I’ve had a typical relationship with dress shoes my whole life. As a youth, I dreaded wearing those stiff black shoes to church. I couldn’t wait to get home and change into my sneakers so I could go outside and have fun. I also did a report on shoes once in elementary school. Some of the fun facts I learned were:

• In 1790, the first leather shoe with holes for laces was invented.
• The Italian Renaissance inspired Italian designer Ferragamo to invent the platform shoe in 1937.
• Economic sanctions in Italy in the 1940s forced Ferragamo to design the wedge shoe since he couldn’t use metal in the heels.
• Your feet flatten as you age, so your shoe size can increase up to 1 and a half sizes or more as you get older.

As a teen, I occasionally donned those dreaded dress shoes for formal dances and special occasions. I envied the girls at the dance who would take off their shoes. It wasn’t until shortly after college when my roommate got married that I was introduced to a whole new way to dress up in a suit. Instead of renting the worst black dress shoes known to man from the local tuxedo rental store, Josh suggested we wear sneakers. Not just any sneakers, but mens sneakers you can wear with suits.
The white mens leather sneakers paired with our grey suits actually looked pretty sharp. I was surprised. And despite wearing them all day when you take into account the two-hour photo shoot, the wedding ceremony itself and the reception, I never felt like taking them off. I couldn’t believe it. Finally, a shoe I can wear and still be dressed up. After the wedding, though, those shoes sat in my closet as I was unsure if I could really wear them to work. After all, at the wedding I wasn’t alone in my sneaker wearing. The other 5 groomsmen and the groom himself were also sporting the look, so anything goes. After some research and paying closer attention to my colleagues at the design firm, I noticed that some men were wearing these hybrid shoes or crossover mens sneakers. Here is what I learned about these shoes and how to successfully wear them to work.

• Sneakers. There are actually a few variations on the sneaker. They go by names such as low cut sneakers, leather sneakers and minimalist sneakers. They come in white like I wore to Josh’s wedding but also in a small range of neutral colors such as blue, black, brown and tan. Suede slip on sneakers come in a little brighter variety of colors such as greens, blues, oranges and reds.
• Leather Derby Shoes. These look more like a dress shoe but are still a sneaker sole with a stitched dress shoe upper. All the dress of a high quality leather dress shoe with the comfort of a tennis shoe sole. These leather derby shoes come in fairly standard neutral colors such as blacks and browns and oxblood.

How To Wear This Look
A nicely tailored and fitted suit works best with this look. And of course, high quality Italian leather makes the shoes match the dressiness of your suit. If you live on the coast, you’ll notice that most men wear their suit sans socks. This is especially true of the suede slip ons and minimalist sneakers but less true for the leather derby shoes. Pay close attention to personal grooming as well. This sleek and youthful look necessitates a similar hair cut and style. Most of the men in my office who wear this look are clean shaven.
I love my new look so much that I don’t mind dressing up for work every day. I even occasionally wear a dressier look out to dinner and dates now that I have my comfortable leather derby shoes as an alternative to uptight dress shoes. Considering that 50% of women say that a man’s shoes reflect his personality, I’m really pleased about what my shoes say about me. My shoes say that I like high quality but I’m not uptight. My shoes say modern. My shoes say class. I’m confident my look will attract a woman who appreciates the same.