A black v-neck sweater and jeans are a good combo to have in your day-to-day off-duty lineup. Want to tone it down on the shoe front? Add black and white canvas high top sneakers to the mix for the day. As you can see, it's extremely easy to look dapper and stay toasty when cooler weather hits, thanks to this outfit. Guys wondering how to dress with style and look good as you drift through your 20s, you have your answer.