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Depends on height.
First time I wore 4″ heels I struggled a bit.
It’s just a question of Balance, as the Moodies said.
3″ has always suited me fine.
Try not to put all your weight on the heels – but do watch the posture. It’s a body balancing act, and I’m sure a couple of extra kilos of silicone forms helps.
When your back is nice and straight and your gaze up and forward, a bit of momentum in the hips and backside out a little – the heels almost walk themselves.
It’s not the heels, it’s the toes!
If they’re slightly too narrow, you’ll find out halfway to wherever you’re going, and your feet will be raw by the end of the night.
Lovely, comfy, round-ended, wide-fitting court shoes I can shop in all morning.
But it’s trainers or pumps in the afternoon for my poor toes to rest!
Love Laura
I have been wearing heels in my crossdressing for many many years and can manage 5″ heels (no platform) with no problem. When we start getting into 6″ no platform heels then things start getting a little tricky. Much slower and much smaller steps. While I can manage walking in 5″ heels for several hours at a shot, but anything without a platform and higher than 5″ and I’m only good for a much sorter period of time.
Of course having a woman’s size 11 helps too. The arch is not so high in a size 11 compared to the same height heel in a size 8. Big difference.
Jessie
If I keep my heels under 3 1/2 inches I am fine, but any higher than that it starts to become an issue. When I think of a true stiletto, I think of something that is about 5 inches high. I have one pair of 5 inch heels, they look great but I am not going anywhere in them, they hurt to much. Remember to walk in your heels by letting the heel hit first, don’t walk in your toes. Enjoy!
Like most girls here I am comfy walking in three inch heels when out. Took lots of practice and wore them a lot around the house doing housework too. If you have learned to walk in 5 inch you will find the transition to a smaller heel so much easier. It just takes time and walk from the hips not the shoulders as guys do. You will love them after a while .
Technically I don’t have any stilettos of 5 inches but do have one pair of 4 inches. One of my first purchases but “oh my” was that a experience and now only wear them around the house and only when sitting pretty. Walking around well very slowly and not for very long. More show then anything. Maybe in time with practice. They do look awsome though. But 3 inch I’m good with and now quite comfortable but now learning more about kitty heels and of course flats. But still love hi heels and still do admire my 4 inchers as my wife calls them (bitching heels) lol….
Shoe’s aren’t they a blast….👠
Stephanie 🌷
I am such a bore……….you’d think a short girl would do whatever to be …..taller……….with stilettos…….but not this one………they hurt your feet………..maybe wreck your back……………getting a nice kiss from a guy………..I;d stand on a milk crate………or a few steps above on a staircase or stand on the running board of his truck…………………… I know………..Boo on Karley………….
Trouble? Did you say “Trouble?” What are you talking about? JK! Stilettos are my favorite clothing item, no contest. I remember in the 70s, they kind of moved away from stilettos and I was concerned. But there is something about traditional pumps, peep-toes, sling backs, and strappy sandals that does not quite do-it without stiletto heels – mostly 4 – 5 inches. So, they keep coming back. For all the things you read and hear about stilettos 👠 or high heels in general, I have found them uniquely easy to stand in, walk in, maneuver in, and even run in. Clunky heels of any height are really much more difficult and sometimes dangerous, particularly if they’re tall. Their propensity to land flat on the heel can easily turn your ankle. Stiletto heels allow the ball of the foot (sole of the shoes) to determine landing and let the heel come along for the ride. Strangely enough, most things you read about wearing heels seem to assume that women know more about wearing heels, but most of us know that is just not true. To many women, they might be just shoes. But for lots of men and women they are an art form or, as they say in 2020, they’re a thing!
FAM
I used to play ice hockey and I think that helped a lot with walking in heels. It didn’t take long to get the hang of it. I can walk in pretty much any heel up to 5″ without a platform – if the shoe fits well and is reasonably comfortable. Higher heels with a platform aren’t a problem either. I have a pair of 6″ Pleaser sandals with a platform that I’ve worn for hours many times.
Getting there won’t happen overnight. There’s no substitute for practice. Start with moderate heels, say 3-4 inches. Stand straight with your chin up and your chest out. Walk from your hips. Take shorter steps than you’re used to and land on your heel. Look at your destination as you walk.
Wear heels while you putter around the house. When you feel confident take it outside. That’ll be harder compared to indoor flooring. Stick to good, level pavement or concrete like you’ll find at a shopping mall or parking garage. When you can handle that you can graduate to uneven sidewalks and the like. Really irregular surfaces like cobblestone and metal grating are ill-advised anytime.
