Cheap shoes that cost a lot

Media training the other day involved a nice suit, highly polished shoes (not the ones in the picture) and some rain. The rain told me that my shoes were letting in water around the sole. Of course I had to keep a fixed smile the whole time.
The thing is, these weren't cheap shoes. I'd paid around £99 for them and only about a year ago. Looking at the way the sole has gone, around the toe, they're not going to be good candidates for repair (and anyway my local repair place just glues new soles on rather than puts them on properly, I've spent two lots of £25 on a repair that lasts a matter of weeks and I'm not doing it again). So it looks as though it's new black shoes time.

And I'm going to spend some decent money on this. My previous formal shoes were from Church's - you know, you walk past it on Regent Street and wonder why anyone would pay £250-£300 for footwear.

Loake Chester II Tan

Here's the thing: the previous pair, which cost £225 or thereabouts at the time, were bought in about 1991 and I replaced them around 2006, with another £99 pair (I had a family by then and didn't perceive £200+ as affordable). So the maths goes like this: You spend £99 a go on two pairs of shoes since 2006, one lasts three years and the other one, call it an average of two years. That's near-as-dammit fifty quid a year. The £225 models lasted 14 years and were only put out of action by accidental damage. That means, as long as you spend actual money rather than bury yourself in a credit card, you're spending a figure just north of £16 a year. Now tell me which are the expensive shoes.

It still takes a hard swallow before spending that sort of cash up front on a pair of shoes, rational though it might seem, so I've been looking at alternatives. The people at rubbersole.co.uk have been in touch and invited me to check their service out; I can confirm that on placing an order a pair of Loake Chester II tan brogues (pictured) arrived within 24 hours by courier. These are £120 a pair and importantly in my case they have a thick sole, so if you walk heavily and wear out heels, toes or soles quickly these will stand up to it. Loake has been around for a while and knows how to attach the sole firmly unlike some cheaper brands. The website has a selection of shoes for more formal wear, sportswear, deck shoes, boots, loads of leading names and has a real time indicator of whether something is in stock.

Naturally I'd have opted for a black pair if I'd known my existing ones were leaking but you can't know everything. Tan's a good colour and seems to be coming in for a revival this autumn; the pictured brogues look good and are wearable with a blue suit or indeed jeans. Try to match them with a belt if you can - apparently Rubbersole tried selling matching belts a while back but found men preferred to buy belts in person, shoes online (which is odd as you're much more likely to find a poorly-fitting shoe if it's a brand you haven't tried before).

Meanwhile I'm going to have to buy businessy shoes sometime over the next few days or weeks. I can see myself spending quite a lot; I seem to use up more money when I don't.