This combination of a shirt jacket and navy jeans is on the casual side yet it's also dapper and really stylish. If in doubt about what to wear when it comes to shoes, go with a pair of navy boat shoes. As you can see, it's very easy to look awesome and stay snug when colder weather hits, all thanks to combinations like this. Off-duty combos for middle-aged gents aren't actually that hard, as you can see.