Strength and stretching exercises can help. Calf raises, toe raises, ankle rotations, and calf stretches are good for improving your walk in heels. Ice skating is good too if you’re up for it!
Good luck and have fun!
Emily
Hi Rosiebeth,
I love walking in stilettos! All 5+” if I can help it. Like the ladies here said practice! To Emily’s point, correlating it to ice skating helps, and in my case it was the ankle support. So my advice is to find a pair of shoes or boots that offer the ankle support first, learn to walk in them (heel – toe, small steps) and then move on to shoes with less support and more freedom. And don’t forget to get those hips moving too!
Hugs,
Lisa
Couldn’t agree more with your advice. I think people just overthink it. But, here’s the thing: there’s something about a well designed pump (or other) with a stiletto heel – they just work! When I see all the caricatures about people floppy over on high heels, I just don’t believe it. That has never been my experience. But then, like you, I was an ice skater. So maybe my ankles are strong and maintaining balance has been more natural?
FAM
I haven’t tried true stilettos although I would love to do it, but walking in any heels, as others here have said, the higher they are, the more difficult it would seem. What I have personally found again as some as have mentioned is that guys tend to ‘lead’ with their chest and shoulders. You know, go bull headed into any situation. That will definitely not work for wearing high heels. Learn to lead with your hips and thighs. Think about getting them right out there as you move your legs. Also, shorten your stride. That’s another thing guys do, lunge into any and everything. You also probably should try to remove the heel-toe walk that lots of people inadvertently do, which is probably why lots of heels on guy’s shoes wear out quite quickly. You know, having your foot sort of rock back to front. You have to place your entire foot down on the ground so that both heel and toe hit at pretty much the same time. I would suspect trying to balance a 100 (or more)+ frame on a little point about 1/4″ square is pretty tricky.
Besides, I’d also think that leading with your hips and thighs sort of gets those swinging in that ‘girlish’ gate most all of us sort of aspire to.
Just my suggestions from my attempts at practicing walking in higher heels. Keep at it, practice makes perfect and all that!
I had admired and fallen in love with a couple of pairs of stilettos. Finally after a year of longing and dreaming, I just had to have them and bought them. When I first put them on, I could barely stand in them, let alone walk. I loved how they made my legs look though. I was going to wear therm no matter what.
I wore them as often as I could around the house, including to bed. After a couple of weeks I could just put them on and go walking about no problem. They began feeling very comfortable and natural feeling.
I began wearing them out with my other femme attire. I just loved wearing them, the experience and ow they made my legs look was so wonderful.
Then around a month after I bought them, I wore them to a Halloween Party where I was dressed fully femme. I walked long distances, stood a lot and danced up a storm. I think it was just a case of getting used to them and breaking them into where they were comfortable.
Obviously, many of us are kind-of-fascinated with “stilettos” and high heels in general. So, as I read member’s comments, new angles emerge that I think are helpful – thus the value of a diverse forum. My latest observations relates to, strangely enough, both the angle of incline and the weight on the heel. With my size 11s, a 5 inch heels seems very natural. With a platform sole, 6 inch heels work as well, but the shoe is less flexible and it’s more like balancing on stilts. With many women’s smaller feet, a 3 inch heel probably has a similar angle of incline. Regarding the weight on the stiletto, I’ve discovered something interesting, at least for me. For several years, while I was consulting from home, we lived in a big house with a spiral staircase over a 2 story great room, 1400 square feet of engineered maple flooring, and bedrooms with deep carpeting. Although I wore stilettos for a significant part of most days, I never made marks on the wood floors and did not leave lasting marks on the carpeting. Yet, when we had company, several women, much lighten than I, with lower heels left marks on the wood floors. I did not make a concerted effort to remain light on my heels, but presumably, my natural gate-in-heels must have placed most of my weight on the soles. Interesting?
FAM
It takes a lot of practice and its still work but took me a while to get us to heavy fire boots that go half way to your knee and are not flexible but stilettos are a challenge but a lot of my dressing is a challenge at first
Takes a bit of time and practice but you’ll get there. Walking around on your forefoot/tippy toes helps, At least it did for me. I’ve been doing that since I was young
It also helps if you have high arches, which I do. I only wear 4+ inches, and my most comfortable pair are 5 inches! I suppose I lucked out with my feet 🤗
buuuuuuuut, low heels take adjusting for me. Anything lower than two I have to really think about when I walk.
The trick is in the heel strike. If you have too much angle between the ground and your foot, very strong ankles are required in order to prevent pivoting sideways with your ankle. Keep the placement shallow. That’s where the shorter stride comes into play.
