Typically, people suggest go light during summer and dark during fall/winter. HOWEVER, it all depends on your hair type. If your hair is dry or damaged you should actually go light (but not too light) during fall/winter and darker during summer bc the sun and weather works better with your hair that way. As for a haircut: Since I want to keep my hair long, I usually tell my hairstylist to cut just enough so my hair is healthy... sometimes that means a little off the ends, sometimes it means 2 inches! Personally, I think there are way too many factors to consider: like height, skintone, bodyshape, facial structure, wardrobe, career, etc... These are all factors you should really consider. TO ME, A haircut is SO personal, it's hard to really advise others.