This combination of a tan shearling jacket and sweatpants looks pulled together and immediately makes you look cool. Finishing with a pair of olive high top sneakers is an easy way to infuse a sense of stylish nonchalance into this ensemble. When it comes to dressing for transitional weather, nothing beats a cool outfit that will keep you cozy and looking your best. If you're often not sure how to dress in your late 20s, this getup is a practical illustration.