Hi Maneera! Thank you so much for your comments and suggestions.

I think you're absolutely right about the shorts - I need to push myself out of my comfort zone and wear them more. Skirts and dresses are easy for me, but I always feel frumpy in shorts. I think this is largely due to the fact that my casual selection is pretty much non existent and has been so neglected! I need some good polished tees/tanks to offset the more casual feel of the shorts I do have.

I love your vest idea! I'll have to keep my eyes out for something that feels me. A vest is lightweight layering which could definitely work in my climate.

I finally figured out that if something is DCO (dry clean only), I will never wear it casually because it is too *precious*. Now, virtually everything I buy can go in the washer at the very least in the Hand Wash or Delicate cycle. That has helped the cross-over issue a bit. My chambray shirt, Ts, moto vests, denim vest, and denim jacket help to dress down dressier pieces, as do footwear. But certain pieces are harder to dress down, and others are harder to dress up. Fabrication seems to make a big difference.