The 5 worst men’s shoe styles of all time

Footwear is often hailed as the foundation of any good outfit. Excellent style is rooted, it’s said, in a man’s choice of watch and shoes. In reverse, an atrocious choice of footwear is irredeemable, sinking your attire and any prospects with it, quicker than a lead balloon. These are the most heinous of options you could possibly slip on and ones that no gentleman should ever be caught dead (or alive) in.

The shoe is seemingly universally unloved yet somehow still manages to make an appearance on every commuter train in existence. There’s no excuse for these monstrosities at any time or place – they are downright disgusting and only serve to drag you down in everyone’s, and I mean everyone’s, estimations. A shoe should, to some degree, follow the shape of your foot and last time I checked, my feet (or anyone’s I know) aren’t angled off at a perfect 90 degrees at the end.

Wear these instead:

Aldo Welidama Leather Shoes

These just don’t look good and unless you’re at a pool or in a gym shower, there’s no reason for these to be any where near your feet. Firstly, they’re hardly the safest of shoes – don’t come crying to us when an escalator eats half of your toe, or a phalange gets broken during the scrum to get on and off the Tube. Then there’s the fact that not only is the shoe, if we can call it that, ugly as sin, everyone’s got to look and smell your hobbit feet all day long. Just find yourself a decent pair of espadrilles or loafer come the summer months and you’ll be all the more stylish for it:

G.H. Bass Larson Penny Loafers

The ultimateorthopaedic shoe that, quite frankly, is so awful looking it shouldn’t be worn by those who do need them, let alone the masses that don’t. If you want to look like an octogenarian who’s had innumerable foot operations, go ahead. If you don’t, just buy yourself a proper shoe, they’re not that uncomfortable, the rest of us manage just fine.

Wear these instead:

Reiss Ox Blood Longwing Leather Brogues

Your may see a theme here, footwear that’s a mix of two shoe styles should be resigned to a special place in hell – and the wheelie bin. These are the kind of shoes your mum got you to appease primary school dress codes so that you’d wear smart, and I use that word in the loosest possible sense, shoes and still be comfortable running around a playground. As an adult, dress codes aren’t that much of a burden; you can (hopefully) tie your laces, running around the playground isn’t on the agenda and your mum shouldn’t be buying your footwear.

Wear either a trainer or a shoe, make your decision and live with it:

Converse Jack Purcell Trainers

The opposite of the square toe and yet we run into the same problem. These aren’t the natural shape of your foot and they’re criminally atrocious in every way possible. No shoe has gone from being cool to a calamity quite as quick as these. Now the reserve of dodgy estate agents and real-life elves everywhere, of which you are neither. A good Chelsea boot or monk strap will serve you infinitely better:

Grenson Declan Suede Chelsea Boots