A hoodie and jeans are totally worth adding to your list of menswear essentials. When it comes to shoes, go for something on the smarter end of the spectrum and complete this outfit with black leather loafers. So as you can see, it's a sharp, not to mention season-appropriate, combination to keep in your transeasonal rotation. As you're progressing through your late 20s, you want to start dressing more professionally. If that's the case, outfits like this are a lifesaver.