Sunset,
Love your casual outfit. And I agree with you, when buying a jacket, the right fit is important. It's okay to pay a little more for them b/c you can wear them with so many different things... and they last for years... vs t-shirt or pants, etc.
Like you, I buy less expensive basics... love Arizona and Decree V-Neck shirts from JC Penny... for $2 to $3 a piece.
I spurge on shoes and jackets b/c to me, these are critical. Shoes for comfort and half-way decent looking (I know, they are not sexiest shoes, but better than wearing gym shoes and they are just as comfy as gym shoes). Jackets... well... they do so much for me.