Some days – for work, a function or just because you feel like it – you need to dress up. But there’s always that hesitation in having to don dress shoes – so often stiff, uncompromising and hard on your tootsies. At least, that was the case.

More relaxed dress codes, as well as the introduction of new technologies and ways of making shoes, mean you don’t have to be in pain for your style any more. Today, you can take a stand in shoes that won’t leave you bleeding and blistered, and you’ll still look the part.

Whether you opt for a shoe brand with an established reputation for comfort, are ready to play the longer game and break in a classic Goodyear welted pair, or opt for a more trainer-inspired, hybrid style, comfortable dress shoes are there to let you walk without wincing.

What Is A Dress Shoe Today?

A dress shoe used to be rather limited in style. For most men, well into the late 20th century, dress shoes meant dark (which really meant black), plain Oxfords – a slim-line lace-up largely free of decoration, with the exception perhaps of some light broguing. Buckles were out (too fancy). Loafers were out (too casual).

But with the shift in attitude towards office wear, smart shoes have also loosened up, at least in the styles available. It still largely rules out sports shoes or the likes of work boots, but the scope now includes monk shoes, Chelsea boots and chunkier looks of the kind that once would have been worn more for walking the dog.

Zara

“Men dress differently now, even when dressing up. You might wear shoes that contrast with your suit, for example,” says William Church, co-owner of Joseph Cheaney shoes, where sales of black dress shoes have fallen over recent years. “Colours the likes of chestnut and burgundy, or with burnishing – there are many more options. The possible details are almost endless and there’s room for quirkiness.”