Choosing the right shoe can be a challenge for many gentlemen. I’ve personally had many clients admit they only rotate between three types of shoes: ‘dress shoes’, trainers and thongs.

For me this is a shame. Diversifying your shoe choice is a fantastic way to mix up your wardrobe and instantly change the style, mood and formality of each outfit.

Below I’ve provided a few examples of what shoes you should consider for a few typical gentlemanly outfits. This should provide inspiration into what pairs you need to have as staples in your wardrobe.


You’re wearing: A pair of jeans or trousers and a t shirt.

What type of shoe should you wear? My first pick would be a clean, white leather pair of sneakers. This simple and classic look is versatile and will give you a stylish look in almost any setting. Wear your pair with no socks as this provides a much more polished look (If your feet sweat try wearing no show socks).

White Sneaker from AVAVI Paris

How they look on:

Dress down any outfit with a simple pair of sneakers


You’re wearing: A pair of tailored trousers, open dress shirt and a jacket.

What type of shoe should you wear? The above staple look commands a shoe that is sophisticated and fun. You’ve lost the tie (and potentially jacket), so you need something edgy yet still formal. A leather or suede leather tassel loafer is the perfect fit and will superbly finish your look. If I lose the tie I generally lose the socks too to match the level of formality.

Italian Leather Tassel Loafer from The Bespoke Corner

How they look on:

But if you’re not in the city and perhaps heading to a lunch on the weekend – try a driving loafer…


You’re wearing: Staple navy suit, white shirt and knit tie.

What type of shoe should you wear? Most gentlemen here will say ‘just a dress shoe’ which is a shame given there are so many types each with their own benefits and level of formality. Walking into a quality shoe store you could come across Oxfords, Brogues, Double Monks, Single Monks, Loafers, and Boots each with their own internal anatomy (for example, the Wingtip Brogue vs Semi-Brogue).

To keep things simple the staple dress shoes I recommend to my clients are Oxfords, Double Monks and Loafers. Each shoe is appropriate for business wear yet provides a different level of formality and style allowing you to diversify your look for every occasion.

If you’d like to check out more shoe options Mr.Porter has a great guide here.

Image result for john lobb double monk

Brown leather Double Monk from John Lobb

How they look on:

Black Tie

You’re wearing: A limited edition Bespoke Corner Rolls Royce Tuxedo.

What type of shoe should you wear? You’ve certainly got the right suit on so it’s essential you also nail the shoes. Many gentlemen daunt the thought of dressing for black tie which I’ve never really understood. The fairly strict dress code should make it simple as your options are limited. In terms of shoes, there’s only really three types I would recommend: lace-up oxfords, Belgian-style loafers and slippers (commonly referred to as Prince Albert slippers. Opt for a patent leather or velvet as it pays homage to the formality and grandness of the night.

Velvet Slipper from Churchs

How they look on:

Choosing the right pair of shoes can be difficult when you’re faced with so many different options. If you have any questions or would like to speak further, please get in contact.

Miles Wharton – Founder – The Bespoke Corner

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