The Do’s and Don’ts of dress shoes are not as easily realized as one might think. And it greatly depends on your idea of the rules. Rules from 100 years ago are not the same as 50 years ago, which are not the same today. The term ‘no brown in town’ couldn’t be further from the reality in most cities outside of the borough of Mayfair, London. Yet, 50 years ago, that was a strict rule.

Gone are the days when rules dictate style choice. Although, probably needed more so now than ever. We went from one extreme to the other. A system whereby there were rules for everything to a new system where it is trying to break the rules at every corner. And now we just have a free-for-all of style that in the end creates some pretty bad style IMHO. And the shoes, well, as that is my forte, I will stick with the simple education on that. So, let’s look at the ultimate ‘Do’s and Don’ts’ of dress shoes.

Square Toe Shoes

In my very humble opinion, there is nothing more atrocious than a square-toed shoe. The brief period in which they were all of the rage in the shoe industry was a very sad, yet thankfully short time period. Steve Madden and Kenneth Cole plagued the shelves of mediocre shoe stores and the guys who thought they were the coolest thing ever also plagued the same stores. Thankfully, some smart shoemakers updated the square toe to a chisel last and the square toe vanished as quickly as it appeared.

What is funny to me though is when people refer to a chisel last as a square toe. I cannot for the life of me understand how they mix the two, with the only valid excuse being a lack of education on the proper terminology: chisel shape shoes. These same guys are the ones that only wear bulbous round toes and think that an almond-shaped last is ‘pointy.’ We will get to them below.

The square was horrible as a square by definition is the same width no matter which way you turn it. And that was the problem. No feet look like that, and having a spatula on your foot is not attractive. So, for me, the biggest ‘Don’t’ is to wear a pair of actual square-toed shoes. But a chisel last, on the other hand, is a big ‘Do’. Chisel lasts have become very popular in recent times and for good reason. An elegant chisel last is a serious dress style that greatly accompanies many various looks, most importantly one involving dress trousers.

Excessively Pointy Shoes

I feel like most people don’t know what a ‘point’ is. So many attribute pointy shoes to anything that does not look like a circle toe. I recently had a 2-star review in my shop from a person who walked in apparently and left without talking to us, claiming the style was too dandy with all of the “pointy shoes”. I found that funny as I hate pointy shoes and none of the shoes I make are, in fact, ‘pointy’. Not to mention getting a 2-star review because someone simply does not like the style of the product of the shop they randomly walked into. But here were are in the digital world where anyone can spew their feelings online, such as I am doing now 😉 enough of that quick rant!

Real pointy shoes, like the one above, are an extreme that is not only inelegant but on the verge of just downright vulgar. They are wrong on so many levels, mainly the one that has to do with walking properly as one can only imagine the awkward steps you have to take to maintain not destroying those points! You should never be able to kill a small insect in a corner with your shoes. That is simply not what they are made or designed for. But truly pointy shoes can do just that. And showing off that look should be avoided at all costs.

What you should wear are elegantly rounded toes, such as shoes made on almond-shaped lasts. These are the lasts that have a nice asymmetric shape to them that highlights the curvature of the feet but in an elegant manner. What such last is the Anthony Delos shoe below. It has a well-balanced last, with a nice elegantly round toe neither being too pointy nor too round. Balance is key in dress shoes and a super-pointed toe does not have any balance.

Overly Long Shoes

Elongation can be a hard thing to balance and the difference between just right and too long can be millimeters. For example, the pair above, by Finsbury, is a nice shape but it is just a bit too long. That length will cause a lot of upward toe spring which, for me, is just downright unattractive. Long shoes’ toes will always point upward as the last is not actually balanced properly. The toe is simply too long from where the ball of the foot lays. And where your toes fall way short of the tip, you get the upward toe and a lot of creasing in the cap.

While the Finsbury is just a touch over the top, you will find far more elongated ones on brands like Jeffrey West, John Fluevog, and for some reason, many obscure French brands that really make some long lasts that just don’t sit right. Elongation, like square and like pointy is simply another extreme that can be overly abused. But when done right, a touch of elongation can be very elegant and help to balance one’s body, in the instance of a tall guy with small feet.

The JM Weston loafer below for many would be considered ‘long,’ but in reality, they did a great job balancing that last and making an elegantly elongated loafer. And that is not always easy. In fact, doing elongation correctly is tricky. Because it is not just the length that you have to think about but the proportions of the width to the length. The Crockett & Jones loafers below have a very subtle elongation to them. Just the right amount to tricky even the round-toe-snobs.

Overly Round Toes For “Dress Shoes”

The foot is not shaped like a circle or a lump. Our feet are asymmetric and therefore lasts that better suit them are shaped similar to how our feet are. Some feet have their own special shapes but that is another story for another post. The fact of the matter is that anything too round is not dressy. It is not elegant. It is safe and it is boring. It is without elegance and therefore cannot be considered ‘dressy.’ Dress shoes must be elegant as that was the point of their being.

Think of your average Ecco or Rockport shoe. Those are not dress shoes, no matter how they spin it to you. They are shoes with ‘dress shoe’ designs but are not true dress shoes. They are not sleek and no matter what anyone tells you they do not look good underneath a suit. Sorry, but that is the truth. They might be comfortable but that does not equate to being a dress shoe.

A round-toe shoe does not have to be overly round. There are many classic lasts that are elegantly round, not fancy nor pointy, or ostentatious. Think of the 379 or 363 lasts by Crockett & Jones (see them below). They are both very elegant and classic round lasts. With a touch of elongation and the right proportions, a classicly round last can stand with the best of them. But when there is no elongation whatsoever then what you get is a clumpy-looking shape that simply does not sit well underneath anything besides jeans.

Shoes With Decorations

Dress shoes should not have metal spikes on them. Period. A buckle and a bit are acceptable forms of metal elegance but spikey bits and little metal balls all over the place are simply not worthy of being labeled a dress shoe and in no realm could they be considered elegant. Trying so hard to look cool only means you are missing the mark by a long shot. And any kind of fluffy decoration on your dress models is only going to look tasteless. On your casual shoes is another story. I still do not condone it but that, again, is for another post.

The reason why formal shoes are the ones that are the plainest is that elegance should be discreet in reality. The more simple you look the more elegant you appear. Just think of James Bond. You never see him wearing anything extravagant. It is always clean, classic, and simple. And he is often considered a style icon, even being a fictional character.

Anything that screams ‘look at me’ is just something you want to avoid, at least in terms of additives to your shoes. Wearing colorful shoes in the Summer time would constitute a ‘place and time’. Metal spikes or fluffy decorations have no place and time. It is only to call attention. Nothing more, nothing less.

While I could probably write a million more do’s and don’ts about dress shoes, these are the main ones that I think help one stay on track to wearing simple, classic, and elegant dress shoes. The basic rule is that any extreme is not great when it comes to being elegant and wearing nice dress shoes. You can play on the boundaries of extreme, but crossing that line will always lead to a big ‘DON’T’!