Consider pairing a black and white varsity jacket with black chinos to achieve an incredibly sharp and current casual outfit. Rounding off with a pair of brown leather chelsea boots is a surefire way to introduce a bit of zing to your look. This getup is a good choice when it comes to picking out a well-coordinated ensemble for unpredictable fall weather. This combo shows that dressing stylishly as an over-40 man is quite manageable.