The Men’s Dress Shoe Dilemma

Honesty is the best policy, so I’ll start out by being honest. My first draft of the article you are reading bashed the square toed-shoe. I couldn’t come to terms with the fact that almost all men go to the store and purchase a pair. Men don’t care about the style of dress shoe they’re wearing? They don’t know the difference between a brogue and a loafer? Seriously,  it can’t be that hard, right?

A week or so later, I began to slowly comb through my words and go through the final editing stages before publishing. The pictures checked out, no grammatical errors, or fragmented sentences, et cetera. For the most part, everything seemed to be in line and ready to go. However, there was something that was holding me back from hitting the blue publish button on the side of the page. I had a sixth sense that something wasn’t right. I re-read the article a half a dozen times or so. Still, I couldn’t figure out what was wrong.

I decided to take a break from writing and run a few errands. I doubt you will want to hear about my ventures at the grocery store, so I’ll cut to the chase. One stop was at a major retail store and I was browsing through the shoe department. I am cordial with many of the associates and casually discussed my weekend and plans for the summer. After a few musing minutes, I broke free and spent some time looking over the new loafers that had just arrived. I was casually approached by a young man; I would say he was most likely around 21. “Hey, so sorry to interrupt, but how do these loafers look on me,” he asked politely. As I turned to face him, I was confronted by a sheepish gentlemen wearing what seemed like a suit made for an NBA player (this gent was maybe 5’9 165 pounds). He was swimming in fabric and could not have looked more uncomfortable. I kindly informed him that I thought they were OK and pointed him in the direction of  a more expensive Magnanni pair that I thought would suit him best.  He tried them on and immediately feel in love with them. We continued our discussion and I explained to him my passion for menswear and how I became involved with various on-going projects. He listened intently as I discussed, well honestly, educated him on the men’s dress shoe and the investment that they truly are. From there, we moved onto the suit he was wearing. It was in need of  a major re-construction. As a matter of fact, he needed to donate it to a local thrift store. If you’re going to buy a well crafted loafer from Magnanni, then you should be wearing a pair of pants that show them off. He had never been to a tailor nor did he understand that it was an important part of the suit process. Mid-way through our conversation I paused, and that’s when the light bulb came on. Here’s a young man, fresh out of college, entering the world for the 1st time. He had a job at a major accounting firm and was truly interested in finally growing up (throwing out his baggy sweat shirts, black socks, and basketball shoes). Problem was, he had no idea where to begin. He was lost, like a group of freshman on the way to a fraternity party. Dressing well had never been a priority in his life. This was what my article was missing; I had criticized without any knowledge or experience from the common man.

Why was it that I had become pessimistic and rude about those who have no interest in menswear? Was I naive to the fact that others didn’t care about the same things I did? Yes, menswear is losing it’s “taboo” label with major design houses like J.Crew bringing a new breed of fashionable men to the forefront. I think there is something bigger out there—an answer to this conundrum that we (in the menswear field) are finally coming to terms with.

It all comes down to education. Unfortunately, my father never explained to me the importance of dressing well. I never heard, “Here son, these are my wingtips and shoe trees. Take good care of them and make sure they’re shined and polished on a weekly basis.” Yes, he taught me everything there is to know about life and that is something that can never be replaced or duplicated. But, we as American men don’t have the ritual rights of passage into man-hood like others do in parts of the world. It’s a common custom in parts of Italy, France, Spain, and England for fathers to introduce their son’s into a world of sartorial excellence. I personally feels that we have lost this mentality in the States. Fortune 500 companies allow their employees to show up to work in a polo and slacks. Seriously, you resemble a 5th grade catholic school student.

Don’t get me wrong, I love what the current menswear magazines are doing to push both the classic and newcomers to a mainstream audience. Not only are they offering every price point for a modern day consumer, but they are pushing the idea of dressing and living well to new heights. What they are neglecting to include in the dialogue is the formal education of a modern gentleman. I set out this month to start a series of lessons that dive deep into the world of menswear. This week I am starting off with what I feel is the most important part of a man’s wardrobe, the dress shoe. You can tell a lot about a man by his dress shoes. If taken care of properly, they age perfectly and will only look better.

