Stylish from the ground up

As the saying goes, 'if the shoe fits, wear it'. That's all well and good, but what if you have no idea about what kind of shoe you should be wearing in the first place?

Now, my working knowledge of traditional men's shoes isn't that flash; I confess I have so far survived on simply being able to tell the difference between brown and black leather.

But apparently, in order to be a man today, being sartorially savvy is as important as knowing your way around a carburettor. Of the two, shoes seemed to be the most accessible, so I decided to start my journey into true manhood there.

“For some men [buying shoes] is a chore,” says Lisa Joseph, co-owner of Joseph's Shoes in Sydney's Strand Arcade. “There are men who stick to a certain style and repeat year after year … but more than ever there are now men who love to follow trends and love the experience of shopping and new styles. Thankfully this is a growing market as men are becoming more interested in different looks.”

There are plenty of options out there for adventurous types. But for men who, like myself, can only move in baby steps when it comes to trying new things, there are really only two styles that you need to know – the Oxford, and the Derby. Whilst the odd pair of desert boots or chukkas might find their way into your wardrobe according to seasonal trends, when it comes to traditional shoes these are the building blocks of male footwear.

“Oxfords and Derbys are the main categories of men's lace-up dress shoes,” Lisa explains. “And they're distinguished by their lacing systems. Simply put, the Oxford has a closed lacing system that is a more streamlined look. The Derby is an open lacing system, is easier fitting and lends itself to a more casual look. And the term broguing simply relates to the symmetrical punching and perforations on the shoe.”

So with that in mind, which shoe fits which occasion?

“The Derby is perfect,” says Jess Cameron-Wootten, director of bespoke shoe label, Wootten. “I would always recommend a Derby if you are planning to have an everyday shoe. Plus if you have a high instep or you find your feet swell during the day, they are ideal as they can be more easily adjusted to remain comfortable. The Oxford, however, is the classic dress shoe, and is traditionally worn as a business shoe.”

When it comes to fitting your shoe, it all comes down to how broad the section across your toes is. For the average shoe – or a rounded toe – Jess recommends a rough three-quarters-of-an-inch room between your toe and the tip of the shoe. “The more tapered the toe, the longer the shoe will be. The broader the toe, the shorter you can afford to go. I would always recommend to buy shoes that are snug without being uncomfortable. And if they are made of a quality leather and cut in the correct fashion they will always give a little and mould to your foot with wear.”


When choosing your shoe, the type of leather used in its construction is as tantamount to the shoe's lifespan as the fit. “I would always advise against patent or foiled – artificially finished leathers – for comfort and longevity,” says Jess. “The surface of a patent is generally a plastic coating and often patent is made on a split – not a full grain – leather. This means that it will not breath as well, will often be stiffer and less malleable, and the surface can crack and delaminate after some wear. For a dress shoe I would recommend a fine grain full-grain leather, whether it be bovine, calf, kangaroo, or whatever.”

But if you are after the ultimate investment in footwear, nothing beats your own bespoke shoe. Melbourne-based Wootten is one of only a handful of traditional leather workers operating in Australia which still hand-makes custom footwear. Just like a tailor-made suit, bespoke shoes are fitted perfectly to the shape, width and length of your foot.

Whilst choosing bespoke might end up costing you a little more, the benefits far outweigh the dent to your credit card. At Wootten, the average cost of a pair of hand-made shoes tailored to your feet will set you back a rough $750.

And whilst some of our female counterparts are convinced that every occasion requires a different kind of shoe – preferably new – the average male can probably get away with having just one go-to pair of fancy kicks. But the style you choose will be entirely up to you, with both options having their benefits.

“The Oxford is the most traditional,” Lisa suggests. “Everyone should own at lease one pair of Oxford toecaps, as they are the most formal and the perfect companion to the classic business suit.”

“I would start with a Derby construction,” Jess counters. “I have a fairly simple aesthetic, so my ideal shoe would have a classic silhouette, be a two- or three-hole Derby and made in a London/Saddle tan with a waxed leather sole. Lighter colours can be dressed up or down, with a navy or grey suit or a pair of chinos or denim. A good all-occasion shoe.”

What style and brand of shoe is your favourite?