For a cool and casual outfit, dress in a grey long sleeve t-shirt and navy jeans — these two items work pretty good together. If you wish to effortlessly kick up this ensemble with footwear, complete your ensemble with black leather loafers. So as you can see, it's extremely easy to look dapper and stay snug when cooler weather arrives, all thanks to outfits like this. This one is a stylish yet mature outfit for maturing guys.