I almost always grab a light jacket, because in central Illinois, the weather can change every 5 minutes. If I don't need to wear it, I can always tie the sleeves around my waist.

It's useful to think about habits, why we have them, and whether they serve us.

For clothing inspiration, I recommend The Vivienne Files, which has posts about clothing sets for different themes, weather conditions, etc. The author is very fond of layering garments to account for changes in weather. Plus the posts are just beautiful to look at.

For habits, consider goals_on_dw which covers things like making new habits and has a page of printables including habit trackers.