I find it interesting that you crave "fun". Perhaps you should listen to your inner voice.
Earlier in my life I have sometimes kind of forced myself into a very classic and straight style. But the fun has been lacking. With time, I have realized that I NEED a little playfulness. Interestingly, when wearing items that are not strict classic but very "me", I often get compliments, perhaps because then my outfit is a reflection of my personality and I look "authentic".
If you happen to look good in orange and love the colour, by all means buy that top, and don't be afraid to wear it repeatedly. Of course, you risk to receive some compliments, but that's a risk that's worth to take.