Do you remember the episode of Friends when Monica spent an obscene amount of money on new boots but then when she put them on they were the most uncomfortable shoes she had ever owned? Later in the episode she made Chandler carry her home on his back and ended up forgetting the shoes at dinner. She never went back for them.
I'm having that same problem. A few years ago I found the cutest slip on flats ever. I bought them in every color. They made it three years and finally died. So last year I bought a new pair of black flats. You guys they are the most painful shoes ever. They rub just above my big toe and they are so high in back they rub my ankle and make it bleed in under an hour.
See look how cute they are.
Here is where I become conflicted. I know these shoes hurt me yet I keep putting them back in my closet. I made it one hour today before my ankle looked like this.
Ouch. (Also lease note that my jeans are as always too long and end up dragging on the ground getting dirty, some day I should order jeans in short length)
So what do I do? Do I put them back in my closet again? Do I just throw the damn things away? I only paid about $15.00 for them so it's not worth it to put them on Craigslist. I could donate them, but I'm not sure I want to inflict this pain on anyone else. Is it going against the universal girl code to throw away perfectly functioning shoes? For now they are sitting by my front door. I'm worried if I put them back in my closet another month will pass and in a hurry I will think, "ooh cute black shoes lets wear those." Then an hour later I'll be crying like Monica. So tell me, what's a girl to do?
misguidedmommy.com 
My favorite part of this post is how you have to roll your pants 248 times in order to wear flats.
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I had this same problem last year. I have to wear flats to the office (because I am too tall for heels really) and my old black ones died a terrible death. So I bought new ones at Target for like $20 but the girl at the register warned me that they were so very cute but so painful.
The first time I wore them I had to take them off as soon as I sat down at my desk. I don’t walk far to get to my car and from my car to my office.
They probably just need serious breaking in. The bit over your toe and at your heel need to be soft and flexible so they don’t rub. I would take the shoes off and stand on the heel edge to crush it down and work out the stiffness. I would grab the edge by the toe and bend it and stretch it. I also put heavy things on it at home to smash out the toughness.
It is a bit of work but as I have trouble finding cute black flats and have to have them I did it. If you don’t have to or really want to, I would find new shoes.
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Honestly, since they were only $15 I’d trash or donate them. You could try putting on socks and wearing them around the house to get them broken in too…
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For 15 bucks, I’d ditch them and invest in some that don’t hurt. It’s not worth it – I’ve continued wearing a pair of Tory Burch flats I have because they are redic expensive and I just plain have to so I understand the dilemma.
PS My pants always look like that too (or I staple them for a quick fix which is also super classy.)
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LOL I completely understand, I have a pair of marroon suede high heels in my closet that are just a tad too small…they always have been, even when I first bought them, and I can’t for the life my me, throw them out even thought I think I’ve actually only worn them once…but they are the most awesome shoes I’ve every bought.
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