaller secondary set of wing decorations and the main color being purple and the accent being blue to mimic Crobat, which is the other pokemon he has throughout the game. (There are more on his team, but Zubat/Golbat/Crobat shows up in the most battle aside from Null/Silvally so it seemed like the right one to go with.)
no subject
Outfit
To get my thoughts together, I made a kind of crappy sketch. In the end, this is heavily inspired by his canon outfit, but with some notable changes. Rather than a (weirdly fluffy) hood, he has a cape, structured the same way as Lillie's dress and falling at about the same length--but the design decoration the edges is lifted instead from Nihilego. This then is simultaneously family and the thing that ripped his family apart, all of which are things he tried to put behind him (metaphorically, but here physically as well.)
In the front it's Team Skull, with the logo closing the cape, and under that the same tank top worn by Team Skull grunts, except with the colors inverted. The shirt is white rather than black, and I haven't yet decided yet whether the X is black for a perfect inversion or red to keep his color theme intact, but either way, it's the wrong colors to blend in (because he's not really one of them, and he never will be.)
Under all that? It's the same ripped up black shirt and pants and worn in shoes from his canon clothes, because that's what he is. A homeless stray who left one life, never fully fit in another, gets knocked around, rips up his clothes, and then just keeps on wearing them because he's not sure what else to do.
Weapons
His weapons are where his Pokemon show up, which is only fitting for the canon, if a little ironic considering his bond with them is much stronger than someone who would only think of Pokemon as tools for fighting.
His melee weapon is a pair of kama, exactly as pictured there, designed in a way reminiscent of Type:Null/Silvally. The idea of using kama does pick up a little of his intense association with his main pokemon, since using them would not be unlike slashing with Null/Silvally's claws.
His ranged weapon will be a gun similar in design to this except with a smaller secondary set of wing decorations and the main color being purple and the accent being blue to mimic Crobat, which is the other pokemon he has throughout the game. (There are more on his team, but Zubat/Golbat/Crobat shows up in the most battle aside from Null/Silvally so it seemed like the right one to go with.)