I’m a flats girl; I only rarely wear heels. I like the idea of heels, especially really high heels, the kind that make your legs look eleven miles long, but in my everyday life, there’s too much running around and hauling of laundry and tossing of baseballs to make a nice pair of stilettos a viable option. Most days, I opt for ballet flats, because they’re easy to wear and they go with my skinny-jeans-and-a-tee uniform and I can haul $200 worth of groceries in from my car without missing a beat.
But sometimes, even on grocery day, I want something prettier. Especially on grocery day, actually.
Last fall, I bought a super cute pair of argyle ballet flats, on sale! Of course when I got them home I realized that the reason they were on sale was because the print didn’t match up on the shoes, and they looked … odd. So I returned them and instead opted for a beautiful pair of turquoise-blue BCBG patent flats. And yes, even in the store I could tell that they were a little tight, but they were so pretty, and they had the cutest little silver-tipped bows on them and for heaven’s sake they were flats, how uncomfortable could they be?
Agonizingly uncomfortable, as it turned out.
Every time I wore the turquoise flats, I got compliments; the color was stunning and the shoes were really beautifully made. I tried to overlook the fact that after an hour in them, I wanted to hack my toes off with a dull knife, but eventually there came a day when I couldn’t take it any more. Those shoes hurt, and no amount of cute was going to change that.
I gave them to a friend. “I don’t care what you do with them,” I told her, “but don’t give them back. They’re horrible.” I knew that if I kept them in my closet, I would just keep wearing them, because omg so cute! But I’m too old to torment myself with painful shoes.
(Although honestly? I kind of miss those flats. They were so cute!)
((See why I had to give them away?))
Your turn: tell me about the most uncomfortable pair of shoes you’ve ever loved. Are you still wearing them? Or are you just admiring them from their perch in your closet? Ree and Kelly are gearing up for the third installment of the Putting it All Together video series and they want to hear about your shoes. So dish.


34 Comments so far
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I have a pink pair of heals, I call them my “barbie shoes”. I love pink. They are always uncomfortable and hurt all day, but I get so many compliments. One I stuffed them way up high in my closet so I am not tempted to put them on without a lot of effort of a step-stool to reach them. They are next to the ice skates I haven’t worn in over 10 years, but need them right?!? I have replaced my pink heals with a pair of pink flats that “fill in” just fine.
By Sarah on 04.26.10 11:22 am | Permalink
I am currently WEARING my most uncomfortable pair of shoes, which is the saddest thing ever. Even getting up from my desk to get a glass of water from the kitchen is agonizing, but they’re SO CUTE I don’t care. They’re beige and patent with a super high heel, an ankle strap, and the most adorable ruffly bits on the front of the toe. Made by Steve Madden who I feel certain is trying to kill me.
By Nothing But Bonfires on 04.26.10 12:07 pm | Permalink
I am actually nursing some injuries right now from my most uncomfortable shoes. And they are flats as well. Little silver, faux snake skin flats with a tiny bow on the front. I loved that they went with everything and that while they were super girly they had a bit of an edge. They felt fine when I tried them on and feel fine the first 35 minutes of wear. On the 36th minute the torture begins. I should have given them up after the first or second time they hurt me but I’ve had them for three years and worn them countless times always with the same result.
This last time I wore them there was blood. Blood from my poor, sad, raw toes!! I think it is time to let go.
Probably to the garbage, because one can’t really give someone a pair of shoes they have bled into, there is something disturbing about that.
By Hip Hip Gin Gin on 04.26.10 12:29 pm | Permalink
So funny you posted this today, because I just bid my most uncomfortable pair of shoes farewell. I had the cutest patent mary jane heels that I have worn and worn and received many a compliment on. The heel height was perfect, but the toes, oh the toes. I have been going through my closet section by section this last week and finally came to the black heels section. I tried every pair of shoes on and left these for last. After standing in other heels that were just as pretty and loads more comfortable, I decided I just can’t do it anymore. After putting them in the donation bag it was kind of a relief. I don’t have to try to work them into the rotation anymore and torture myself. There are pangs of fear, “Did I do the right thing?” etc. but my feet will thank me later…and they are only shoes. (Sacrilege, I know.)
By Allyson on 04.26.10 12:44 pm | Permalink
Ok, in all honesty, I put those flats on today and wore them around the house while I was getting the kids ready. When it was time to leave I opted for my other flats. The ones that don’t KILL MY FEET.
But DANG, they’re so cute!
(and FREE! Thank you!)
Oh the dilemma.
Susan says: HA! I’m glad it’s not just me. (Sorry about giving you hurty shoes. Will do better next time.)
By Rita on 04.26.10 1:31 pm | Permalink
OMG So cute! I completely understand why you had to give them away. I don’t have any current shoes that kill me. I have a couple of pairs of higher than normal heels, but they don’t hurt I just shouldn’t run to try to catch an airplane or something in them!
