Dress in a black wool shirt jacket and white chinos and you'll look truly dapper anywhere anytime. Finishing off with dark brown leather loafers is a guaranteed way to bring a bit of zing to your getup. When it comes to dressing for autumn, nothing beats a kick-ass outfit that transitions easily between seasons. Nice and age-appropriate for a gentleman in his 20s, an ensemble like this will help outdo any of your pals.