Walking on your toes is not a solution as it can become very tiring very quickly.
I really love the look but just can’t get used to them. I have resigned myself to either flats or very short chunky heels. My ankles just don’t have the strength I guess. Since I am older I see that almost all gg’s my age don’t wear stilettos or very tall heels. They seem to value comfort much more than style so I am glad to blend in with my age group.
I have walked in stilettos since I was very young. I have pair of seven inch stilettos with a platform which I need to be a little slow and careful but I love them. Five inch without a platform – no problem. Six inch without a platform a little difficult, mostly because I don’t have a pair of my own to practice in.
I’ve been wearing heels since around 5 yrs old. 5 inch at that. So i have no issue with them. But i can tell you start lower and walk heel to toe taking your time and build your self up to a higher heels. when you get to a heel that you just can’t walk in or feels way to uncomfortable then the previous height is yours. Wear those and own them. The next step is putting one foot in front of the other when you walk, i.e. your hips will sway more natural without you exaggerating them.
Another trick when walking it to turn your wrist/hand out – not any further than needed where you are forcing it and it hurts, but but just enough that it feels ok. Then sort of sway your shoulder a little as you take that one step in front of the other. your entire body will take that sway and you will look more feminine.
those are you my opinions
Jennifer
On fit – yes – I have a pair of designer shoes with a six inch heel and one inch platform. I found them new at Goodwill. They fit like they were made for me. I put them on and wore them most of the day, hard floor, carpet, up and down stairs. No pain or discomfort. My go to shoes.
The answer: Don’t!
Look in a previous life I liked tennis and speed skating. I wouldn’t wear the blades on the court and I wouldn’t wear my Nike’s on the ice.
Same with stilletos. If there is a lot of walking in your outing there are better options. If you are dress shopping bring them along in a stylisth tote.GG’s know this. How many 4″ers do you see at the grocery store? On the dance floor how much to the nose bleeders on heels really move?
Unless you like emergency departments…..
Common sense works out.
So, I never had trouble in high heels from the first time I stood up(tentatively) in them.
I play ice hockey(for years) and I am used to standing on a 2mm wide metal blade for long periods of time…
So, balancing on a heel, was pretty much the same…
So, go take some ice skating lessons and strengthen those ankles girls!
Dala
I don’t really remember the first time I did wear high heels but guessing they where probably not that high.
Today – a few decades later – I have no issues with wearing really high heel stilettos, 4-6″ is what I wear most of the time. Like right now I have some 14cm/5.5″ stilettos and don’t even think about it as a problem of any kind.Most of the time the problem isn’t balance but that my wide foot have problem fit in the narrow shoe, my size is probably something like 42Wide and that’s not that common. I think it took me a long while (and many pairs) to figure out exactly what type of shoe that I can wear without it having some kind pain problem. My biggest progress is probably that I have to realise no matter how good that shoe looks I can’t wear it because it’s to small 🙁
Fortunately I almost always wear a women’s size nine. I can almost buy them without trying them on.
It really helps if you move like a woman. This is true whether in heels or flats.
So first is posture. Stomach in (which raises your center of gravity; a man’s is lower than a woman’s), chest proud. Pretend you are a puppet and someone is pulling up on your head. Shoulders back, but relaxed. Arms hanging at the side, palms facing your body.
When men move, they start with the feet and pull themselves forward. Women start with the pelvis and catch themselves as their weight shifts. Their upper body remains relatively still. This is why women appear to glide. It would be also be uncomfortable if their breasts bounced a lot with each step.
So what you need to do is to push your behind forward a bit, and when you start to move forward, move your foot forward on the heel and roll to the toe (you can do this in flats or without shoes, too) to catch yourself. If you keep your stomach in, you’ll almost be forced to walk this way anyway. This will also make you bounce a little in your behind. Keep your feet close to the center of your body. Don’t try to cross the center line like runway models do, that is just for exaggerated affect.
Let your arms hang, and let them swing naturally with your rhythm, keeping the palms to the body (a man keeps his palms to the back, and may keep his shoulders broad and swing his shoulders – think Popeye). Keep your head looking forward (or at least up),; looking down will kill your balance.
If you can get the walk down flat footed, adding the heels is not that much different; just take smaller steps and give a bigger heel to toe roll.
Steps, place the foot flat on the steps, and perhaps turn the foot at an angle. Use the handrail. I can usually go up steps normally because I only use the ball of my foot anyway. But you have to remember the heel is there when you lift it to the next step, otherwise it will hit the step and you will stumble and may trip.