By elz on 04.26.10 1:36 pm | Permalink
Not blessed with happy feet I finally gave up the battle, got rid of anything that pinched poked or pained me and that left me with… crocs! I don’t care that they’re ugly. My feet have never been happier or pain free. I love the maryjanes the best but also have other styles. I don’t wear anything else. I even wore them to the opera. Life’s too short to have sore feet!
By Kris on 04.26.10 2:45 pm | Permalink
Yup. Just bought a pair of super cute 4″ black heels from Nine West. Peep-toe, combination of smooth and aligator-stamped leather. They look great, but are definately NOT 8-hour shoes.
By Danielle Walker on 04.26.10 3:05 pm | Permalink
i am a HUGE flat lover! love love love the flats. i have like 30 pairs.
so of course the worst shoe ever were these cute summery wedge sandal that are like 3 inches - i.e. 3 inches TOO high.
i couldn’t bear walking very far in them and made a very smart pit stop to buy some cheap flops for the remainder of my walk home.
so they sit in my closet. not really sure why.
By kat on 04.26.10 3:17 pm | Permalink
Those are adorable. Perhaps you can find a more comfy replacement?
My most uncomfortable pair were peep toe, 4-4.5 inch heel, Jessica Simpsons that I bought a full size too small because they wouldn’t stay on my feet otherwise. They looked great, but they only fit when I was standing still and they hurt after about 5 minutes. I wore them from like 3 p.m. to 11 p.m. for our rehearsal dinner and never wore them again.
By Kaleigha on 04.26.10 4:00 pm | Permalink
I had a pair of black patent leather stilettos that were a 1/2 size too big and v. v. uncomfortable to wear, but looked FANTASTIC. So fantastic that I bought them by telling myself that since they were on sale, and they almost fit with bare feet, they’d be fine. I’d be fine. I wore them twice, I think. And one of those was around the house to see how they felt.
I kept them for about 12 years before I finally realized that I would never wear them again [even around the house] and should give them to someone who could wear them without wondering if they were going to snap an ankle.
I still miss them.
By Suniverse on 04.26.10 4:52 pm | Permalink
These: http://www.flickr.com/photos/jenncanzo/2027180694/in/set-72157602830897440/
They’re fantastic, I KNOW, but they were a little snug before I got pregnant and my feet grew (sob), so you can imagine the snugness level now. I still have them. I WILL NEVER PART WITH THEM. But they’re now my walking down the hall shoes and that’s about as far as I can stand to be in them.
By Jennie on 04.26.10 4:55 pm | Permalink
Toe thongs. Can’t do ‘em.
The most uncomfy shoes I’ve ever loved? An adorable pair of lame (as in the gold shiny fabric) flip-flops, a gorgeous pair of fake-turqoise embossed sandals, a pair of lace-up greek sandals — any flirty sandal with a toe-thong. My poor feet cannot abide anything between my toes. Always blisters, from plastic to fabric, but I keep trying!
By Lisa Stone on 04.26.10 4:56 pm | Permalink
You know what’s really sad? My most uncomfortable pair of shoes are ballet flats too! Hot pink with a leather flower on the front. They’re darling, and I succumb to wearing them for short periods of time because of their hotness. Dumb.
By Petit Elefant on 04.26.10 8:00 pm | Permalink
I have the most adorable pair of leopard print Steve Madden flats. They look so great on and hurt so bad. I talk myself into wearing them whenI know I am only going to walk a little bit. It is sad really. Why oh why do I do this to myself over shoes? I am normally such a sensible person.
By juliea on 04.26.10 8:02 pm | Permalink
I bought a pair of knee-high black leather boots, half a size too small, because I had been searching for boots that would ZIP over my calves for about a year. I even bought leather stretcher, thinking I could make them fit. And then I made the mistake of wearing them to my job at the time, which was in a retail clothing store.
I have never felt such great relief as when I took those boots off in my car after work. But… they zipped. I still can’t find boots that fit, and this was 8 years ago - the wide calf ones are too wide!
By Michelle on 04.26.10 10:18 pm | Permalink
I bought a pair of gorgeous Charles David dark cherry red slingbacks on super sale from Amazon. They appeared to be the perfect shade of red. Patent red!!! Beautiful, but OH SO PAINFUL. There was a reason the $250 pair of shoes were marked down to $26. OUCH. Still in my closet however, since I can still wear them to work because I mostly sit at my desk all day. But, honestly? I rarely wear them. OUCH.
By BethanyWD on 04.26.10 10:40 pm | Permalink
I have a a pair of Pair of red t straps that have ruffles down them that are a little too tight.
