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Alternative title: My history of footwear
Back in early 2023 my crossdressing started to take off, so I decided I needed a pair of ladies shoes if I was going to head outside.
I started with a pair of simple black lace-ups - flat base but with the heel thicker than the sole so it had a very slight slope. Easy to walk in, sort of feminine, but not overly stylish. However, it was a useful start.
Come the month of May and it was getting warmer, so I needed lighter footwear. I went to the opposite extreme - strappy flat black sandals! I love them. They were very easy to wear and I think they looked great.
Then I spotted a pair of flat black Mary Jane shoes which were great for less warm days. Fell in love with them as well. Again, very easy to wear.
Moving into autumn I decided it was time to start getting more ambitious, so opted for a pair of patent navy 55mm heels. Ouch!!! I soon discovered the meaning of pain. Blisters and corns. OK, I have now dealt with the blisters and am combatting the corns, but it seems to be a never ending battle. The most recent development is a big toe nail developing a delicate shade of purple - which would have been a good match for a dress I wanted to buy but which did not fit well (my wife bought the skirt in the same material, but that is another story). So, back to the question - WHEN DOES THE PAIN END?? But don’t get me wrong, I really love the heels, and my wife thinks they look great, but it is a challenge wearing them. And I know many of you are thinking “only 55mm, c’mon you wimp”, but I do plead extenuating circumstances. A little accident** in the year before my retirement left me with 2 slightly different size and shape feet.
But moving on to today - this morning I saw, coveted and bought a pair of black ankle boots in a lovely soft leather with 60mm heels. They are extremely comfortable and will be great through the winter. And they are far more stylish than the original lace-ups I bought.
Well, that’s my story so far, but I would love to hear how others have conquered the challenge of wearing heels.
Hugs
Rebecca xxx
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**PS A crossdressing-free epilogue: “The Accident”.
I managed to break both heels simultaneously. One just a hairline fracture which healed easily. The other … well the heel bone shattered, went everywhere, and is now held together with a lump of metal. When I was eventually able to walk again (with crutches!) I had to fly to Germany on business. I was all ready with X-ray pictures of my foot because I expected the metal in my foot to trigger the Heathrow security scanners. But NOTHING HAPPENED! So much for security scanners! Then when it came to boarding the aircraft British Airways (unexpectedly but thoughtfully) approached me and invited me board first. I was travelling with a rather younger but very attractive colleague who immediately jumped up and said (in an effort to cash in on my good fortune) “I’m with him”. At that point I briefly entertained the thought of mischievously saying, rather loudly, “Yes, is that OK, she’s my mistress”, but chickened out. Anyway, that was a few years ago and the foot healed well. I haven’t needed the crutches for several years, but my feet still differ slightly in size and shape.
And finally - apologies for the epilogue, hope you didn’t mind me adding it.
I also have different size feet from a foot accident that makes it hard to get a good fit in shoes without buying two pairs in different sizes and that doesn't work that well since the size difference is a half size and larger shoes don't come in half sizes. So, I mostly buy open toe shoes and shoes with straps to help hold them on. I love heels though but don't get many opportunities to feel the pain.
Hi Michelle, I decided to not even consider buying shoes of different sizes - the cost implications put me off that idea. Like you I have found that shoes with laces, straps etc to hold them on work well for me, but I still love my pair of heels and will work on re-conditioning my feet (and the heels) to be compatible with each other.
Rebecca xxx
@fembecky I read the title of this post and thought .... OH NO!!!! WHAT'S HAPPENED?
TALK TO ME REBECCA!!!!! I'M HERE FOR YOU.
I leapt to the keyboard and steeled myself for an evening of help and support.
Then I read the actual post. I realised that you were talking about shoes rather than experiencing an existential crisis.
You're a very bad girl.
Ellie x
PS - love my strappy sandals, and my wedges. Christmas treats to myself (finances permitting) will be some stretchy knee-length boots and a cute little pair of ankle boots.
Hi Ellie, To quote my Forum mentor (who taught me all I know about it): The title itself needs to be given a bit of thought, otherwise people will scroll past it and it can quickly get buried! So I took that advice to heart ...
Thanks for all your help Ellie 
Rebecca xxx
@fembecky I would recommend you to take a look at Zalando and search for a shoe brand named Anna Field, they come in bigger sizes with different fits like narrow and wide and they are also sized in half sizes and best of all reasonable prizing and at least in Denmark free freight. I buy most of my shoes from that company and are happy with them. If you need to buy bigger sizes than you need for your smallest foot then just add an extra sole in the shoe which is to big for you.
