Corporate Style: Part 2 – The Shoes

In my last post, I mentioned that the business wardrobe has two anchors, suits and shoes. Suits are like Chris Bosh; important but nonetheless subtly overrated. Shoes on the other hand are like Manu Ginobli; people understand their importance at some level and yet they are highly underrated.

You will need a minimum of two pairs of shoes. There are a number of reasons for this, both practical and stylistic. First, it is extremely hard on a pair of shoes to wear them on back-to-back days. Some time apart from your feet in shoe trees are integral for them to last and stay looking their best. The second is that you will need a pair in black and a pair in dark brown. A running theme in dressing for business is trending towards dark items of clothing as dark clothing (other than with dress shirts) connotes formality. Thus, one’s first few pairs of brown shoes should be dark brown and not some of the lighter shades that are often available. In addition, these first two pair of dress shoes ought to be lace-ups as they are far more versatile than loafers. This versatility stems from their ability to be dressed-up while still looking cool with a pair of jeans on the weekend. Finally, shoes are the one item of clothing that is difficult to take short-cuts with in terms of cost. There is an incredible difference between cheap shoes and nice shoes and these tend to be readily obvious to just about anyone. Many women even suggest that shoes provide a barometer for them in terms of determining a man’s socioeconomic status. In the same way that fit is the first thing that people notice about suits, quality is the first with shoes and thus is important to buy, at the very least, one pair of good black shoes. Finally, under no circumstances should you purchase square-toed shoes. There was a brief time almost a decade ago where this style had a moment. However, one should never strive to be trendy in one’s business footwear; it is far better to buy a versatile and traditional pair of dress shoes with a rounded toe.


In order to buy dress shoes, it is important to understand a little about the elements that make up these types of shoes.

First, there are two primary types of shoes in the business world: lace-ups and loafers. Lace-ups. as the name would suggest, have laces, while loafers do not. Lace-up shoes are seen as more formal. A rule of thumb that I use to decide which type of shoe to wear is that when I wear a tie, I gravitate to lace-ups. If I’m wearing my dress shirt with an open collar, I might substitute in a pair of loafers given the slightly more casual tone of my outfit However, depending on the formality of your workplace, this may not be of high importance. As an additional personal preference, I tend to prefer my loafers to be brown given that loafers are less formal shoes and brown is seen as a less formal but nonetheless richer colour than black. A common loafer in the corporate world, at least in North America, is the tassel loafer, which has a small tassel at the front (pictured below at left). The company most famous for these types of shoes is Alden, an American firm. Another common corporate loafer is the penny loafer, which has two small strips of leather at the front in which Ivy-League students once place a penny for good luck, hence the name (pictured below at right). The most famous maker of penny loafers is Bass, who still sell them under the nickname “Weejuns”, a mis-enunciation of the name “Norwegian”. Finally, the moccasin type of loafer was made famous by the Italian company Gucci and often sports a decorative metal piece at the front that resembles (and is referred to as) a horsebit. All of these loafers can be acceptable in a business environment, particularly if they are in a dark colour. Somewhere between the loafer and the lace-up lies the monkstrap which can be seen below in the middle. While not seen to be as formal as a lace-up, they are nonetheless more generally acceptable than loafers and are suitable in many business environments. However, the most versatile type of shoe remains the lace-up.


Moving on, the sole of the shoe can be attached to the upper in two ways: via welts or via glue. Higher quality shoes are welted while lower quality shoes are glued. It is highly recommended that you purchase welted shoes. While they will be more expensive initially, they will last infinitely longer. From my own personal experience, I have two pairs of welted shoes that I purchased over five years ago and have worn regularly that still look nearly brand new (other than some wear to the soles which require replacement in even the best shoes every so often); I also have a pair of glued shoes I’ve owned for two that, while beautiful when I bought them, are falling apart. A cobbler will be very hard-pressed to do anything with glued shoes other than throw them in the garbage, while they can most definitely resole and heel welted shoes. There are two primary methods in which welted shoes are made: either with Goodyear or Blake welts (these are named after the men who invented these methods of constructing shoes). Most bench-made (essentially another way of saying “handmade”) English shoes are Goodyear welted, while Italian manufacturers often use Blake welts; there is a case to be made that Goodyear is superior to Blake, but it is largely irrelevant. All of the shoes pictured in this article are Goodyear welted, evidenced by the channeled stitching on the soles. Both methods of shoe construction will stand the test of time.

