It's probably the worst style sin a man can make: wearing cheap shoes.
Made from poor-quality leather, that is cemented to a second-rate rubber sole, the result is enough to make your toes curl. Quite literally as poorly made shoes will all too commonly lift at the toe.
While it can be easy to resolve to never buy another pair of toe-curlers again, the next part of the shoe buying journey becomes a little more difficult. Where to start? What should you really be looking for and how much should you pay?
A quality leather
You might think leather is leather, but when it comes to shoes this is certainly not the case. Especially, if you want a pair that not only lasts but gets better with age.
"In my opinion you can't go past calf leather," says Ray Willmoth, a former shoe buyer with Charles Tyrwhitt and the Australian distributor of UK shoe manufacturer NPS.
"As anyone with a pair of calf leather shoes will tell you, the leather moulds to the unique shape of your feet and becomes more and more comfortable with each wear. Condition them regularly with a quality cream (preferably mink-oil based) and a beeswax polish and the leather will become soft, supple and develop a beautiful lustre. Before long you'll think you're walking along in a pair of silk slippers."
But the benefit of calf leather isn't just to do with look and comfort. Willmoth says properly nourished a calf leather shoe can last decades and will even improve with age.
"I've seen calf leather shoes 30-years old that look absolutely fantastic."
Undoubtedly, the way a shoe is built, or how the upper is attached to the sole, tells you a lot about its quality.
As Willmoth notes, a Goodyear welted shoe (which can be resoled many times over the life of the shoe) is one of the traditional hallmarks of quality.
"Over 200 steps are typically required to make each pair of shoes. And generally, because it's such a labour intensive process, manufacturers won't make a Goodyear welted pair of shoes with a rubbish leather," says Willmoth.
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But that's certainly not to say that other construction techniques use inferior leather. Some manufactures, especially in Italy, use quality calf leather to make shoes with the blake stitch method, in which the upper, insole and sole are combined using a single stitch.
"The advantage of a blake stitch construction is that the shoes typically have a slimmer silhouette and are initially more flexible than their Goodyear welted cousins."
Yes, they cannot be resoled (at least anywhere near as easily) but then again, maybe you don't see yourself wearing the same pair of shoes in 10-20 years' time. If that's you, don't be afraid to buy yourself a quality pair of blake stitched shoes.
Are you really buying handmade?
'Handmade', is one term you'll frequently see used by many ready-to-wear shoe brands. However, Willmoth says it has become so overused as to be rendered nearly completely meaningless.
"The term 'handmade' should only apply to bespoke shoes where every stitch is made by hand, which for a Goodyear welted shoe typically costs up to $6000. In all other instances the word simply refers to the fact that a hand was on the shoe as it was being guided through a machine."
So the term 'handmade' is stretching the truth but should you care? Well, not really, not unless you're forking out six grand.
"The quality of Goodyear welted shoes, especially those made in the UK, is of a very high-standard. It's not like they throw it in the machine and it pops out," says Willmoth. "At every single point, at every stitch there is a pair of hands on the shoes carefully working the product. There's certainly a high level of craftsmanship in their production."
The bottom dollar
The cost of quality leather and an exhaustive production process should tell you that high-quality leather shoes, especially the Goodyear welted variety, usually don't come cheap.
Why that may come as no great surprise, you may be left scratching your head wondering what the difference is between a pair that you can buy online for $300 and a pair that retails for over $2000.
As Willmoth explains, the reality is you're getting a great product at both price points, but how much you want to spend really boils down to what you want and what you value.
"Some brands produce a very small number of shoes to extremely high standards with large amounts of time spent on hide selection and finishing (burnishing and polishing the leather), which ultimately means a much more expensive product," says Willmoth. "Obviously pricing for exclusivity also comes into it, as does supply and demand."
"The reality is, if you take good care of them, buying quality calf leather shoes is always money well spent."
How much are you willing to spend on your shoes? Tell us in the comments section below.