The shoes every stylish man should own

We invited Craig Langdale, editor of men’s fashion and lifestyle site MenswearStyle, to choose the key shoe styles that should have pride of place in the discerning gentleman’s wardrobe. The selection and styling advice that follows is by no means exhaustive, but it explains why there’s more to men’s shoes than having a signature pair.

Oxford Shoe
Named after Oxford University, even though the shoe was originally found in Scotland, the Oxford shoe style is great for everything. With this style available in so many different materials and colours, you won’t be hard done by to find something that suits you. Using leather for suits and suede for smart-casual means you’re good to go before you’ve even decided what outfit to wear. Just make sure to look after them.
Chelsea Boot
The Chelsea Boot was originally a women’s shoe style. More recently this has been trickling into men’s fashion and rightly so. The boot has an elasticated side to help pull them on which allows easier access but also keeps the shoe tight around your foot. As the boot has this elasticated cut out, working these into an outfit with skinny jeans will sharpen up your bottom half by keeping it tight and defined.
Brogue Shoe
The rustic design which features on the Brogue shoe gives an intricacy to your style that provides the impression that you spend time thinking about what you wear. The style is a lace up type with a solid shape that a shoe-tree would be great for maintaining. A slim pair of jeans rolled up to allow the shoe to be fully shown is a great way to display them, and a tan or brown option would look great with denim of any colour.
Monk Strap Shoe
Double strap, single strap or a low topped buckled boot are some of the options of a Monk shoe. With a technical design that uses no laces, only buckles, they look great under a pair of suit trousers. In terms of formality though, the Monk shoe style is less formal than an Oxford but more so than the tan Brogue. The slight heel that some of the shoes have will give you a little extra subtle height, but also the range of colours available gives you the versatility to round off your style for any occasion.
Desert Boot
Desert Boots are almost posh high-tops, worn by the British Forces in World War II. The Desert Boot (such as our Sahara style), used to be made with calfskin leather, but more recently the use of worn suede has given the shoe a smart sandy look. Finding the right boot for the mood is a little harder here as they’re predominantly a smart-casual uniform wear shoe. Using darker colours with some fitted suit trousers, making sure to not clash the colours too much, is a great way to style them.
Penny Loafer
Pull-on shoes could bring back memories of horrible, wrinkled faux leather shoes you were forced to wear back in Primary school. But a well-made, smart Penny Loafer is a good option for easy, comfortable wear. The shoe has no buckles or laces, a solid shape and is one of the most versatile formal shoes you can own. The Penny Loafer isn’t a smart-casual shoe by any means, but if you’re feeling a little brave then wearing slim light trousers or formal chinos and no socks will bring the shoes into the outfit.

2 Comments on “The shoes every stylish man should own

  1. Nice piece, although I’m sure you’re expecting, perhaps even seeking some debate! I’m 100% with you on the Oxfords, Monks, brogues and Chelsea boots (although mine are my only pair of smart, non-Loakes … Italian Beatle Boots with Cuban heels!). I’m living happily without desert boots and loafers, but my boat shoes are pretty essential to summer life. My Shilton boots (black and brown pairs) are definitely winter essentials and I’d add a pair of Spectators for those “look at me” moments.

  2. I love Loake and I own a pair of brogues given by my wife a couple of years ago. The leather is superb and made with high-quality – love it.

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