A good pair of shoes on a man can be a deal breaker. When I first moved to the Midwest from New York one of the first judgemental and superficial things I noticed were these hybrid men dress shoes. Half loafer and half sneaker, they may even have laces, and the owner was most likely not wearing them because of orthopedic issues. These shoes are bad. I used to work in fundraising which for whatever reason is a female dominated workplace. A coworker once said he was looking for a new pair of dress shoes and showed another female colleague and myself these rubber disasters. We told him we were doing him and his girlfriend a favor, and no way could he buys those shoes. I am sorry people, but they are bad.
There are so many great, simple and comfortable men's shoe options. These cannot be an answer. And, in Chicago many people have to commute in boots, so if you get to your workplace and then put on this geriatric cheesiness I don't know what to say!
Enter the Oak Street Bootmaker. This is a wonderful family-owned Chicago men's shoemaker. They are not bargain basement prices, but a good pair of shoes is well worth their money, especially if you have a good cobbler. If not - find one, they will become a good friend. I have a pair of black flats that should have been put to rest years ago that I keep taking back to the cobbler and he resurrects them to my amazement every time. Back to Oak Street Bootmaker - the founder carried on this business from his father and all of the shoes are made in the USA. "The highest standards of production are employed to yield shoes that are as durable as they are comfortable. Each pair makes use of replaceable outsoles, a feature normally reserved for formal footwear, to ensure a lifetime of wear."
They are not bad to look at too. All-American and classic, they appeal to a wide range of tastes, ages, and interests.