Why not consider pairing a shearling jacket with a blue denim shirt? Both items are super practical and will look awesome paired together. Brown leather work boots are the most effective way to add a confident kick to the outfit. Rest assured, this combination will keep you toasty as well as looking on-trend in this transeasonal weather. Those wondering how to pull off cool off-duty looks as you make your way through your 20s, you have your answer.