Dapper up in a light blue chambray dress shirt and olive dress pants. On the fence about how to finish? Add dark brown leather casual boots to the equation for a more casual spin. While it can be a bit of a challenge to stay on-trend in uncomfortably cold temperatures, it's ensembles like this that prove it's actually possible. Wondering how your styling arsenal should look as you step into your 30s? This combo is a great illustration.