Jackson is adorable in his longer hair, and it would probably be nice for added warmth in winter. However, I do love his clean, crisp shorter look and it is much better suited for warm weather activities.
I took my boys to the park after a big rain yesterday. Although we stuck to the pavement most of the time, they were wet and muddy by the end of the hour. I spent an hour and a half cleaning them up when we got home.