Dress in a navy bomber jacket and a short sleeve shirt for comfort dressing with a twist. Finishing with a pair of navy and white canvas low top sneakers is a fail-safe way to add a touch of stylish casualness to this look. Can you see how extremely easy it is to look dapper and stay toasty come cooler days, all thanks to combinations like this? Wondering how to dress your age as you pass the big 5-0? This ensemble is a vivid example.