You'll be surprised at how easy it is for any gent to get dressed this way. Just a dark green military jacket matched with a crew-neck t-shirt. Finishing with a pair of grey athletic shoes is the most effective way to infuse a touch of stylish casualness into this look. When leaves turn yellow and red and fall sets in, you'll love this getup as your go-to for transeasonal weather. This outfit proves that after forty your sartorial options are looking good.