The winter shoe guide: footwear for every occasion

Footwear is the most important aspect of your attire, or so they say. Supposedly women (and men) take note of what’s on your toes before they sample everything above the ankle. The adage has also probably become closer to the truth than when it was first coined; our eyes being constantly glued to a screen means our peripheral is often littered with nothing but feet.

Men’s footwear, unlike women’s, should be an easy decision however – despite the added importance. It’s really should be a case of slip on and go, rather than deliberating back and forth over whether the wingtips, derbies or oxfords are more appropriate. Bring your shoe rack up to speed with our definitive primer to this winter’s shoes:

Really you could get away with just two pairs here, a black pair and a brown pair. There are of course nuances to that but one black, one brown which are neither too square, nor too pointed is the basic framework for on point formal footwear.

Office

London Leather Oxford Brogues, £295.00 from Church’s

Ideal in every single work situation, a conservative oxford brogue can do no wrong. The punching on these Church’s isn’t too, well, punchy, and the shape is simply perfect. They’ll pair with every suit you could ever wear to work, grey, navy and if you’re into that kind of thing, black.

Wedding / Smart Event

Lowndes Double Monk Shoes, £405.00 from Crockett & Jones

Give the office shoes a day off when it comes to going out to dinner or a wedding – yes, some people do decide to tie the knot in the winter. In this instance a good dark brown pair comes into play.

A monk strap is a bit more interesting but a pair of derbies in the same shade would be just as suitable. Again, they’ll go well with any suit except for black, and the only time you should be wearing a black suit to these kind of things is if it happens to be a funeral – and you’ve got those Church’s for that.

Black Tie

Poltier Patent-Leather Derby Shoes, £400 from Mr. Hare

And if you’re frequenting black tie functions on a regular basis, i.e. more than once a year, consider some patent lace ups to really top off that tux.

The most frustrating of invitations is easily decoded through a pair of tan brogues. You wouldn’t go this bold to the boardroom, and they look as good with a pair of jeans as they do some tailored trousers: perfect smart casual wear.

Drummond Derby Shoes, £390.00 from Crockett & Jones

Put a bit more thought into your weekend ensemble with a pair of shoes that aren’t scuffed to death or just “comfortable”.

Everyday Off Duty

Stan Smith Leather Sneakers, £70.00 from Adidas Originals

A bit more freedom comes into play here depending on personal style, but in reality you can strip it back to just two styles which would cover every single base.

Firstly, a simple, pared-back sneaker (or trainer). These are having a bit of an extended moment in menswear and now, heaven forbid, even becoming acceptable to wear with a suit. Opt for something neutral, minimal and low key, an Adidas Stan Smith or Common Projects’ Achilles is the model to follow.

Tenor Chelsea Boots, £195.00 from Reiss

Next up, the Chelsea boot. The shoe of the year by a country mile; lump for leather rather than suede in the winter months, principally for practicality if nothing else. If you categorically not a trainer man, these look as at home alongside a suit, as they will a pair of jeans.

Wet Weather

Rubber-Soled Leather Boots, £240.00 from Red Wing

Winter may be the season of the gentleman, but the rain is a serious sartorial dampener. Whilst a good umbrella and even a pair of discreet galoshes can help you survive it during the week, on the weekend break out something a little more specialist. American heritage brand Red Wing do a timeless boot that is perfectly equipped for dealing with the season’s most unforgiving elements.

Country Weekend

Cheyanne Leather And Rubber Boots, £110.00 from Sorel

And when the city gets too much and you have to retreat to the country, take proper preparation and pack a pair of duck boots. There’s a bit more about them then a pair of wellingtons and Canadian label Sorel are experts in the craft – you’ll struggle to find a situation they can’t handle.

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