Hello everyone, and welcome to another Singaporean article! On this shiok Sunday, I’m doing an informative article on the 5 types of dress shoes that, in my opinion, every gentleman should own.

Dress shoes come in many forms – do you know the difference? Pictured shoe is the Gaius Walks Romeo Cap-Toe.

Dress shoes come in numerous forms – some are more suited for certain occasions than others. If you don’t know much about dress shoes, don’t fret as this is what this article is for! There are 5 types of dress shoes that I feel every guy should own, and I’m going to explain why below. Let’s get into it!

1) Cap Toe Oxfords

The wardrobe staple – if you can only have one pair of dress shoes, it has to be the cap toe oxfords.

A timeless classic.

Let’s start with what an oxford is. Oxfords generally refers to dress shoes with a closed lacing system, and is by far the common type of dress shoe worn. Cap toe oxfords refers to oxfords that features a ‘cap’ at the front, giving the shoe a three-part look. As a starting point, I would recommend a pair of black cap toe oxfords (as pictured above). You can wear a pair of black cap toe oxfords with literally anything – a black suit, a navy suit, a white office shirt, and even with a tuxedo! You will definitely get a lot of mileage out of a pair of black cap toe oxfords, like this one I have from CustomMade. If you already have one, you can then opt for a nice brown pair, like the Gaius Walks Romeo Cap Toe in the featured photo of this article.

When to wear cap toe oxfords: Everyday to the office.

Affordable recommendations (under S$200): Gaius Walks Romeo Cap Toe, Arden Teal Calafate Blake Stitched Oxford, W.H.Y & Co Hugo

2) Wholecuts

For those that already have a pair of cap toe oxfords, the next pair to get would be the wholecut.

Ain’t that beautiful?

A wholecut is considered a type of oxfords due to it having a closed lace system. However, unlike most oxfords – such as the aforementioned cap toe oxford – a wholecut is, as the name suggests, made entirely from a single piece of leather. It’s more minimalist and elegant than the cap toe oxfords, and is best worn when you want to turn the formality up a notch. Personally, a wholecut is my dress shoe of choice when I’m attending events, weddings, etc. I love the way a wholecut showcases the beauty of the leather it uses – it makes the leather the star of the show. Just look at my Gaius Walks Andres Wholecut above!

When to wear wholecuts: To events, weddings, functions etc where you want to appear a little more formal.

Affordable recommendations (under S$200): Gaius Walks Andres Wholecut, Arden Teal Carlota Blake Stitched, W.H.Y & Co Hans

3) Brogues

Unlike the wholecut, brogues lies on the more casual end of the spectrum.

Brogues make for a more striking look.

I always love a pair of brogues, such as the W.H.Y & Co Qi shown above. It’s the perfect choice if you want to dress down and stand out, but still remain formal enough for the office or a meeting. For those uninitiated, brogues refers to a pair of dress shoes (usually oxfords, though not always) that has a decorative element of perforated holes, otherwise known as broguing. While generally considered inappropriate for more formal attire (black-tie tuxedo, three-piece suits, double-breasted suits, etc), a pair of brogues is nevertheless versatile enough to be worn with anything from a suit and tie, to even a pair of jeans! All men should have at least one pair of brogues in their closet.

When to wear brogues: When you’re trying to appear a tad less formal, less stuffy, but still appropriate. Great for either dressing down office wear (suit and tie), or dressing up casual wear (buttoned shirt and jeans).

Affordable recommendations (under S$200): W.H.Y & Co Qi, Gaius Walks Franco, Arden Teal Tartagal

4) Monk Straps

If you’re not a fan of brogues, why not try a pair of monk straps instead?

Or you could get a Monk Strap with broguing – the best of both worlds.

Not everyone is into brogues – some say it triggers their trypophobia. If you’re one of those, why not try a pair of monk straps? Monk straps refer to dress shoes that don’t have laces. Instead, the shoe is fastened by either one (called a single monk strap) or two (a double monk strap) buckles and straps. I would say that monk straps are about as formal as brogues, and is a good option for those who wish to be different. Chances are, most people in the office are wearing oxfords – if you don’t want to fit in, wearing a pair of monk straps is a good way to stand out. Personally, one of my favourite style combinations is pairing a double-breasted suit (which is a very formal look) with a double monk strap to dress it down. Credit where credit’s due – I got the rakish inspiration from He Spoke Style. It’s a great way to dress down an outfit, while remaining entirely appropriate for work and other formal occasions.

When to wear monk straps: When you want to inject a bit of flair into your outfit, while remaining appropriate in formal situations.

Affordable recommendations (under S$200): Arden Teal Cordoba Double Monk, Gaius Walks Gianni Single Monk, W.H.Y & Co Kenny

5) Loafers

For a more casual spin, try on a pair of loafers!

An essential for smart casual.

Loafers are the perfect dress shoes of choice for a smart casual look. Loafers come in many forms – there are suede loafers, leather loafers, tassel loafers, penny loafers, etc. The one I’m wearing above (the Scofield Penny) is a leather penny loafer, which is a more formal loafer. Loafers are perfect for significantly dressing down a suit, or dressing up a shirt/chinos combination on a date night out. Loafers aren’t appropriate for formal, or arguably even work occasions, but personally they are one of my favourite types of dress shoes due to their comfort on the feet. I also love pairing a suit/T-shirt combination with a nice pair of loafers – always perfect for an evening out.

When to wear loafers: When you want to dress down a suit, or dress up a shirt/chinos combination. Perfect for smart casual occasions, such as a date at a restaurant, a trip to the theatre, etc.

Affordable recommendations (under S$200): Scodield Penny, CustomMade Suede Loafers, Gaius Walks Paolo Napa Leather Loafers


I hope that this article has been informational to you! In my opinion, all men should have at least one of each of the aforementioned 5 types of dress shoes in their closet. Each type of dress shoe has a specific purpose, a scenario to be worn in. Having at least one of all 5 should cover your bases for any conceivable sartorial situation that you might find your dapper self in!

For those who already have all 5 of the aforementioned types, you can try adding a wingtip to your collection! Pictured is the Scofield Cavalier.

If you’re wondering where to get affordable dress shoes from, don’t fret! I’ve partnered with multiple local shoe brands – Arden Teal, Gaius Walks, Scofield, W.H.Y & Co, CustomMade – that make great shoes at affordable (sub-S$200) price points. I’ve also previously reviewed shoes from each of them, so be sure to check out the individual reviews of the brands! For those interested, you can use the promo code “WAHSOSHIOK” to get a myriad of discounts from the aforementioned brands. Now that the circuit breaker is finally over, why not get yourself a pair of nice dress shoes to return to work?

View Arden Teal’s full range of offerings here.
View Gaius Walks’ full range of offerings here.
View Scofield’s full range of offerings here.
View W.H.Y & Co’s full range of offerings here.
View CustomMade’s full range of offerings here.

P.S Do check out the new “Discounts!” page for exclusive discounts for Wahsoshiok readers! More brands will be added very soon – stay tuned!

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P.S.S.S Shiok is a common word Singaporeans use to express admiration or approval. As of 2016, you can find the definition of the word in the Oxford English Dictionary.