For a look that's nothing less than envy-worthy, try pairing a light blue double breasted blazer with dress pants. Inject some casualness into this look with a pair of tan leather derby shoes. As you can see here, it's extremely easy to look on-trend and stay toasty come chillier weather, thanks to this ensemble. As a 30-something Millennial man, you probably want to start dressing more maturely. That's when ensembles like this are a safe option.