STARTING FROM SCRATCH : sweat it.
please, try something without a college logo.
or, any logo.
think a color, or gray with an accent.
think slimmer fit, more like a sweater, more like a shirt,
and look to a higher gauge fabric than cotton,
something that might last you a few years.
then, let it mix with flannel pants,
and nothing else.
if you buy matching pants, you are reading the wrong blog.