You'll be surprised at how super easy it is for any guy to pull together a casual ensemble like this. Just a bomber jacket married with blue ripped jeans. Chelsea boots are a surefire way to inject a sense of polish into this look. As the weather starts getting warmer, it's time to shed those bulky winter clothes and opt for an outfit that's lighter, like this one here. This getup illustrates that as an over-40 gentleman, you have a wide array of dressing options.