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What are the right business shoes?

What are the right business shoes?

To quote Hardy Amies :

“A man should look as if he had bought his clothes with intelligence, put them on with care, and then forgotten all about them.”

“It is totally impossible to be well-dressed in cheap shoes".

In this guide, we take a look at the most prominent men's business shoes and lead you through the associated expectations of each style. What should you wear to work an event and casual Friday drinks? Should you keep it relaxed or formal? We will investigate fine leathers and soles for dancing, an introductory guide to choosing the best men's business shoes.

The Wing-Tip

Starting with a slightly casual affair, the brogued wing tip is the more relaxed brother of the Oxford family. The Oxford brogue featured here sports a full wing tip and brogue detail, constructed from malleable calfskin. We suggest wearing these for work or casual, through the weekend at a family lunch or Sunday drinks with friends. These are a great choice for those looking to maintain style when the occasion is a little more low key. this style looks good with a suit or chinos.


brogue wing tip shoe



The Derby

The open laced incarnation of the Oxford shoe, the Derby, is a great mid-point for those seeking a shoe that at once both conveys a sense of sophistication and ease. Featured here, The Charlton is constructed from black box calfskin with a tan leather lining and natural shine to finish. This is a great fitting shoe for the working week – a style we’d don for the office and lunch with colleagues. While it doesn’t quite meet the formal standards of the traditional Oxford its timeless simplicity offers an effortlessness that’s hard to find elsewhere. Due to their versatility, we often pair this style with well-fitting suit pants or fine woolen trousers.

derby shoe


The Oxford

Arriving at the Oxford, this closed lace construction epitomizes the classic dress shoe. A pair of simple Oxford’s will never go astray and while they tend to befit more formal occasions, their modest design means that they’re quite comfortable in an easy-going environment. For special events, we’d suggest the Oxford silhouette in a high gloss leather but for weekday meetings or presentations, a Brown or chocolate calfskin (such as the Beauford featured here) would be most adaptable. A quality brown leather tends to complement most textiles and palettes so it’s a great staple to have on hand. The best Oxford shoes will exude a sense of minimalist durability, truly an extension of the man who wears them.


The Monk Strap 

Falling somewhere between the Derby and the Oxford in terms of formality, the Monk Strap has made its way through a number of different trends over the years. While the buckled silhouette is not as simple as its laced counterparts, the humble Monk has made its way into the hall of timeless designs. Sporting a single or double leather strap, the Monk Strap is a really smart and comfortable way to stand out from the sea of oxfords and derby shoes. Its unique silhouette exudes personality and is an excellent addition to any ensemble that needs that extra je ne sais quoi. We love seeing this style paired with cuffed denim for a dose of weekend nostalgia or a deep navy suit for the working week. We also really enjoy seeing men play on the buckled focal point with vintage jackets that sport matching hardware and buckles. The best men's business shoes toe the line between a conservative style and added panache. We think the Monk Strap (such as this one in black box calf ) is the perfect solution for dapper men who want to look good and stand out.

monk strap shoe

The Opera Pump 

For those seeking men's dress shoes online, the traditional Opera Pump stands out in more ways than one. Conventionally constructed from a black patent or high shine leather, the Opera pump was initially worn with silk stockings and breaches by European Gentlemen for evening affairs. Today, the classic pump is most commonly worn when paired with a sophisticated white tie tuxedo. Often selected for their slimline and subtle touch of class, the shoe can be defined by small silk or grosgrain bow designed to complement the necktie and create the illusion of a smaller foot. As the shoe of choice for those planning on hitting the dance floor, the pump must be fitted seamlessly to prevent any slipping at the heel. Traditionally made from a high gloss patent, the leather is designed to reflect the silk facings woven through the matching tuxedo. Hand made dress shoes like the A. McDonald Opera Pump is hard to come across these days, but when one finds the right pair, there’s nothing quite like it.

opera pump shoe


Choosing the right dress shoes does not need to be a complex business. Rarely are the conventions of footwear explained to us and instead, we’re left to muddle through the ins and outs of Derby lacing and Oxford brogueing on our own terms. We hope this short guide to men's dress shoes is of use and that next time you’re buying oxford shoes online or hunting down the perfect companion to a new tuxedo, you find your way back here for a little guidance. You’re also always welcome to browse through the A. McDonald online store for inspiration and directions. Handcrafted in Sydney, Australia the boutique workshop also takes custom orders for those looking for something uniquely their own.

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Free shipping and returns on all full price items over $200 to Australia.