I’ve been fortunate in never suffering any pain, blisters, etc from wearing heels. Perhaps all the years of wearing Western boots prepared my feet for heels.
@fembecky OK my lovely.
About those black ankle boots that you saw, coveted and bought.
a) where did you see, covet and buy them from ... and was it online? Spill the beans.
b) I'm a 9 (but really 9.5) in men's UK sizing. Am I safe buying women's shoes in the same size, or do I have to shift up a gear? (in the US I'd have to add 1.5 but I don't think that's the case here).
The reason I'm asking all this is that it's payday today!
It's been a rotten week at work. I'm surfing the net for shoes in search of an endorphin hit.
Current targets: ankle boots, and a pair of knee length boots. Both probably in black. Don't want toes pinched, open to something a bit stretchy around the lower leg. Heels, but not TOOOO heely.
Classy, stylish ... the complete opposite of me.
Let's open to floor to other UK readers too. You know I'm hopeless. Feel free to pitch in.
Hugs
Ellie x
Hey Ellie, I feel for you. Our daughter in law was a teacher and recalled rotten days and events. It's a vocation which ought to be satisfying and rewarding, but the pressures these days undermines much of that.
Now for the big reveal. All my footwear and almost all my clothing outerwear have come from Hobbs. I realise it is far from the cheapest source, but I have accompanied my wife on her visits to Hobbs (especially the Cheltenham store) for several years and have built up a good rapport with the staff there who have given me invaluable guidance and support.
The boots are the Rosella Trim Ankle Boots in black. I had seen them in the store for a couple of weeks and had picked them up, felt the softness of the leather, toyed with the idea of buying them but had to convince myself it was worth spending that money. Then they had a Black Friday 20% off everything sale, which gave me the incentive to move to the next stage ... so I asked to try them on and immediately fell in complete love with them. Like all Hobbs items, they are available on-line and are easily returned either in shops or by post. For this time of year they are my ABSOLUTE FAVOURITE footwear and each morning I select outfits that they will go with - just so that I can wear them!
Now, how do we compare men's and ladies sizes? I can only really go by my own (somewhat idiosyncratic) experience. I was a 7 or 7 1/2 in mens size. I had to go up to size 8 or 8 1/2 in mens when I messed up my foot and had to replace all my pairs of shoes (fortunately not too many). It took about 4 or 5 years following the accident for my foot to reduce back to near normal size, but it does occasionally have a hissy fit and swells up for a few days or weeks, so I have continued to keep with the larger size. As far as ladies shoes are concerned, I started with Continental 42 (equiv to UK ladies 9) but the 2 recent purchases are both 41 (ladies 8). My impression is that UK mens and ladies 8 is about the same in length, but there is a difference as a result of the stying: ladies shoes tend to have narrower toes and I also get the impression there is less vertical space in the toe area. In the end I guess we just have to build up our experience by trial and error.
And as far as being classy is concerned, I bet given the right boots and outfit you will be very classy! I look forward to seeing the pictures when the time is right for you. Meanwhile happy shopping.
Rebecca xxx
Hiya. As Rebecca says, UK sizes are pretty similar in length but narrower.
I’m size 8 (or 8 1/2 in walking boots or running shoes).
I’ve found most success with ladies wide fit.
Size varies between stores, and even shoe types though as I’m sure you know.
For instance, my favourite heels (on my profile pic) are 7.5 wide from M&S. I’ve got some Mary Jane heels from Next that are size 8 regular fit as Next don’t do many half sizes.
My ankle boots are also from Next, but are size 7 wide fit.
For boots, my wife always wears a pair of socks over her tights for comfort.
I wear some trainer liners over my tights with my ankle boots. I found that they tend to rub against my ankle bones if I don’t.
I love my heels. I can wear them all day. I can help but be happy in a pair of heels.
That said buying the right pair makes a huge difference. I have a fee pair of size 9 that crush my feet and make them hurt. I need to stretch them a bit. I have other 9s that almost fall off and can be worn like bedroom slippers.
I have 10s that fit and 10s that gall off.
The right fit is a matter of trying many different styles and brands. I am a cyclist and a runner so strong feet, ankles and calves.
So work on finding the right pair
Paula
Hey Paula, You are right, I need to try more styles and brands to find the right ones for me. Having said that, here in the UK many women wear trainers or similar footwear, so the selection of heels is more limited than it used to be. Nevertheless I will keep looking. Thanks for the response.
Rebecca xxx
@fembecky Pink trainers can be quite a good look with the right outfit 🙂
Hugs
Ellie x
(I briefly pondered why no-one has ever produced trainers with heels. Then I imagined what they might look like, and realised that I'd answered my own question).
