Dress down for the day in this practical pairing of a military jacket and navy jeans. High top sneakers are a guaranteed way to add a touch of stylish nonchalance to your outfit. When you're having one of those dull autumn days, sometimes only a kick-ass outfit like this one can get you to face the outside world. Those who are dubious whether you can still sport modern casual looks as you slip into your 50s, you have your answer.