Booties and sweaters... That's pretty much my fall uniform on repeat right there if you haven't noticed. My Rag & Bone Newbury's paired with a chunky knit or a cardigan is the perfect casual, stylish, yet comfortable look. I am such a Gap girl - you can find some gems there, and they have very frequent sales (as in like every single day).
My secret is to pair something inexpensive from Gap or a similar store, with a designer or high quality accessory or two. My whole outfit, other than the bag and shoes is under $150, but you can't tell, can you?! I think a good leather purse and/or great boots really dress up and complete an outfit. Some of my favorite quality bag and shoe staples are below.