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Search For High Heels That Don’t Kill My Feet

I’ll be honest.  I’m a tomboy and I dress like one.  As a kid, I stopped wearing dresses/skirts because it was hard to run around in them without showing my undies or scratching up my knees.  By the time I was in high school, I owned lots of boy’s clothing and regularly dressed like a boy.  I just didn’t understand why girl’s jeans were so tight everywhere!

In college, I slowly transformed my fashion so that I was wearing clothing for my gender again.  Thanks to one of my trendiest best friends, I learned how to shop for clothes that fit me properly, and also how to put on makeup without looking whorish or stupid.

Over time, I’ve slowly phased out all my men’s clothing, but I still prefer simple jeans, tees and converses.  I do own about 2-3 dresses, all of which I only wear when I’m attending a wedding (or some other important life occasion) or make it out to a Hollywood club (which is extremely rare).  I have several pairs of high heels of all different heights, but I hate wearing them all.  That’s right, all of them!  Why?  Because they all make my feet hurt.

Here are my most recent 6 pairs of dress shoes. 5 of them are heeled, 1 of them are flats. All of them hurt my poor feet.

I may be slowly coming around to trendy feminine fashion, but I feel like high heels is the one category of female fashion that I just can’t figure out.  It’s odd because my mom wears tons of high heels and I grew up watching her wear all these sexy heels.  Unfortunately, I was never able to benefit from my mom’s extensive collection since my feet are way bigger than hers.  So, over the years, I’ve been trying out high heels for my 8.5 sized wide feet at lots of discount shoe stores hoping to find one that seemed mostly comfortable.  And over the years, I’ve bought quite a few that felt quite do-able in the shoe store, but then became horribly torturous to my feet when I actually wore them out for longer than 30 minutes.  I can’t count how many times I’ve gone out trying a pair of new heels, and then hobbling back to my car feeling like my feet are about to fall off.  Even my latest finds, a pair of trendy Naturalizers, caused me to have a huge blister on one of my toes.  What am I doing wrong??

Here you can see all the differing heels each shoe has.

Maybe I wasn’t made to wear high heels, maybe I’m just not buying the right shoes?  Maybe all women suffer aching feet when they wear heels but don’t mind the pain?  Maybe because I’m Asian, my feet are the wrong shape for western high heels?  Whatever the reason is, I’m at a loss, and I’m ready for someone (anyone!) who knows anything about wearing high heels to teach me a thing or two about it.  So I’m reaching out to you, my awesome readers, tell me all you know about high heels and where I can get more information on finding the right high heels for my large un-Cinderella like feet!

I guess I only like buying black shoes. I’m still not sure what to do with shoes that are not black, can you wear them with any outfit? And yes, those are my freakishly un-Cinderella sized feet.

How do I find a pair of high heels that won’t cause harm to my large wide feet?  Are there heels out there that look sexy and are comfortable?  Do buying more expensive shoes make a difference?  What are the best brands for both sexy and comfy heels?  Do I just need to suck up the pain for my fashion, or is there a better way?  Please, someone help me figure this thing out!

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