For a laid-back and cool outfit, go for a sweatshirt and black chinos — these pieces fit really great together. Let your styling credentials really shine by finishing off this ensemble with a pair of low top sneakers. While it can be a bit challenging to look stylish in cold temperatures, it's outfits like this that prove it's totally possible. As a 30-something Millennial guy, you want to start dressing like an adult man. If that's the case, ensembles like this are a surefire option.