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I have somewhat oddly shaped feet; They're very wide and my big toe on either foot points slightly inwards. Shoes with pointed toes generally cause me a lot of pain, so finding a road shoe has been somewhat difficult.

Typically, I buy shoes that are slightly too big, and I'm wondering how this will affect cycling shoes. I'm looking at a leather pair that has an extra inch of room in the toe, and lacing them up very tightly seems to do the trick for now, but I'm worried they'll stretch with time and become too big to hug my foot tightly.

Has anybody had similar problems finding cycling shoes? Any recommendations for a wide-toed shoe, or some brand specifically known for conforming to your foot over time?

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You could decide that special cycling shoes aren't important. – Jay Bazuzi Oct 25 '10 at 0:23
@Jay I've heard nothing but good things about them and I'm quite interested in trying them out. – meagar Oct 25 '10 at 1:50
Are you planning to clip in to pedals, or do you just want a lighter, stiffer shoe on the bike? – Jay Bazuzi Oct 25 '10 at 6:04
@Jay I wanted to try clip-in pedals. – meagar Oct 25 '10 at 12:02
For the warmer months, you might have some luck with open-toed sandals. I have similar foot-size issues (extra-wide) and decided that special cycling shoes aren't important. – freiheit Oct 25 '10 at 17:03
up vote 6 down vote accepted

You should look at using mountain style Shimano SPD compatible shoes. In general, mountain shoes have a little more room and give and there are a lot of brands that are SPD compatible.

Keen has a line of cycling shoes and sandals that you can find at larger outdoor retailers like REI or many places online. I mention REI specifically because in the past I have ordered two sizes of clothing and footwear online and returned the one that didn't fit with no hassle.

My experience with Keen footwear is that the run a little wide all over and are especially wide in the toe box.

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Not sure that cycling shoes that are an inch too long would work, the reason being is that your foot would end up pressing down with your toes instead of the ball of your foot, most shoes have some room for adjustment but its measured in millimeters not inches.

A quick google found this site: they may be able to accomodate your need, although I dont know how much they will cost!

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Looks like they start at $725 – freiheit Oct 25 '10 at 20:04
More money than I have to throw at shoes, but thanks for the suggestion – meagar Oct 25 '10 at 20:46
+1 for mentioning the position of the cleat; I wasn't thinking about that, but I am now. – meagar Oct 25 '10 at 20:53

I wear bontrager street shoes. They fit me OK, and I have pretty wide feet, and they also come with customizable insoles from esoles. The standard insoles seem to be fine for my feet, but if you have more specialized needs you could get a fitted set (I'd imagine that might cost a lot though). They offer a decent compromise between speed and comfort for me. Also I can walk around in them which is a bit practical advantage.

So I'd give these a look (if you can find any, I don't think they're very widely sold)

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Looking at the write-up for these, you can apparently place them in a conventional oven to make them pliable enough to be moulded to your foot shape.

I imagine shoes of similar material/build quality will allow the same method.

Not cheap though!

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