The 5 Essential Pairs of Dress Shoes for Every Man's Wardrobe

Building a versatile and stylish shoe collection is a cornerstone of any well-dressed man’s wardrobe, especially in Singapore’s humid and hot year-round summer. Whether you’re stepping into the office, heading to a formal event, or enjoying a casual weekend, the right pair of shoes can make all the difference. Here are five essential pairs of shoes that every man in Singapore should own to ensure he’s prepared for any occasion.

Black Cap Toe Oxford in Black Calf Leather from Yanko, Retail Price: $478

1. The Black Cap-Toe Oxford

If you want to dress particularly smartly, a black shoe is indispensable, and a cap-toe oxford covers the most bases. An oxford is the smartest lacing style there is, and black is the smartest colour. The cap-toe design strikes a balance between a Wholecut Oxford—uninterrupted leather—and something more elaborate, like a Wingtip Brogue. A single leather sole is the most classic and preferred option for sleekness for such a pair of shoes. As a result, the cap toe oxford is suitable for black tie events when highly polished, understated, and perfect for any business suit. 

Oxford in Dark Brown Calf Leather from Yanko, Retail Price: $478

2. The Dark-Brown Oxford

Although a black shoe is essential in a smart office, many find they get the most use out of a dark-brown one. Dark brown works with most suits, such as blue or grey, and pairs well with a range of separate jackets and trousers. A dark-brown plain cap toe oxford or a half-brogue oxford, with its subtle detailing, makes it slightly more casual than a plain oxford, providing a small but notable distinction from the black shoe.

Penny Loafer in Dark Brown Suede from Yanko, Retail Price: $478

3. The Penny or Tassel Loafer in Brown

Arguably the most versatile shoe on this list, a pair of brown suede loafers are too casual for most formal suits but will pair beautifully with a casual linen or cotton suit. It works with almost any separate jacket and trouser combination, a pair of chinos and a shirt, and even some dark denim. It’s the shoe that’s suitable for everything except the most formal occasions. Suede might seem counterintuitive in a humid climate, but high-quality treated suede can resist moisture and stains, making it a practical choice.

You can opt for a Blake-stitched version such as our Yanko Belgian Loafers if you want an even lighter shoe, but a traditional welted shoe is preferred by many for the added durability. Belgian Loafers are designed with a low vamp, allowing for more give in the instep of the loafer, making it a more comfortable shoe for some.

Penny Loafer in Black Calf Leather from Yanko, Retail Price: $478

4. The Penny Loafer in Black Calf

We, Singaporeans, love loafers for their convenience, making it easy to slip shoes on and off, especially in a city where quick transitions between indoor and outdoor environments are common. Unlike more formal cities such as in the London or Tokyo, in Singapore, a pair of Penny Loafers in Black Calf are appropriate even with formal suits. If you wear a lot of suits for work, you should highly consider a pair of black loafers as your second pair of shoes.

Chukka Boot in Dark Brown Suede Leather from Yanko, Retail Price: $508

5. The Brown Suede Chukka Boot

This is not a smart office shoe but works well on a casual Friday or in a casual working environment, which is becoming more common in Singapore. Pair these boots excellently with grey trousers and a textured sports jacket. They are also ideal for weekends, looking especially good with jeans and an Oxford shirt. brown suede is the best colour choice for a first pair, with a second pair in tan or dark olive being a second versatile addition.

Once you have these the basic formal footwear to anchor your wardrobe, you can start being more adventurous with styles and colours, such as brogue shoes, light brown leather, and monk straps. With these essentials, you will have a solid foundation of quality shoes that will keep you well-dressed for any occasion, no matter the tropical and humid climate of Singapore.