I caught my running shoe trying to jump back into my shorts, tripped and fell. Scraped a knee and twisted it a little which was not cool as I was 11 1/2 miles from my car on a trail.
You might be surprised what is possible. I managed an hour and 5 minutes outdoors with only a ski cap and sneakers at 52 degrees F. 20 minutes at 49 (could have gone longer but had a commitment). Wind is the killer though. With wind it’s a dealbreaker.