I’ve said it before and I’ll say it again, for me, fashion has to be comfortable and it has to be easy. If you’re comfortable with what you’re wearing, it will give you an added boost of confidence. If it’s simple to pull off, you’re more apt to follow through. For me, this outfit is as close to wearing pajamas in public as you can get. When it comes to style-conscious comfort, you can’t beat a drawstring short. Drawstring shorts were a hot trend this past Spring/Summer and the drawstring look is definitely transitioning into Fall/Winter with jogger pants in all fabrics, textures, and colors. (I’m thinking about getting a pair from The Publish Shop—see here). Pair the drawstring shorts with a short-sleeve button up and a broken-in pair of leather penny loafers and you have yourself a casual outfit any man of style would be proud of.