Is anyone else having the same issue I am? I wake up at 645 am everyday, walk out on my balcony and it feels like it's the middle of December. So I go and get dressed accordingly. Everything is great until 2pm when it now feels like the middle of July. I think many people are on my side when I say this season is extremely hard to dress for. But just to clarify, I am not at all complaining.
The good news about this bipolar weather is it allows us to transition slowly to the dark side. You can still wear mini skirts as long as you balance it with a fall/winter upper half. You can still wear leggings and a tank as long as you pair it with high top sneakers and a shirt tied around your waist. You can also still wear summer maxis, or short dresses with a leather jacket or sweater. It's really easy to incorporate spring and summer pieces into Fall and Winter if you use your imagination (or a stylist).
Having said that, I will take July afternoons in October all day, every day in Chicago.