And ST09 Kirk went from cadet to Captain without even graduati--- <slap>
Re: Cadet uniforms, I think it was intended that Wesley's original outfit, with the red, yellow and blue horizontal accent stripes, was meant to be a uniform of SOME sort and not just something his mum pulled out of the closet. Likewise, during the original TNG run I was always thinking that his grey jumpsuit was a cadet's uniform and not an "acting Ensign" uniform, but he was wearing it at the same time as the not-Bolian in "Allegiance", so that may not hold weight.
Cadet uniforms ended up standardized as of TNG S5, and was refined in DS9 to replace the black with grey. This was in turn revised AGAIN to be more analogous to the FC uniform motif for their only appearance in "Valiant" (footage re-use in "WYLB" nonwithstanding). But in the not-likely-future of VOY "Endgame", a class of cadets had reverted to a slate of grey pajamas with black piping, suggesting that by THAT version of the 2390s cadets had to once again earn the right to wear primary colors.It's also worth pointing out that after TNG, all cadet uniforms also lost their year designators, that we could see anyway.
Mark