Classic or Trendy? Walking the Style Line

Classic or Trendy? by girlseeksstyle! featuring black heels

I am generally drawn to more classic, timeless pieces but occasionally indulging in fun, spur-of-the-moment style spices up a closet. I always consider the lifespan of an item before purchasing--will I still think neon jellies are cute next year? Do I see myself donning full sparkling sequins a few months down the line? Sometimes trends can be tricky and maybe not worth the investment, depending on what works best for you. What's your take? How do you walk the line between "wear forever" and "wear for now?"