Yes, and no….
the boots below, 2.5 inch heels wearing and loving. The heels in the 2nd find are the same height but I tried them on to wear to Services at Rosh Hashanah in September and immediately took them off and switched to the dressy flats in find #3. Still holding on to a couple of my dressy heels, because I’m not sure I’ll never wear them again.

Kkards, those blue flats are adorable!

I think we all need to be real and evaluate our own personal comfort and health levels when it comes to our fashion and beauty choices, and realize that other people have other requirements.

When it comes to footwear, more than heel height, I have to be careful of anything that rubs or presses on the top of my left foot in a certain way. I dropped a drawer on that foot well over a decade ago and it’s never been the same since. Those adorable shoes that kkards posted would probably hit that old broken bone and cause me a lot of pain, while the heels she posts may not bother me at all because the tops are smooth. I encountered trouble with a lot of fashion sneakers I tried, because certain styles have ridges or bumps that press on that bone.

Like I said, heel height is only one of many ways a shoe can be good or bad on an individual.

I'm 73 and don't have a problem with higher heels per se. I don't wear kitten heels for the most part owing to the wobbliness of them but do have several identical pair of pointed toe ankle boots with those and they're fine. I have a house with a couple flights of stairs and can wear those to carry laundry up and down to the basement.

I prefer block heels or thicker heels. Boots are easier than pumps.
But in general I want either boots or ankle strap shoes or laced oxford type shoes, whatever the heel height. Otherwise, my foot will slip forward. I have some that are 3 inches and are fine, both pumps and boots. Otherwise I like 1 1/2 - 2 1/2 inches.

I believe I could walk miles in them but my experience is that the sidewalks tend to tear slimmer heels up so I don't.

ETA pic of ankle boots

I donated everything over 3.5 because they were not walkable but kept the rest. I find what is left comfortable — no need to hire a car service to get around town — and have no plans to sentence myself to a life in flats.

Vildly, to your point on ankle stabilization and lace-up shoes—that is definitely something my highest shoes have going for them. I tie the Oxfords firmly around my ankles, and they and my tall boots both provide ankle support.

The placement of the heels on those shoes is also just right for me. I’ve had kitten heel pumps before. The placement and angle of the heel were absolutely perfect for my foot/ankle/hips, so they felt very stabile and I wore them often. But if that isn’t the case, if a pointed heel, even a short one, is off just a little bit, wearing the shoes would be like balancing on a wobble board all day long—no thanks!

Oh, and on pretty low heels, I have velvet and metallic boucle loafers, and ballet flats and kitten heels in evening fabrics. And one random pair of ancient black leather kittens with a rhinestone buckle. I love kittens, they are a classic that works well with my wardrobe, so don’t at me about how they are dowdy. These are a mix of Butter, Cole Haan, Kate Spade and Stuart Weitzman, from years when I could find dressy low heels — nothing more recent than 2017. I love some of the recent embroidered suede and velvet slipper shoes, but have not pulled the trigger because I am set. Except for teal….

I’d like to add that for me the height of the heels is also determined by my overall style at the moment. I wore 3” heels with bootcut pants and jeans. I probably had only one pair of low heel shoes - winter boots. Everything else was with heels. When I switched to slim or cigarette silhouettes, I slowly fazed out heels.

No high heels in my closet, but I agree that they can look fabulous. The closest thing is a pair of EF1.5” heels. I do have dressy flats, mostly ballerina style but all are pretty old now. They should be replaced but I have not found anything. Most have some shine or sparkle. Ankle straps could add stability but none really fit my boney ankles to provide any help. I am ok with really flat shoes.

I've never been one to wear high heels. My preference now is even lower, probably max 2". I agree that if they have some ankle straps or other sturdy parts that helps. It definitely doesn't look elegant if I fall off my shoes! I also prefer a slight heel even in flat shoes but I'm not too picky about that. I'm pretty lucky in that my feet don't have too many limitations and are a common size - maybe that is why I love shoes

My sandals below are my "dressy" go-to's these days.

Robin, feet really are so individual! These sandals were going to be my everything shoes this summer. They are constructed similarly to both pairs you show, with an ankle strap that attaches to a little piece behind the heel. They are not raring successes. I can wear them sometimes, but whereas you say sliding off your shoes would be inelegant (I agree!) I feel that is exactly the risk with these, so they are relegated to very occasional wear for me. The tiny wedge is less than .5”, but I feel more secure in any of the shoes I posted previously.

I am not wearing heels higher than an inch or so, as I am most comfortable being short at all times, haha, but true.

I have worn them in the past though, and I agree with posters above that they can be very comfortable and non restrictive. I still think they look lovely and add polish.

SF - those are not my walking-everywhere shoes but for dressier occasions. But they don't slide around which would make a difference.

Back to say that pitch always plays a role on how I feel In a heel. And generally a Cuban or western heel is about the most comfortable heel I’ve ever worn, and I have some sneakers that are totally flat, and yet they are not comfortable enough for walking miles in. For example in the Finds below, the boots are better walking for days shoes than the sneaker, at least for me

Definitely kkards! Sneakers give me back and hip pain, but my normal 2 inch block heeled sandals and boots go all day with no issues at all. The cowboy boots I had some years ago were The Best winter walking shoes I ever had.

