For a classic and casual ensemble, consider wearing a brown waistcoat and jeans — these two pieces work really well together. A trendy pair of dark green canvas low top sneakers is the simplest way to infuse a dash of stylish casualness into this ensemble. So as you can see, it's very easy to look awesome and stay toasty when colder weather hits, thanks to this outfit. A reliable option outfit appropriate for over-40 gents who prefer casual clothing.