On the positive side, it is remarkable that the Princess is still able to wear outfits from 25-30 years ago, or even longer! Not many of us could say the same thing! And kudos also to her for being practical and recycling.
Not that she would likely take anyone's advice on clothing, but if I were advising her I'd have two suggestions. First, the Princess seems to favor bold prints and shapes which don't translate well from one season to the next, much less from one decade to the next. If she wore simpler classic styles, her clothing would not seem so cringe-worthy when they appeared again.
And second, she tends to wear the entire same outfit - right down to the same gloves or jewelry. I'd advise her to break up her items and pair them differently the second - or fifth time. Diana was very good at that, on the rare occasions that she herself recycled.