Shoes make the man – the quality of your shoes reveals how much you respect yourself. While not necessarily a good thing, people may make judgements about your occupation and income just from what you wear, and maybe even what you’re like as a person – shoes are like a resume on your feet.
Just like with every other accessory in a man’s wardrobe, there is a struggle to find something you like and one that abides by unwritten time-honored codes. In fact, insecurities over which design to wear has spawned an entire dedicated HardwareZone thread that has been active for 7 years!
If you are a job-hunting graduate or just someone getting your first pair of work shoes, the ideal pair should lend you a professional edge to land a job, while being affordable enough to pay for itself quickly.
3. Plain Captoe Oxfords
Of the 3 styles in this list, the cap-toe oxford (aka blucher) is the most formal, also making it the least versatile. However, it is a top choice if you are applying to formal offices like legal and financial firms.
Oxfords are characterized by a closed lacing system, which is when the vamp of the shoe is sewn to the quarters so that the entire shoe upper feels like one continuous piece.
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Because it is meant to be a formal shoe, your cap-toe oxfords should be plain (no brogueing) and black. Otherwise, you’ll be stuck with a shoe too casual for a formal setting, and too formal for most occasions in Singapore.
Allen Edmonds Park Avenue Cap-toe Oxfords in black; retailing at $395
2. Monkstraps
Laced shoes are generally more formal than unlaced ones. With the laces replaced by a leather strap and buckle, monkstraps come in as the least formal of our shortlist. This makes the monkstraps an extremely versatile design that can be worn with pants, jeans, and even the right shorts. Having to own just one pair of shoes for work and play makes monkstraps an extremely cost-effective option. However, do note that while monkstraps may be suitable for daily office wear, they may be considered too casual for business formal and definitely do not belong at black tie events.
Just like loafers, monkstraps are supposed to be slipped on and off – you are not supposed to unbuckle them. However, their cut makes them more formal than loafers and suitable to be paired with suit pants.
Get monkstraps in a variation of brown for maximum versatility.
Cole Haan Cambridge Monk Straps in British tan; retailing at $258.
1. Dark Brown Derbies
Also known as balmorals, derbies look very similar to oxfords. The key difference is that derbies use a open-laced system: the vamp is not sewn into the quarters, which makes the vamp look like 2 separate leather flaps over the main shoe body. Because of this, the formality of derbies lie somewhere between oxfords and monkstraps, though tending more towards its close-laced counterpart.
As the primary purpose of the shoes we cover in this article is work, the derby is our top pick because it is suitable for a larger range of work occasions than the monkstrap, while still being versatile enough for smart casual wear (unlike oxfords). The classically stylish derby will give your ensemble an edge over your colleagues totting square-toe loafers from the departmental store. If you wear derbies in a shade of dark brown, you can easily swap out your work pants for a pair of jeans after work and head straight to the pub.
Ed Et Al Waterloo derbies in dark brown; Retailing at $349
Broguing
Brogue shoes are leather shoes in any style that have decorative perforations punched along the stitches. Broguing on shoes are segmented into 4 classes by the extent of broguing: Quarter Brogues, Semi-Brogues, Full Brogues (Wingtips), and Longwing Brogues, in order of increasing decorativeness.
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Broguing on shoes is something you’ll want to consider if you like formal cuts but are afraid that it doesn’t fit into your casual office environment. In general, the more ornamentation a shoe has, the less formal it is e.g double monkstraps are less formal than single monkstraps. This means that brogued oxfords are less formal than a plain oxford, and longwing brogues are less formal than semi-brogues.
INVESTING IN QUALITY LEATHER
When buying work shoes, always get a pair made of full-grain or at least top-grain leather, the 2 most durable layers of the cowhide. They may cost a few dozen more at about $300 – $500 a pair compared to their ‘genuine’ leather counterparts, but will also last years longer.
There is a false belief that leather is delicate and very hard to maintain. With quality leather, care can be as simple as applying a small amount of conditioner once a month. Leather conditioners are lotions or creams that restore the oils inherent in leather, keeping the fibres strong and supple.
Saphir Renovateur Leather Cleaner and Conditioner; Free Shipping within select countries by The ShoeTree Project
Never be tempted to get a cheap pair of mass-produced synthetic shoes. Not only do synthetic shoes make you look undiscerning, there is also nothing affordable about them at all. While leather, an organic material that was once alive, responds well to proper care, there is nothing you can stop the quick degradation of synthetic shoes. Synthetic shoes will break down within 1 to 2 years, and look old and frumpy long before that. On the other hand, quality leather shoes can last at least a decade with proper care, which means they cost you an average of $30 – $50 a year at the maximum.
