Rock a tobacco shearling jacket with a navy and white plaid long sleeve shirt to feel instantly confident in yourself and look cool and relaxed. For something more on the classy end to complete this ensemble, complement this ensemble with a pair of brown leather casual boots. Piecing together a kick-ass ensemble can be a bit difficult at times on its own. Enter cold temps into the equation, and the whole thing becomes even more difficult. Luckily, this here is your winter inspo. And if we're talking dressing ideas for 30-something guys, this outfit is perfect.