Penny Loafers are great for this time of year because they can look good with almost any outfit. These classic shoes that once seemed cliche to me, are now one of my favorite ways to dress up any outfit. Yes, when most think of this look it probably comes with the image of mid thigh length shorts, a tucked-in button up, and a sweater tied around your shoulders, and although this is a great look that I advise everyone to try at least once (you will feel like a Polo advertisement for the day), you can add them to more casual outfits for a new spin. Try them with a pair of khakis or chinos rolled up once or twice at the bottom of the leg, without socks, paired with your favorite shirt (this can be anything from a loose fitting tank, your favorite t-shirt, or button up). I often times find that generally changing shoes on an outift does wonders alone. Here are a couple pairs that I like.