I've done plaids, too, and I found that you must first discover what the fabric shape and form would look like without the design (plaid or stripes or print), and then adjust the design to match the values and hues that would be evident in a solid color fabric. In this work, I see all your dark blues and all your lighter grays as almost the same throughout the shirt, and so we receive few visual clues as to form. I realize that this is a small area on a small subject, and it may well be that you've done everything you can. Indeed, it does appear that you've darkened the far edge as it moved out of the light. I'm merely suggesting some possible areas for a second look. Think about how you'd have pushed the form (folds and wrinkles and such) in the shirt if it hadn't been plaid, then adjust the parts of the design to match the way the plain fabric would have been handled. By the way, as for the plaid pattern itself, I think you've done an excellent job. Don't fuss with the detail any further.
I do agree with Denise that the shoulders look slight, especially in proportion to the head size. Even with foreshortening, the shoulder closer to us seems pinched, and to almost disappear in its mass.
You mentioned the hair/haircut, but anatomically I see a larger problem in the size of the upper skull, even allowing for the age of the subject. He's certainly not an infant, with a proportionally large upper skull, yet in this guy, I see the eyes very much below the roughly "halfway" landmark that we'd expect to see. In fact, the top of his hair might well be as much as half the fullness of the hair that we now see. This will drop the "bangs" line down the forehead somewhat as well, and may address your uneasiness with the hairstyle.
I agree also that some work with the background will be helpful, to distinguish it in hue (perhaps complementary) and value (darker) from the subject. [That is certainly not a rule, just suggests itself here. Sometimes similarly hued and valued background and subject works out very well.] Once you alter the background (if you do), there will be additional considerations about how to have the edges meet between subject and background.
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