One of the classiest ways to style out such a hard-working menswear item as a grey blazer is to wear it with white dress pants. On the shoe front, this look pairs nicely with brown leather double monks. This outfit is a viable choice when it comes to a cool ensemble that will take you from summer to fall. As you're going from your 20s to your 30s, you probably want to start dressing like a grown-up. If that's the case, inspiration like this comes in very useful.