Another suggestion would be to steer clear of the shoes sold by most “fashion brands” as they are generally a terrible investment. The quality of shoes from such brands as Hugo Boss and Prada are generally very mediocre compared to the price charged. However, some brands, most notably Ralph Lauren, farm out the construction and design of their shoes to top shoe makers such as Crockett & Jones and Edward Green and thus can be fantastic buys.


The next element of a lace-up dress shoe is the means by which the laces are attached to the shoe. Once again, there are two styles: open or closed lacing. Closed lacing is the more formal of the two and is pictured above at left. The term ‘open lacing’ indicates that the laces are attached via two flaps of leather that allow more flexibility (and thus generally more comfort) for the wearer’s feet (pictured on the right). Personally, I tend to prefer the more sleek appearance of closed lace shoes and I would recommend this style if you are only buying one pair given that it is suitable for even the most formal of occasions. However, so long as you have one pair of closed lace shoes in black, the rest of your shoes could be open laced construction and you would get neither second glances nor criticism. The choice between open and closed lacing is a matter of personal taste to a large degree.

An additional element to any pair of shoes is the existence or lack thereof of any decorative elements. The most common type of shoe decoration in the corporate world, at least in Great Britain and Canada, is the captoe which can be seen on the first shoe pictured in this article on the left. Captoe shoes have the toe stitched onto the end of the shoe via a stitch running across the top of the shoe. They are entirely appropriate in nearly any environment and I would certainly recommend them to anyone starting their shoe collection. Other shoes have holes punched in them in decorative patterns and are referred to as “brogues”. These shoes are less formal than captoes but nonetheless are generally acceptable in any business environment. An example of a brogue can be seen below on the left. In the United States, a particular pattern of brogue, called the “wingtip” is probably the most common style of dress shoe (and can be seen below on the right). Finally, certain high-end shoe manufacturers offer shoes that are made from a single piece of leather and are completely devoid of visible stitches on the upper. These are called “whole cuts” and are both distinctive and relatively formal while still being acceptable in a business context. Overall, versatility should be the goal when initially purchasing dress shoes and thus I would recommend starting with a captoe oxford in black. From there, feel free to explore the world of brogued shoes and whole cuts.


The sole of a dress shoe can be leather, rubber or some combination of the two; all of the shoes pictured in this article have leather soles. It is highly preferable that you invest in a leather-soled dress shoe as they are universally acceptable and if there one thing that One Guy’s Style Blog stresses for those starting a business wardrobe, it is versatility. Furthermore, they are far more elegant and tasteful than their rubber counterparts and often no less comfortable. They can, however, wear out faster and thus certain measures should be taken to protect them. Upon initial purchase, one should have a small piece of metal or plastic called a toe tap attached to the front of the sole by a cobbler. This procedure will likely cost in the neighbourhood of $10 and will greatly extend the life of the sole. Secondly, one should be sure to wipe off sand and salt that may build up on the sole immediately upon reaching one’s destination. Thirdly, I would suggest wearing rubber oversoles in the winter; not only are these helpful for grip, but they will also prevent exposure to the wet and salt.

Finally, it is important to purchase the right size of shoe. Shoes are sized not only for length but also for width and both are equally as important. An ill-fitting shoe will wear faster, cause blisters and lead to discomfort. If you buy your shoes to last, than each of these issues run completely contrary to your purpose.

