Pointe shoes were also my most uncomfortable shoes in my youth. I never did horrid high heels. But I certainly wore flats with zero cushioning, etc. I don't remember them being dreadfully uncomfortable though, maybe it was just the comparison to the pointe shoes that made them seem okay.

As a stay at home mom, I now walk a ton--as much as five miles a day. And I am very, very, very particular about shoes being comfortable and will sacrifice fashion for comfort every time (though I still refuse to wear tennis shoes for anything except walking the dog and working out).

TorontoGirl, you are cracking me up!
I think I'm more in Gigi's boat--more inclined to try less comfortable shoes now than I was when I was younger. It's not so much that I didn't go for style--I did! But I liked clunky styles, mainly because I felt they balanced my calves, which were always pretty big and muscular looking in relation to the rest of me. Now I'm gravitating toward some more refined looking styles and narrower heels. And I'm wearing heels more often, because I like the feel and look of being a little taller.
I've always had a low tolerance for foot pain, though--at least when I've had a choice. This thread reminds me of the timed 13-mile road marches I had to do during one of my assignments in the Army. I always wore my most comfortable combat boots, two pairs of socks, vaseline, you name it, and I still ended up with heels that looked like hamburger when we were finished. I'd go to the locker room, shower, bandage up my heels, put them back into a fresh pair of combat boots and go back to work!
Oh, and I do recall Candie's. I never had a pair, but oh, how I admired them. I loved Dr. Scholl's sandals, though, and wooden-soled clogs. And some pretty odd-looking but oh-so-stylish Bass kiltie-loafer-looking shoes with a weird shaped rubber platform. I really loved those little babies in my preppy-wannabe days.

I was very pigeon-toed as a child. In 6th grade, I became enamored by the Scholl's wooden "Exercise" sandals. When my toe didn't track in a straight line, I would hit the opposite ankle with the wooden front of the sandal. Yowza! I would wear through a pair every summer. I'm no longer pigeon-toed, but I still have faint scars on the inside bones of my ankles!

Bwahahaha, nancylee! Lovely, if not painful, story!

While in Palm Cove last year I saw a wedding party with more than one young gorgeous thing limping in heels. I think heels look awesome!....... But NOT if you are limping. Whip them off and go barefoot (we're talking 20m from the beach) or let no-one know that you are in agony.

Mr. K loved to buy me sky-high heels, preferably with platforms. Many of them were ridiculously painful, but he didn't seem to understand that so I wore them out on dates with him and grinned and bore it.

After I ran away from home last year I donated every single pair of painful date shoes!!

Oh yes - painful shoes... weddings and parties. Awful! A few years ago, I was a bridesmaid at a wedding and my bride friend bought all of us matching strappy sandals to wear except for one of the bridesmaids who flatly refused to wear heels. Most agonising night ever! My feet took days to recover from the blisters where the straps cut into me.

I have always worn high heels and still have a few pairs in my wardrobe today. These are mainly for "sitting" sessions but I love kitten heels for shopping.

As I am 5 foot 1ins I need a little bit of extra height so platform shoes have always been favourites. The Queen Mum and Princess Margaret wore these all their lives as they also were vertically challenged.

Peep toes were always a favourite until about eight years ago when I had to have a pin fitted into one toe and as a result it is shorter than it should be. I hate that so my sandals tend to be closed in now.

I did wear Scholl sandals and they were certainly clumpy but surprisingly comfortable. I only gave up on these when my neighbour's dog ran off with one on to the heathland around our homes and I never saw it again.

For around the house I now wear FlyFlots and these are the MOST comfortable shoes I have ever worn. They are safe also as the soles grip so well even on slippery surfaces. As a result, however, my other shoes feel unsafe and I find myself looking forward to slipping on my FlyFlots again.

It's funny, I never made it much of a habit to wear uncomfortable shoes, even in my youthful foolishness. I did , however, succumb to the pressure of a last-minute shopping effort for my 40th birthday (hubs surprised me with a trip to NYC including a wonderful dinner and a helicopter ride over Manhattan). We had shopped for an outfit for me -- black wide leg trousers (I still own them), and a very cool corseted top with a filmy semi-sheer layer that got belted over top (it was borderline too small then, and definitely too small now, but I keep it even though I don't think I'll ever wear it again -- quite the boobalicious look!). But when I went to look for shoes, noting seemed to be working. I ended up with a lovely strappy pair of Pliner high-heeled sandals, but they were half a size too big, which means my feet were sliding down all night -- the straps were killing me and the heels felt so high. There are few times I've been so relieved to take off a pair of shoes! I sold them on eBay a couple of years ago.

Oh wow, ladies. LOVED reading about your peds. I am laughing and crying at these stories. Our poor feet.

