One of my favorite new pieces for Fall is undoubtedly the Sweatshirt Dress (I own #1 pictured above!). Incredibly comfortable and cozy while still looking quite put together. I pair mine with sandals while it is still warm and will move on to flats and sneakers and then booties with tights/leggings. There are some great options out there… some high end and very excitingly some really cute options for under $100!
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