Down to the shoes, instead of going sockless in my boat shoes or tan loafers (which I've been loving to do when the weather permits), I went with my darker Tod's loafers. They aren't too chunky, so they don't clash with the more summery vibe, but they are a little sturdier and, more importantly, fit best with thicker socks. Once again, an item I wouldn't normally be incorporating into a 'summer' outfit, but that works perfectly in this situation.
I topped it all off with my lightweight Uniqlo blazer. I probably could have gotten away with wearing a wool jacket, but it's not cold here, per se, just a bit chilly in the shade and when the lakefront breeze kicks up.
Long story short, it's important to consider both style and functionality when dressing for the day. As tempting as it was to wake up and go all-out summer with my attire, it would have left me uncomfortable and chilly, and honestly would probably have kept me inside most of the day. Instead, with a few quick substitutions I managed to stay fly and warm. But really, Chicago, where is summer?
Cotton/Linen Blazer by Uniqlo
OCBD by Frank and Oak
Tie and Tie Clip by The Tie Bar
Belt by Levi's
Chinos and Socks by J.Crew Factory
Shoes by Tod's (via eBay)