I don't ever remember not having bunions (my Mom and Dad both have them) but luckily my toes don't cross or overlap. Having started running at 13 and benefitting from a great coach who drilled foot hygiene, I generally stayed away from dumb shoes. Flats with a good sole and half inch heel are my favourite, but I like a dressy heel or work pump. I'm a leather snob too.

My recurring foot mistake is sales goggles and limited sizing. I won't go smaller than 9.5, but too many times I've picked up that cute size 10 only to end up passing it along soon after.

In high school, a neighbor passed down to me these totally awesome navy suede clogs that she'd worn in the '70s. The soles were basically giant, heavy blocks of wood, so they were really hard to walk in. To top it off, they were a little too big and they were, well, clogs, so they kept sliding off just enough that I'd go and put my foot down hard on the edge of the (stiff, wooden) heel.

My one pair of dressy shoes in college were the black high-heeled Steve Madden mary janes that seemed to be everyone's one pair of dressy shoes in the late '90s. They probably weren't as bad as they could be, but, since I never wore heels otherwise and since they were really stiff, pinchy leather and had the strap for yet another place they could rub weirdly against my foot, trying to do even basic walking in them would pretty much make me want to cry.

In general, I try to buy reasonably comfortable shoes now, but I'm really bad at giving up pairs that are less comfortable than I think they're going to be.

Oh my gosh, Eirlys, your story reminded me that my dog chewed on a pair of Dr. Scholl's I had in my closet. Good thing I was pretty much done wearing that style!

Yes! Those flatform sneakers in the 90's my arches which are really high fell wearing a pair of those. I also had a pair of pointy toed ankle boots that hurt everytime I wore them. I'd go out dancing wearing them and spend the entire night sitting rather than dancing.

I have no such patience for that crap these days. Especially so since I am primarily interested in comfort and having cute feet for summer sandals. As a result no matter how cute the shoe is there is no way I'm buying it if it is not comfortable from day 1.

Wow, I didn't knew I'll have a story to post here, too. I realized it only when reading BethAnn's comment. I wasn't peageon toed, but 25 yrs.agö I've had the same kind of wooden sandals, and...OMG---hilarious! Not kidding! LOL!!!I've even got to the ER having cut into my flesh on the inside foot under my ankle with the raw edge of the oposite leg's wooden sole. I still have the scar from sewing me up there:-((.

Well... 20 years ago my mother was still dressing me, and I don't remember much about my shoes.

In my teens (~10 years ago) I remember trying to squeeze my feet into size 10 and 11 shoes because size 12s that were appropriate for a teen were impossible to find. That was a bit painful...

I guess I am lucky that I found YLF early on in my adult fashion life because I ONLY wear comfortable shoes now and forever... cannot sacrifice comfort for anything! So no interesting stories from me.

Aubergine, I probably had those same Steve Madden mary janes in the 90s - my only pair of heels. And I thought my feet were a size bigger than they are, so they were horribly uncomfortable. I spent my teens wearing boys' sneakers and had no idea what size I was when I bought my first heels in college. At least those mary janes had nice chunky heels for stability!

Cocolion, I do Irish step dance which is all done in demi-pointe as high as possible. I think you're right that dance can sometimes make it easier to wear heels - it's made my ankles and arches very very strong. But it's also damaged my toenails and caused lasting pain in the ball of my foot (where all my weight rests). So, when I wear high heels, they're comfortable in the moment but I have to avoid wearing them often to give my metatarsal joints a rest!

Ha! I had those Steve Madden mary janes too! They were SO heavy and so badly designed. I remember my toes sliding all the way forward when I walked so they slammed against the fronts of the shoes every time I took a step.

Also:
http://www.buzzfeed.com/leonor.....et-your-ey

I owned an embarrassing number of these in the 90s.

Diana, that link is so funny - at least half of those styles are all over the stores right now as the 90s resurgence continues!

As for heelies or wheelies or whatever they're called, one of my quirky cool friends has been wearing them nonstop since the 90s and she is finally out of replacement pairs. They discontinued the adult sizes a while ago but she'd been buying backstock or off ebay. The end of an era...

Diana, that link was hilarious! I think I had those exact Mia sandals, plus a bunch of the foam flip flops and some canvas mary janes. And a lower version of the elastic slide sandals, which were actually incredibly comfortable. I just remembered one of my pairs of foam flip flops actually broke when I was walking back from somewhere -- the toe part came unglued or something.

