It's always good to look one vs. the other. Trendy is for the teenyboppers, pretty is for anyone over that! Now there is a statement, try to define it when you dress, that's interesting. But I think when you see a good look you know it. Perhaps a really basic pant and dress shirt but with a fabulous shoe and belt. That's a good look for anyone over say 40, 50, 60!
Remember, fashions fade, style does not.