Oh Ellie trainers with heels, a secretary at my hospital wear some trainers with heel ok wedges but anyway they look awful. I would rather walk barefoot than wear these very ugly shoes
@clarissa2 You mean that such crimes against nature actually exist???
What fresh hell is this?
Speaking of hell, how do you feel about Crocs?
Ellie x
Just had a look at a Croc web site ... not for me, not in a million years. Even if they claim to be very comfortable! 
Rebecca xxx
@fembecky You have chosen wisely.
If you'd said otherwise we would no longer be friends.
CROCS 
Hi Rebecca, Here's a few things that I've learned through the years from professional dancers and maybe they will help in some way. I'm 5'5" and 122 lbs. with one foot a little bit bigger than the other along with a hammer toe and 3 other broken toes that have healed over the years. I wear heels up to 4'' but usually average 3'' stilettos for a night of dancing (and I do dance all night). So, first of all my shoes are usually leather (they fit, stretch, last long and mold to my feet. Never wear ill fitting shoes or you risk more foot problems. Next I almost always put pads in the shoes (which are already a very perfect fit or I won't buy them). The pads can be tape style that stay in by themselves or with carpet tape, glued in with silicone or just placed in. I will also cut pads out of old mousepads or stuff toes with wads of upholstery foam as needed. I also have shoe stretchers and can add little wooden bumps to them if I want to make some room for an errant toe but that's getting technical. Definitely trim and file your toenails carefully so they don't bruise or tear off. Next I really try to avoid any injuries ahead of time so if things are hurting I will switch to ballet flats or socks if necessary until I can get it to stop. I also limit my time in my dance shoes to the dance floor and wear flats or sneakers to and from the ballroom to save my feet and shoes (you can just pop shoes in a big bag and toss it under the table) I don't recommend this but I have friends that lived in their heels for their job and in between work breaks would stick their feet in the toilet and flush until they cooled down and didn't hurt (and then put the heels back on and went back on the floor). So cooling down feet (use ice, not toilets) will help. Also, treat things like corns and blisters regularly or see someone and have it done. Wear a soft bandage over any injury. Lastly, wear your heels on a regular basis so your feet and legs are used to them. If you have a big event like Keystone coming up then I suggest that you wear your heels 1 hour a day each day for at least a week before going. That way you will be used to the shoe and can take any corrective measures needed before that last moment. I hope this helps. Marg
Thanks Marg, that's a lot of useful information. I think I'll skip the toilet treatment though.
I think one of my mistakes was to start with patent leather (which I LOVE the look of) rather than a softer leather. I'll have a go at stretching my shoes, and I will focus on getting my feet back in shape and keeping them in good condition. But I will wear the heels whenever appropriate, but not for dancing in my case (the phrase "two left feet" comes to mind).
Rebecca xxx
Wow Marg, a ton of great information on how to avoid foot problems. As a shoe and heel addict that doesn't get to wear ladies shoes often I got a lot of great tips here.
@michellemybell Glad they helped Michelle. I learned a lot hanging around with dancers. I always thought that the Lido De Paris and Jubilee dancers were like the NFL players of the stage. Hugs, Marg
For me I just see it as a part of being a woman. I love my heels and see them as a part of my own style that I'm just not willing to give up. Having said that, I'm careful as to the shoes I wear and won't wear shoes that look amazing but hurt my feet. I just look for shoes that are comfortable and fit my style. Lots of trial and error for sure! One thing I have found important is to make sure my feet don't slide down into the footbed. When this happens, I get blisters on the tops of my toes which are painful. To avoid this, I use non-slip, footbed pads. I have also heard about spraying the inside of shoes with hairspray to make them a little sticky. I haven't tried this yet but I makes sense to me.
Hi Lauren, I get blisters on the tops of my toes which are painful. Yes - that's part of my problem. Also on the outer edges of the little toes. But I haven't heard of non-slip footbed pads. I'll try searching for them. Thanks for the tips.
Rebecca xxx
I can only wear block heels, not stilettos. Anything above 2" tall is too uncomfortable. Most of my shoes are open toe and all have to have a strap to hold my foot in place.
@d44 My new ankle boots have a block heel which is really nice and stable. My patent heels have a heel that is wide side-to-side but short front to back (I don't know if there is a special term for that style). Anyway, I chose them because I started to realise that one of my feet strikes the ground in a different way to the other, and with stilettos I would have a real danger of turning my ankle over sideways. I have also noticed that when I walk with heels through the local shopping mall the sound of one of my feet striking the floor is different from the sound of the other!!
This is all a real pain because another pair of shoes I have seen and fancy do have slim heels. Oh well ...
Rebecca xxx
