Surprisingly, one of the things guys have the hardest time with is their intentional, casual style. A sportcoat with some boots will always look great, but sometimes it can be a little too classic, like when heading to a music show and grabbing drinks with your friends. For a more casual, street style outfit that is super easy to put together, opt for a dark color palette. The henley is a smarter alternative to a regular t-shirt because of the visual texture it provides to the otherwise very minimalist outfit.
Don’t fear mixing blacks and browns: when done thoughtfully, like with the boots and watch, it’s clear you know what you’re doing.