Ah- uncomfortable shoes!
Just yesterday my DD wanted to wear shoes other than sneaks for Church, so she chose a pair of mine I had put in her closet and no longer wear.
As it turned out, even with in-soles they were about a 1/2 size too big.
She was hobbling from the car to church, the service had already started, what a kerfuffle!
Into the donate pile they are going along with another pair I thought I might wear again. But- they are from my inexpensive, synthetic shoe-purchasing days. I gave them one last try and was reminded how important it is to buy comfortable shoes.
'Cheap and Cheerful' is often 'Cheap and painful' !

When I was 22, I sprained my ankle while wearing 3" red patent leather pumps. I had to wear a surgical shoe for about 6 weeks, and flats for another 6 months. Finally I tried heels again, and immediately sprained the same ankle. My ankle was so weak I sprained it 2 more times, once while wearing flats.

That was so long ago I cannot remember which ankle it was. Now I wear shoes between 1/2" and 2", with absolutely no exceptions.

Where is a like button when you need it for MaryK's comment about running away from home and donating all of her uncomfortable high heels?!

When I lived in NYC I walked everywhere. I think in summer I single-handedly kept Band-Aid in business. When feet sweat without socks, things rub! Luckily in NYC there's a Duane Reed drugstore in every corner, so I'd hobble in, buy a box, strap them on, replace them when they peeled off. Very glam. Finding the perfect NYC summer sandals that didn't hurt, rub, stink, or break was a Sisyphean task. Really the only thing to do was to alternate pairs so at least you'd get blisters in new places. I think I should have just worn sports socks and sneakers to walk and swapped for cute shoes at the office like all the fashion misses, but it seemed too silly to keep my entire summer shoe stock at work, plus, what if I needed a certain pair on the weekend? So I suffered.

Diana, that was too funny! I had a version of #1 and #16.

15-20 years ago was HS/college for me, and I was firmly in practical mode at the time. No impractical heels. Also, it was the 90s, so there were plenty of Docs and Vans and Birkenstocks to go around. Fast forward a few years, though, and I had my own share of impractical shoes. I've never been able to walk comfortably in super-high heels, though, so 3" was as crazy as I got.

My favorite shoe-related fail of recent years was after I'd lost weight last year, and I lost about a half size in my feet as well. But I hadn't tried my fancy shoes in a while so I didn't know it. Took transit to a symphony concert and I barely made it from the station to the concert hall and back. I was this close to asking my DH for a piggyback ride.

Bass penny loafers in junior high. Everyone was wearing them, and I begged for them. My feet literally bled repeatedly when I wore them. I had band aids all over my feet. Haven't bought another pair of shoes from bass since then, but I wore those penny loafer to pieces.

My Docs in the 90s killed my feet until I broke them in. Again, more blood shed.

Late 90s I fell in love with 3inch + high heels. But they were chunky and square toed back then, so they had to work, right?!?

Injured my back in 2001 and was told no more heels. Ever. So, I broke up with cool shoes for a long time and settled for whatever drab ugly shoes had a low enough heel and enough cushioning not to bother my back. Then I found YLF and have slowly come to realize comfortable shoes don't have to be frumpy.

Ladies, thanks for all the laughs! This thread is really taking me back. The time frame of 15-20 years, however, catches me at my most sensible, strangely enough. I had lots of loafers and flat shoes from working in a bank, when I needed to stand all day, and in another job where less dressy attire was required. It was a time of Aerosoles. They weren't really what I'd wear on my own time, though.

I too did the pointe shoe thing. Once I realized how torturous it was (and I already had the beginnings of what would become monster varicose veins-imagine!!) ballet became less of a priority and faded into the past. I did have a pair of wood-soled clogs in middle school which probably were a fashion error, but I absolutely loved them. Their clomping (I thought) made me sound authoritative.

My most vivid fail happened only last year, and I'm still coming to terms with it. I got a pair of black suede flats to wear on a trip to Europe, but bought them a little too snug, thinking they'd stretch a little. I may as well have left them at home, since I avoided wearing them left and right. Just goes to show you've always got to be tough with yourself about what you put on your feet!

BTW, Dr. Scholl's is now putting out some pretty good footwear-I have a pair of bronze flats with a cute buckle, and a nude pair of chunky heels that are actually quite comfortable.

I am with Firecracker and Gigi - I got a late start to the game. I remember my grandma telling me once when I was about 18, how nice a little heel would make my legs look and I thought she was crazy! I spent my teens and twenties in flats and comfortable shoes, my early-mid thirties wearing heels sparingly, and finally in the past five years have occasion to wear them frequently. Now, in my forties, I still have a reasonably high tolerance for impractical/downright crazy shoes, but I am learning to wear them more strategically. I am also trying to buy better quality shoes and learn what things are deal breakers when it comes to comfort. Truth be told, though, I am still willing to suffer a little for the look I want. Only a little.