I have thrown a great deal of information at you in the preceding paragraphs and therefore I thought I would attempt to simplify things by suggesting some manufacturers that make high-quality shoes at a relatively decent price. First, widely available are shoes from American maker Allen-Edmonds (www.allenedmonds.com). Allen-Edmonds shoes are extremely well-made, Goodyear welted and are not as expensive as other brands can be. Another suggestion would be to visit the website for British firm Herring Shoes (www.herringshoes.co.uk) which offers deep discounts on English bench-made shoes (including Church’s, whose shoes can be seen in the pictures accompanying this article) and also offers factory seconds for sale (shoes that were deemed to have minor, often imperceptible defects and thus are sold at a lower price). In addition, Herring’s own brand of shoes are made by Loake, a respected English brand and therefore worth a look, particularly given the price which is less than $200CDN. In Canada, the old firm of Dack’s (www.dacks-shoes.com) makes good quality shoes that can be available on sale at decent prices. Finally, if one’s wallet does not allow an investment in welted shoes, Brown’s Shoes (www.brownsshoes.com) has their own brand of shoes that, while glued, often have higher quality leather uppers and can look far more expensive than they actually are (they just won’t last nearly as long as welted shoes).

If you’re feeling particularly flush, the best shoes in the world are made by makers including John Lobb, Edward Green, J.M. Weston, Berluti, Bontoni, Crockett & Jones and the Ferragamo “Tremezza” line

As a final note, it is best to not shop for shoes at the end of a busy day as one’s feet tend to swell from walking over the course of the afternoon. Leather stretches subtly and this will accommodate one’s expanding feet over the course of the day if the shoes fit correctly in the morning.

18 Responses to “Corporate Style: Part 2 – The Shoes”

  1. 1 Buck Coats
    November 23, 2009 at 3:15 pm

    wow. even better than Russell Smith.

  2. January 11, 2010 at 10:26 am

    what a great site and informative posts, I will add a backlink and bookmark your site. Keep up the good work!

    I’m Out! 🙂

  3. 3 Maerhyl
    June 19, 2010 at 10:28 am

    Take note that Dack’s shoes is out of business, sadly.

  4. 4 Andrew
    July 18, 2010 at 9:36 pm

    Love the blog! For a fashion neophyte like myself your lessons have been incredibly useful in helping me avoid dressing like a jackass.

    I’ve got what is probably a pretty stupid (and slightly embarrassing!) question to ask. But where’s a better place than this anonymous blog….

    Is there any particular way that dress shoes should be tied? I tie them much the same way I would sneakers, but I find that it bothers me how my clunky bow loops clash with my otherwise streamlined footwear. Do I just need shorter laces; or is there something that I’m missing?

    Thanks for the help and fantastic blog!

    • 5 canuckstyle
      October 15, 2010 at 4:39 pm

      Sorry for the very late reply to this question, but I’ve kind of let the blog slide (as you’ve probably noticed).

      You should tie your dress shoes differently than sneakers – with sneakers, most people use the typical criss-cross method. On dress shoes, you want the laces to go straight across (you can find how to do this online pretty easily). It’s a much cleaner, more formal look for dress shoes. As for chunky laces, I’d go and pick up some waxed dress shoe laces in the appropriate colours (remember to write down how many eyelet holes on your shoes as that’s how laces are typically measured.

      Good luck.

  5. 6 Aleeboy
    October 7, 2010 at 9:28 am


    Great write-up.

    I have a pair of JM Weston’s. It’s a pair of Conti Wingtip Loafers – believe yu have the lace-up pictured. It’s a lovely pair of shoes.

    However, the bottom sole is becoing undone from the upper. I understand that these are Goodyear welted quality shoes. Why is this happening to such a “Fine” pair of shoes?

    I am in Singapore. Can you kindly suggest whether this is fixable? If so, where I can have this problem fixed and typically how much?

    I would be most grateful to have your input.


    • 7 canuckstyle
      October 15, 2010 at 4:41 pm

      I’d have to take a look at the shoes to really see what’s going on, but I’m sorry to hear you’re having some trouble. JM Weston shoes are fantastic looking (I’ve never had a pair myself) and they’re a reputable brand. Your two options are to find a local cobbler (likely the cheapest and fastest option), or to send them back to JM Weston who likely have a program (like most other high end shoemakers) to refurbish them for a fee. Depending on how long you’ve owned them, and how big a stink you raise, they may even take care of that for free. If you’re unsure of who a good local cobbler is, you can either try contacting the store you purchased the shoes from or contacting JM Weston and asking for suggestions.

      Good luck.

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