I'm good at riding in a wide range of conditions, but enjoy 56 - 70f the most. Above 56f, I can wear riding shorts alone, below this level, I wear tights. Above 70f in the Midwest usually includes high humidity, so staying cool can be an issue.
This year Chicago had a warm summer. I completed two long distance rides on the two hottest days of the year. The first 94f day was a metric 100. I was training with an younger Ironman athlete. It was a midday ride and the winds were howling above 15 mph. The second windy 94f day I completed an imperial century, but I started that day at 7am.
I’ll also ride during the winter months. I’ll select sunny and dry days and will ride down to about 25f. I’ll use an alpine ski helmet and a mix of cycling and skiing clothing to stay warm.
Hot weather requires careful hydration and cold weather requires the right clothing.