Kkards -- that's the thing for me, too. The pitch. My experience with the shoes you show would be identical. I can't wear the flat sneaker without an insole and even then my feet get tired by the end of the day. Whereas my feet would be fine in the boot you show. I mean, all other fit issues being addressed!

StagFash -- I, too, bought a propane stove even though I am against fossil fuels. We are indeed creatures of contradiction. When it comes to heels, though, I don't feel too much inner angst about them. There was a time when heels were for men. And a time when pattens were the only things saving your clothes from the gutters. And a time when heels were tools of the patriarchy. And now I think -- it's like makeup or any other form of adornment. Women/ humans can reclaim this stuff and have fun with it. Or not, as we wish.

While I tend to opt for lower heels more often than not these days, 1-1.5 inches, I still have plenty of boots with higher heels that I like and wear. The highest is probably 3 inches. I only have one pair of dressy shoes, with a heel height of 3.5 inches. I haven't worn them in a couple of years, but have no plans to get rid of them. They are super comfortable. Flat shoes I cannot walk in. They cause my low-volume, flat feet to cramp up. My feet feel immeasurably better in footwear with heels. Two inches is probably my sweet spot. As others have noted, it's not simply about the height of the heel that makes a shoe comfortable or not, it's the pitch and the last.

I was a devoted heel-wearer back in the day, but when I left the corporate world I also left those shoes behind, except for dressy occasions. As I've gotten used to wearing sneakers and things more often, my heel tolerance has reduced, and currently, my highest heels are 3", which I find add the dressiness and height without being wobbly. I think I am probably more concerned with the thickness of the heel than the height nowadays though ... whereas I wore stilettos until my 7th month of pregnancy 16 years ago, today I would rather do a 4" block heel than a 2" kitten heel, for example - feels sturdier.

1.5" to 2" heels don't feel too "heely" to me, so I wear these regularly ... for example my burgundy Blondos are 2" heels and are as comfortable as any other shoe I have (more comfortable than a true flat, I'd say).

I have hallux rigidus in my right big toe/foot which means I get almost no flex in that foot. This means no heels, even block heels and the like. I can go about as high as 1.25 or 1.5 inches.

DonnaF, how does hallux rigidus usually happen? After I broke my toe and foot, that’s what I was diagnosed with (a couple months later). Just walking in a slight heel brought tears to my eyes; holding my son’s hand made it feel better (hooray for oxytocin!). The doctor had custom insoles made for me that included a firm plate to protect that area from flexing. I wanted to regain the flexibility, so I refused to wear the insoles. The break was around May of 2020; my original goal was for my friend to be able to teach me tango. The toe still doesn’t bend quite all the way, but I can wear whatever shoes I want now and do box jumps. I’ll see my friend in a couple weeks, and if he’s ready to teach, I’m ready to tango. But I don’t know how other peoples’ feet get that way, so don’t know how generalizable my experience is to others.

Although I don't really consider them "heels", I wear platform sandals in warm weather.

I own literally ONE pair of (kitten) heels that I wear for every occasion that calls for them. Weddings, funerals, events where I just don't feel right wearing flats.

My weird feet, with wide toes & narrow heels, have lead me to Vivaia shoes which I'm in love with for many reasons. Washable! Made from recycled water bottles! Super comfy!

Most of my heals are for occasions wear, I am OK wearing them for a few hours and can walk/dance with a2 inch heels. I think I would need some practice as I haven't used them for a while.
I noticed that when my core is strong (= good posture), it is way easier to walk with high heels.
Strangely, wedges are a big no-no for me as they are not flexible enough and I find it more difficult to walk on them.

I won’t go over 2 inches, and prefer 1.5. I do like to keep one or two “dressy” heeled shoes around (well pre-COVID that seemed like a good idea). I did pick up a pair of AGL heels (still unworn) on deep discount in 2020. I find AGL very comfortable but the prices are ridiculous.

No more high heels, no way, no thank you. Flat shoes, sneakers, boots with short (maybe 1.5 inches) block/regular heels are all I’m wearing these days.

I have just checked and I have 3 pairs that I would call “high”. First two, 3 inches, one from 2010 and one from 2011, were not worn for some time but have been for Art Deco type dress-ups in the past. I am reluctant to let these go although I have since bought a genuine vintage pair of gold pumps and some black sandals with gold Art Deco style motifs to my eyes, which I have worn instead, both are much lower heels.
Then I have one pair of boots with 3-inch block heels, much more stable, new in 2017 but little worn. High cost-per-wear, I feel bad partly because those were largely from a gift voucher from my UK-based sister to my favourite shoe store. I enthused over the gift and the boots and don’t wish to admit a mistake.
No more 3-inch heels bought since then and I feel never again. I have found dressy boots and sandals with no more than one inch heels since.