Investing in a shoe collection: Part I

So I hear a lot of guys say “I’m looking to spend some money on a decent pair of shoes, but I don’t know where to start”. And usually people start throwing brands or advice at them about what’s good but really a lot of that is just their own preferences. To build up a shoe collection, you must first understand the language of shoe styles, what they convey, and what you intend to use them for.



I often hear or read the advice “buy a pair of expensive, well-made black oxfords – it will be the most versatile. You can wear it to weddings and funerals and interviews …”. I don’t own an expensive well-made black pair of oxfords because I don’t go to weddings, funerals and interviews everyday. My workplace (as most in Australia would be, even in a corporate setting) is pretty casual. Business casual is not what it used to be, and I even see some guys walk about in timberlands. So the shoes I have invested in tend to be brown and more casually styled, like derbies and boots. What makes a shoe more casual or formal?


Formality is usually inversely proportional to darkness. Black is the most formal, followed by dark brown, then as the shades go down to light tan, it becomes the least formal. This is why you wouldn’t wear a brown pair of shoes to a funeral, and I generally don’t wear black shoes to work most days of the week.


Smooth leather is the more formal. Shiny (patent) leather is the most formal and is often used for shoes to be worn with tuxedos. Textured leather like pebble grain/scotch grain are more casual as are suedes. Roughout which is basically unsanded suede is less formal still and usually used for boots.


Oxfords (also sometimes called balmorals) are generally more formal because the shoelace tabs finish up under the vamp. You get a cleaner look – see this Allen Edmonds Park Avenue for example. The opposite of this is the derby (also called bluchers) where the eyelet tabs are stitched above the vamp – see this Alden NST. The look is less sleek and therefore less formal.

When it comes to adornments, the less adornments or less busy the shoe is,  the more formal. At the most formal end of the spectrum you have a wholecut shoe where the upper is made from a single piece of leather. This is closely followed by the captoe-oxford. The less formal shoes generally have perforations known as broguing. The perforations are usually on an extra bit of leather that covers part of the vamp and the sides of the shoe. If the extra leather stops below where the eyelet tabs end, they are called shortwings, and if it continues all the way around to the heel, they are called longwings (more common on American-style shoes). The broguing can also be done on a captoe. There’s no hard and fast rule here but generally the more broguing and the busier the shoe looks, the less formal it is.

So you’re gonna spot a trend here. The heavier the sole the less formal. So a very formal shoe will generally have a single leather sole. More casual dress shoes might have a double leather sole, or a clunkier looking storm welt. More casual still, you might have some rubber lugs under the leather, or the sole might be made of rubber entirely and have big lugs for traction, like on most boots.


This one is pretty obvious. If the shoe is sleeker, it will look more formal. If the toebox is very bulbous or rounded, then it will look more casual. Likewise certain styles like moccasins (think boat shoes, camp mocs, blucher mocs) tend to be quite casual.

Think before you invest

So think about what you are going to use your shoes for and think about what types of clothes you are going to wear it with. Large shoe makers like Allen Edmonds or large shoe sellers like Pediwear have a huge range of styles for you to browse and see what you think look nice, even if you are not eventually going to buy from them. Once you have narrowed it down a bit, look on pinterest to look at what other people wear with your chosen style. Go to some physical stores to try on some similar styles. And above all, be patient. You might keep a decent pair of shoes for 20 years. Don’t rush into this long-term relationship.

Like I said, my workplace is business casual and fairly relaxed. I have a lot of shoes but the 3 most frequently worn shoes in my collection are: a pair of mid-brown pebble grain brogued longwings, a pair of snuff suede chukkas, and a pair of brown American work/military boots.


Coming up in part II: season appropriateness, $$$, and where to buy.

4 thoughts on “Investing in a shoe collection: Part I

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