Go for a simple but neat and relaxed option by opting for a navy plaid long sleeve shirt and a white crew-neck t-shirt. Take a classic approach with footwear and add a pair of burgundy leather casual boots to your outfit. Picking out a pulled together combination can be a bit of a challenge on its own. Enter uncomfortably cold temps into the equation, and the whole thing becomes even more difficult. No worries, this here is your wintry inspo. This combo should erase any doubts you had about wearing casual clothes as a gentleman in his 30s.