A lot of menswear and style blogs usually are in support of men wearing dress shoes more as it tends to portray elegance and a certain sartorial standard but that’s not my cup of tea, I have only one dress shoe and I’ve hardly worn it. I’m more of a casual dressed up shoe guy and one brand I’ve grown to love is Nanny State . This chic Winston Loafers retail for $67.99 and will sure complement loads of outfits in my closet.