By Bobbi Janay on 04.26.10 11:45 pm | Permalink
Aside from when I was little and grandma would buy my those shiny black shoes that were hard, which would have my feet so sore and blistery before we got out of the department, most of my shoes actually work for me. Some will hurt my feet if I’ve walked more than usual (say an extra trip across campus) but most have broken in with time.
However, there was one pair of striped flats that were so adorable and brand new. They started hurting my feet before I even got off my block, but I kept walking to campus. I’d momentarily stop to fold the heel down, try this or that readjustment. When I got there (3/4 of a mile later), I had to put on 4 or 5 bandaids to cover the sores. Then I walked home (all 3/4 of a mile) barefoot because I couldn’t do the shoes any longer. I got rid of them.
By Lori on 04.27.10 6:54 am | Permalink
I’m tall - 5′9. When I was single I wore a lot of flats because I didn’t want to invest in heels in case the next man that came into my life was short. There is nothing worse than having heels you can’t wear because your boyfriend du jour is the same height as you. So when my husband, my 6′3 strapping firefighter hottie came into my life, I headed to DSW at warp speed and literally replaced my shoe wardrobe. I was going to wear stilletos to the grocery store - BECAUSE I COULD! Turns out that my high school knee injury didn’t really like heels though. After a year of being in denial about every single shoe in my closet, I gave up the jig and went back to flats. But I kept the tall hottie husband.
By Pamela on 04.27.10 5:02 pm | Permalink
I once bought a very cute pair of shoes that hurt like heck, but I couldn’t return them and kept trying to wear them because I couldn’t admit that I’d wasted my money.
When I got a puppy, those were the only shoes she chewed up. Good dog!
By STL Mom on 04.27.10 6:03 pm | Permalink
I USED to have a gorgeous pair of BCBG black patent, peep toe heels. They had darling bows on the toes. They looked fabulous and hurt after fifteen minutes. Funny they were the only shoes my boxer has ever chewed. I wasn’t sad.
By andrea p. on 04.27.10 9:09 pm | Permalink
I USED to have a gorgeous pair of BCBG black patent, peep toe heels. They had darling bows on the toes. They looked fabulous and hurt after fifteen minutes. I wasn’t sad when my boxer chewed them up.
By andrea p. on 04.27.10 9:11 pm | Permalink
Sorry Susan. I didn’t mean to post twice.
By andrea p. on 04.27.10 9:15 pm | Permalink
I have a pair of glittery gold 4″ peep toe heels that I bought for a Christmas party one year… I don’t know how I made it through the night (a little bit of alcohol would be my guess) because I’ve tried them on since then and it feels like the peep toe is made of razor blades! But I keep them anyway because you never know when you’re going to need 4″ gold glitter peep toe heels!
By Danni on 04.28.10 7:37 am | Permalink
A few years ago I bought a pair of nude colored suede wedge espadrilles. They were so flattering to my legs. I wore them to the farmer’s market with my boyfriend. As I browsed fruit ahead of him, I was aware that they were hurting the tops of my heels, but I figured they were just breaking in. When I heard him ask if I was OK in those shoes, I looked back there and saw BLOOD! Major blood on each side, staining the shoes, and my chewed up skin was sticking out of the top.
By Kelley on 04.28.10 3:14 pm | Permalink
I had some black heels that I thought were semi-uncomfortable, but cool, so I wore them to see “The Producers” in NYC, only to discover that walking in them for any length of time would cause skin and blood loss.
By Susan on 05.05.10 11:25 am | Permalink
I have a pair of platform sandals that look good but I haven’t worn in ages because they kill my feet. They are collecting dust in my closet.
By Mami2jcn on 05.11.10 8:42 am | Permalink
I bought the COOLEST pair of shoes with the craziest pointed toes and wildest bright stripe colors you’ve ever seen. They were fine when I wore them in the city at work, but, when I wore them to a suburban book club one evening…they ended up being very uncomfortable after they got mocked!
By Kim on 05.12.10 3:10 pm | Permalink
The most uncomfortable shoes I’ve ever worn were heels that were 3 inches high and thin - and no, they went back to the store! I thought I could handle it but I couldn’t!
By Jill Hayes on 05.14.10 4:27 pm | Permalink
The most uncomfortable shoes I’ve ever owned were a pair of linen & gold trimmed flats, which pinched my toes, the sides of my feet, and my heels. Basically everywhere. But I still wear them
By Ashley on 05.14.10 7:55 pm | Permalink
I had the cutest pair of white leather boots. Unfortunately they were very pointy and my foot is not : (
By momznite on 05.17.10 9:06 pm | Permalink
I have the cutest pair of red heels. Sadly they just sit in my closet because they are so uncomfortable!
By kristi on 05.18.10 11:21 pm | Permalink
I hate flip flops, I just can’t wear them. I no longer even try, I there are so many cute sandals I don’t need them.
By Anne on 05.22.10 6:04 am | Permalink
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