PS request: "How do I take a grey knit turtleneck sweater I've had for years and make it look semi-chic again? Is it possible or is it time to let it go?"
Well, if it's in good shape and the only issue is that you just are looking for a new fresh way to pull it off, then by all means, keep it. If, however, when you put it on, you just feel "meh," donate. Let's say the first scenario is the one we're going with.
If that's the case, don't overthink it. Sometimes the right accessories can change everything:
If the heel scares you: go with a chunky or stacked version that hits below three inches. If that still freaks you out, this would look perfect with a brown riding boot.
If the skinny jean makes you cringe: go with a bootcut or all-out in an on-trend flare leg jean. Or, you could go with a boyfriend jean that's distressed and pair it with a flat sneaker (or wedge sneaker) and go weekend-casual.