I wore my first pair of heels in July 2018, a special friend loaned them to me. I’m not sure how high the heel was, but they were stiletto thin. I had watched a few youtube videos on how to walk in heels in preparation. I was quite natural walking in them. Currently I have 4 pairs of heeled shoes and 1 pair of full wedged shoes. I feel the most comfortable wearing and walking in heels under 4 inches.
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lol i call left wing!
Up to 2 3/4 inch heels no trouble walking. Any heel above that I wobble. Would love to wear 4 inch heels.
I can walk in heels but rarely walk in heels because I’m tall enough as it is. And it’s not easy to find heels in my size that are truly comfortable.
Carla
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I have read the responses with interest and noticed that very few point out the fact that regardless of being a gg or gm walking in heels is not a natural born gift. I have a teenage daughter who is “learning” to walk in heels. We have all seen gg’s who stomp and clomp like an elephant in a brush fire and never learned to exercise their feminine grace. Oddly even though my daughter doesn’t “know” about me she came to me instead of my wifey to help walk smoothly in heels. It is not some innate sense of ability but takes time and practice for anyone to walk proper and lady like in heels. How many times have we all seen women in their stocking feet carrying their heels at a dance or event, or seen women put on flats or tennis shoes to come and go from work or an event? Heels are definitely meant to be seen in and not worn for comfort, even though I love wearing them. For the record I have everything from flats to 5” stilettos and have learned to move gracefully and capably in any of them, although if I am out shopping or planning to walk a while I usually never wear anything much over 3”. So… follow all the good advice given and practice, practice, practice if you want to wear them AND look like a lady and not that elephant stomping out fires.
🍷C After several hours, walking long distances or standing a long time, my stilettos can become a bit uncomfortable. When I got my first pairs, I could barely stand in them. I just wore them lot, broke them in and got used to them. After that they became ok to wear a lot. I can’t exactly say they were comfortable. That often depends on the pair I’m wearing. They are are fun though.
I exclusively wear platform heels now, the two inch platform and six inch heel have my foot at a perfectly comfortable angle and I can wear them all night. I’ve tried non platform w/ a Four/five inch heel and they really hurt my feet!! I have several platforms in a variety of colors, I wouldn’t think of wearing anything else, oh and I’m only 5’2” in stocking feet🤷♀️
My pair of ankle strap heels were a bit of a revelation for me. I feel super stable in them. I’m not 100% sure its the ankle straps, it could be something else about the shoes that helps with stability. (They fit me better than any other heels I’ve had, that could be it too)
Even if the ankle straps don’t actually help, they look super cute!
It really is a case of practice, practice, practice.
When I started wearing heels it was a pait of spanish leather slingbacks with a 3inc slim(but not stiletto) heel and I was initially very wobbly. I soon got used to them and could even (girly) run in them. I then progressed to a pair of Mary/Janes with a 3 1/2 heel then on to a pair of stilettos with a 3 1/2 heel. The more I wor my heels the better they fitted and the easier it was to walk in them. I can now wear a 5 inch pair of courts with a stiletto heel without issues. As has been mentioned ones posture is a big thin and it is kind of easyer if ne inces rather than trying to take giant steps.
Whiost heels are not always the practicle answer, and after they have been worn for a while, the kill ones feet. This is all worth it for what they do to the calfs and derriere and how much more womanish ones movement is when wearing heels.
Love em.
Take care girls
Anne-Marie
Hi girls….two pieces of advice…..practise, practise practise…..please don’t just put them on and stagger off….as soon as you hit any sort of slope, up or down, you will struggle…secondly….baby steps and try to keep a straight back…if you lurch forward using big strides, you will slip and slide…..hope this helps girls….and me???? personally I adore heels, how much more feminine do you need???….love you all. Grace xx
I love love love my heels! I can walk in them fine but as the rest of the girls said. Practice is key. Posture is so important. When I started to walk in heels I could not seem to shake the man walk. After I videoed myself walking back and forth in the kitchen I started to pick apart what was going wrong. The arm swing or lack of is important to loose that manly gate. Also I have come to love wedges! They make your feet look so small and they are so easy to walk in. Not a substitute for stiletto’s though. Also when I started my legs would be so sore but now all day and no discomfort at all. Fit is so important. Go with a shoe that is the correct length and width for your feet. If you’re not sure go to DSW and they will be happy to help you. If you need an excuse just tell them you lost a bet with your wife. It worked for me in the early days. I don’t do that anymore. I just tell them I am a cross dresser and show them a few photos from my phone and they will jump over backwards to help you.
Best of luck girl.
Diane
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