If you're searching for a street style yet seriously stylish ensemble, consider pairing a blue shearling jacket with light blue ripped jeans. Does this ensemble feel too perfect? Invite a pair of work boots to change things up a bit. Keep this ensemble ready to go when spring arrives, and rest assured, you'll save time racking your brain for an ensemble on more than one morning. Relaxed ensembles for stylish 30-something Millennial guys aren't actually that hard, as you see.