If you gravitate towards off-duty style, why not wear this combo of a black shearling jacket and charcoal sweatpants? Opt for white leather low top sneakers and the whole ensemble will come together brilliantly. While dressing for wintertime can be a bit of a juggling act, it's outfits like this that make you feel inspired. Those who wonder how to rock cool casual style well into your 30s, this ensemble should answer your question.