The best season to wear aleather jacket Wellington is autumn. Autumn brings the perfect cool, crisp weather. The temperatures are just right for throwing a classic leather jacket over a T-shirt or a light sweater. A leather jacket in autumn can protect you from winds and is easy to layer. However, you can also wear it in spring, summer, and winter, but it depends on how you layer it. In spring, you can wear lighter and thinner leather jackets. In summer, evening or nighttime, and in winter, you will have to layer it with a heavy wool sweater.