I always struggle in late August/September for what to wear. While it is still officially summer, the colors tend to tone down and I never know what to wear. I tend to lean towards skinnies but sometimes I want to throw on a dress and that usually means black is my color go-to. My key requirements for transition dresses are either long sleeves or easy layering looks. I love pairing jackets with shift dresses but I also love long sleeve dresses that keep me a bit cozier. I also love the idea of a cotton maxi (love this one for $80) with a jean jacket. So easy and comfy too. I don’t like to spend a lot during these transitional months so here are some great ideas for under $100 each.