This week we teamed up with one of our favorite men’s shoe stores in NYC, Leffot, to bring you a first-class education on the men’s dress shoe. Steve from Leffot adds, “In today’s economic climate competition in business is fierce. Any small advantage you can create for yourself is a plus. Men notice how other guys dress, they pay attention to the suit, watch, and of course, your shoes. You only have one chance to make a first impression.” Class is now in session. Let’s get started with the basic in any mans wardrobe, the oxford.

Alfred Sargent Hand-grade


The oxford is a well known dress shoe. Characterized by its closed lacing design, the oxford has truly become the “go-to” men’s dress shoe. If you’re new to the game, which I hope most of you are, the shoe you most likely buy without knowing is the oxford. The tongue of the shoe (the piece that rest on the top of your foot) it cut separately from the vamp (the front part of the shoe that allows the shoe to fit onto your foot). Oxford’s were originally made from leather, but designers are now creating them in different materials (suede and canvas). Many cobblers will also add a “cap-toe” design to the lower end of the shoe. Above we highlight the Moore AS53, a shoe from the well known cobbler, Alfred Sargent. It’s from their 2011 collection with Leffot, which may not be the “newest” collection, but again, it’s about timeless style with your dress shoe.

Edward Greene Wells


Next up, the Derby (also known as the blucher or bucks). It’s less formal and can be worn for any occasion. Notice the difference in the lacing (compared to the oxford). The open lacing allows more of a relaxed fit on your feet. The facings for the laces themselves are sewn on-top of shoe (the vamp). Like the oxford, designers are using multiple materials to add splashes of creativity and color. Derbies are often worn in the summer, usually with a canvas style fabric. Here we highlight Edward Green’s work, the “Wells.” Made of classic dark oak calf-skin, the Wells combines an effortless style with exquisite tones of color.  This might just be the best shoe in your closet my friends.

Pierre Corthay’s Vendome


To some it’s known as the “full brogue.” However, many state-side folk gave it the “wing-tip” name for the flying W pattern on the front of the shoe. The oxford and brogue (wing-tip) shoe are almost exactly identical. The only substantial difference is the pattern on the toe. Wing-tips get their nickname from the flying “W” pattern that extends across the entire shoe. Personally, the wing-tip is my favorite shoe. You can dress them up with a pair of straight-fitted jeans for a night out or pair them with your favorite trousers for the office. Leffot carries these, designed and built by the master craftsmen behind the family owned and operated Pierre Corthay.

We’ve covered the three basic men’s dress shoes; the oxford, derby, and brogue. The next step, which to be quite honest is the most important, is the care of your shoes. It goes without saying that you MUST understand how to properly take care of your shoes. They will last a lifetime if you take these important steps.

Shoe Trees

Seriously, don’t be lazy. It takes under a minute to insert shoe trees into the shoes themselves. They keep the shape and integrity of the shoe in mint condition. They also help work out any kinks in the leather from day-to-day wear.

Shoe Horns

Shoe horns are an under-rated part of any shoe care kit. Shoe horns are used to help slide your heels into your shoes without causing any damage to the back of your dress shoe. We really like these from Abbeyhorn. Made from oxen horn, each pair is uniquely crafted and patterned.

Shoe care Kit

Shining shoes is an art form (just ask the gents at Leffot). Shoe care kits are an option, however, when it comes to shining your shoes, we recommend someone with a bit more knowledge at first. Personally, I take them to my cobbler here in Cincinnati. He’s a 20 year-old student who honestly turns my shoes back into the condition they were in when I bought them. It’s like Christmas when I pick them up (there has been a few occasions where I honestly thought he traded mine out for a new pair). Find a cobbler in your town and spend time discussing your pair and what kind of shine you are looking for. However, if you’re down for the challenge, order a shoe care kit and teach yourself how to master the perfect shine. It’s important that you start in a small area of your shoe (the back heel) when you’re first learning to shine. Learn the tricks of the trade and be patient! Rushing can cause staining that will ruin your shoes.

Let us know if you have any questions for A&H Magazine. We realize that this can be a big step for many. Remember, we support the longevity of the product. A hand-crafted pair of dress shoes can be expensive, but your paying for the lifetime not the moment.

Special thanks to Steve and our friends over at Leffot for their collaboration and images for this piece. Their store and selection is absolutely amazing. They are the Rembrandt and Picasso of the modern day shoe world.



Christopher Dam

Christopher Dam is a senior writer/photographer with A&H Magazine