For a look that's classy and totally gasp-worthy, try teaming an olive wool double breasted blazer with charcoal wool dress pants. Dark brown leather loafers will give a dose of stylish nonchalance to an otherwise traditional look. So if you're searching for an outfit that's stylish but also feels entirely season-appropriate, this is it. If you often wonder how to dress as a gent in his twenties, this getup is a winning option.