Rock a shirt jacket with black ripped skinny jeans, if you want to dress for comfort without looking like a hobo to look dapper. Finishing with a pair of tobacco work boots is a guaranteed way to introduce a more relaxed touch to your ensemble. So if you're hunting for an outfit that's stylish but also feels entirely season-appropriate, this one fits the bill. This outfit illustrates how to dress fashionably and look good as you go through your 20s.