Hokay, I've been debating his outfit for, hrm, a few years at least, and still largely coming up blank, so I'll just use my version of him on Soul Caliber III as a basis. (Wish I could get a screen shot, but don't have the proper hook-ups to get it on my PC)
 
I'm not sure that pure description will get my ideas across, so I'm tossing in some reference pics to help. Please note that I'm not one of those "do this exactly as I say or its no good" sort of people. If something strikes you as out of place, or if you get a creative spark that would add some flavor or coolness, by all means, let it flow :)
 
For starters, I've always envisioned him to look much like Jake McCarthy from the Witchblade comics. This was always the pic I kept close at hand while gaming: Jake
He always looks like he hasn't shaved in a day or two. His eyes are a bluish-grey (not sure if that'll even show in the pic, but throwing that in here just in case).
I know its out of style nowadays, but I'd like him to have one of those long, thin braids of hair coming out the back, simply so I can add a touch of his elven ties in, by having it hanging somewhere in the pic with a colorful feather or three tied into it near the end.
 
Oh, yeah, if it helps, in the most basic (D&D) terms he's a fighter/rogue/wizard, primarily uses the skills together as a superspy/assassin type, to give you some idea of what he does in general.
 
He's fairly well built where muscle is concerned, but not overly bulky, as he's still supposed to be agile, acrobatic, and all thiefly. His height is just over 6 feet, in case that matters for reference.
 
As for the overall "theme" of the outfit, I'd have to describe it as gritty and well-worn, meaning that the colors are faded, the edges are tattered, etc. 
 
The basic components are black leather pants (probably with a lace-up crotch to fit the time period/fantasy setting I primarily play him in; for reference, he's a multi-genre character that I've adapted to a few different gaming systems now), and a faded charcoal sleeveless shirt (I think something along the lines of a regular old cotton tee or whatnot as opposed to leather on this one, though I leave it open to interpretation as I've never made up my mind on what fits best with the rest of the outfit).
 
A pair of gothic-y boots will work nicely, though I'd like something that comes just over the knee (I suppose sort of with built-in knee pads/protectors of some type).
 
For the hands, I'd like fingerless leather gloves, that come partway up the forearm, with straps around the wrist area. Something along those lines. If possible, portray it as gloves with thick leather bracers of some sort that attach to them. Room to play with the concept of those, I just need to fit in the fact that his D&D magic items consist of both magic gloves and magic bracers in some way or another.
 
For a splash of color, he wears a blue-grey scarf (that can alternately serve as a face mask and/or hood as well, when situated correctly). Of course, for the pic it should hang low enough in the front so as not to actually obscure his face, heh.
 
Hrm, what's next? Ah, yeah, the waist. I'd like to have a waist wrap of sorts, like in this reference picture (the light brown part in particular). Its a Scottish tartan (plaid kilt stuff), whose primary color would match the scarf mentioned above. I'm not sure if secondary colors, or even the pattern, would show, but if so, I'd like to trust your judgement on choosing them. This is his homage to family heritage, though I'm not willing to actually have him wear a proper kilt, so the wrap that is off to one side and the back works fine. 
 
Over top of that, I'd like a double wrapped swordbelt along the lines of this one here, probably black in color, or at least dark grey. The scabbard would rest on his left side (I say would be, as the scabbard doesn't necessarily need to be in the picture, as he usually just carries his primary sword & scabbard in hand). If you could fit a small pouch or two on the belt, that'd be great.
 
Speaking of weapons and belts, I'd like a chest harness/baldric for the remainder of them. On it, a short sword will be strapped across his back (hilt situated on the left side; I imagine that'll be the only part showing from a front shot, so not a real concern). Something along this line would work: pic. I like the offset straps as opposed to a crossed front type (like an X, I mean). You could even toss the small shoulder pad in too, if it fits the picture and you think it adds flavor. That's something I couldn't do on Soul Caliber III, so not sure how it'll look, but might be worth a shot. 
 
With the harness above in mind, I need to fit some other things in, but I'm going to leave the exact placements completely up to you, as I have no clue how they'll best fit in with the rest of whatever concept this whole idea brings to your mind. Basically, I need to fit in four pistol holsters (piratey flintlock type pistols, in keeping with the available fantasy technology). I have a reference pic with a couple of placements I like, if it helps. Whatever the specifics of what you come up with, I really like the idea of two sets of two together. Maybe one set somewhere at the waist/hip level, and one set somewhere along the back of that chest harness.
 
So that people have a clue as to what they are, if its possible (i.e. if you are willing to draw one), I'd like to have the pose with one of the pistols in hand. I imagine they might be a pain to draw, so this isn't completely necessary. If you do choose to, I simply ask that it doesn't have a flared barrel, and that you make the pistol more on the larger side than the smaller (I just can't handle tiny little guns, heh). 
 
With or without the pistol in one of his hands, I'd like his primary sword to be in hand. Traditionally, he's used a bastard sword most times (in conjunction with the short sword via Two Weapon Fighting), though in keeping with the fact he's a rogue, a thinner blade would work better than something overly broad (not rapier thin, though; simply a medium-slim, double-edged blade will do). Feel free to play with the hilt, guard, etc, although I prefer silvers to golds where that's concerned. The only real detail I would need on that is a blue gem worked into where the hilt guard and blade meet.
 
Alrighty, enough babbling about all that stuff he wears. That should cover it, and if not, I'm only an email or deviant note away.
 
I don't really have a pose in mind. Nor do I know what you prefer to work with here (performing an action of some sort, standing there looking pretty, crouching, etc), so if you come up with something that you'd like for this, please run it by me. 
 
Though I don't have a particular scene (and hence, no real background in mind), I do have one request along those lines, and if you can't or don't want to do it, please just let me know. I've noticed you have superimposed (I think that's the word) images (such as a close up of a face) in the background on some of your work. What I propose is to have something like that, with his cloaked/robed form being the image. To help with this, I have (yet another) pic that shows what it would more or less look like. The scarf actually turns into this upon command (semi-sentient intelligent "magic item"), covering him almost completely, save for his hands. I'm hoping this could work to show a duality of sorts (to those who know more about him, at any rate). 
 
If that's a real bother, just let me know. Lisa says put something "glowy" in the background (as you do kick-ass illuminations), so that could work too LOL
 
Whew, alright, I'm sure that's a lot to absorb (took me two evenings to write up, bleh), so I'll quit yammering about it now. Like I said before, if there's anything that you think wouldn't fit, or if you think of some detail that could work that I didn't think of, please run it by me. And if the whole thing seems like too much, don't be afraid to say so.
 
Get back to me with your thoughts and the particulars of payment and whatnot whenever you get the opportunity. Thank you very much for even considering this, I really appreciate it.
 
Mike