Why crossdress? Questions to ponder

Finding Crossdresser Shoes: Your Guide to the Perfect Fit

As a new crossdresser, one of the biggest challenges as I eased into crossdressing was finding crossdresser shoes that fit. Add to this the adventure of trying women’s shoes in a store (not!!!) How can one avoid having a disaster with that first pair of shoes? Keep reading, and I will explain how.

Finding Crossdresser Shoes: What Size of Shoes?

Size does matter for the new crossdresserLet’s assume that, as a new crossdresser, being seen in the women’s shoe department is not something you want. What can you do to discover your women’s shoe size?

If you are in the United States, assume that the size of a woman’s shoe is 2 sizes larger than your men’s size. You will also need a wider shoe. In my case, I normally wear men’s size 11 D, a medium width. My normal women’s size is 13 W, which is two sizes larger and one size wider.

By normal, I mean that women’s shoe sizes vary from manufacturer to manufacturer, just as they do for men’s sizes. With men’s sizes, I am usually 11 D, but sometimes a particular shoe requires a larger or smaller size. The same holds true with women’s sizes.

If you don’t feel like guessing, you can also go to a shoe department that has one of those shoe sizer devices. You can have a professional size your foot, then check to see what the corresponding women’s size is. Personally, I opted to do the math because, as a new crossdresser, I couldn’t handle the potential embarrassment.

Finding the perfect size of shoes

Finding Crossdresser Shoes: The First Pair

To be realistic, finding a perfect pair of women’s shoes probably won’t happen the first time. Mine was way too small and tall. That’s why you want a strategy that will walk you into success.

Rather than focusing first upon style, focus on getting a comfortable, well-fitting shoe. Without a well-fitting shoe, a pretty style won’t do much for you if you can’t put it on your foot. Once you understand your size, you can spend the big money for the perfect looking pair.

eBay: Great Choice for First Crossdressing Shoes

This article has affiliate marketing links. Advertising supports the work of The Crossdresser Report, which earns a small fee when you buy something. There is no extra cost to you! Thank you for your support of The Crossdresser Report!

I have found that eBay is a good source of fairly inexpensive shoes. The best thing is that one can filter the shoes by size. When I am experimenting, I like to sort the results by price so that my bank account isn’t emptied as fast.

Start your eBay search by going to the women’s shoe page. After narrowing the choices by type (heels, for example), you can see choices for filters on the left column. Click the nearby See All link, and you will be able to choose any size and width.

As you begin to narrow your choices, be sure to check each seller’s return policy. Of course, some sellers do not allow returns. Because I don’t know whether the shoes will fit, I avoid these sellers.

Of those who allow returns, you will usually be refunded only the price of the shoe. The seller will not normally refund the original shipping cost, and you will have to pay for return shipping. This may seem unfair, but I think it is okay because this is, after all, a trial pair of shoes. I view it as the price I gladly pay for not being embarrassed in the shoe store.

Finding Crossdresser Shoes: Trying Your New Shoes!Finding Crossdresser Shoes: Trying Your New Shoes!

In all of my experiences as a new crossdresser, I thought one of the most exciting was the delivery of my first pair of shoes to my doorstep! I was 100% positive all of my neighbors watched the postal worker drop the shoes at the door, but I didn’t care! My shoes were here!

As you already know, they were in fact too small. They weren’t long enough, and I would have to crack my foot in half lengthwise to get them to fit the too-narrow width. Believe me, I tried everything to get my feet to fit. Alas, I felt like Cinderella’s step sisters trying to fit my feet into the glass slippers.

Being Careful When Trying Your New Shoes

Carefully open the package. If you need to return the shoes, you will need all the original packing materials. If there are tags attached to the shoes, do not remove them. Return the shoes in exactly the same packaging and condition as they arrived.

If you are planning to return the shoes because they don’t fit, remember this rule above all others: Do not scuff the shoes, including the heel and sole. This means that you must try wearing them on a carpeted surface only! Do not walk upon a hard or dirty surface until you are 100% sure you are going to keep these shoes.

Most stores need you to contact them before shipping the shoes back to them. Be sure to do this before you repackage anything because they may have special instructions for you.

How is the Fit?

When deciding whether the new shoes fit, here is what to consider. The first need is that the shoes are comfortable. If the shoes are squeezing your feet, you are in for some major discomfort. Although shoes do break in, they won’t change much. I know, I have tried! The best bet is to have shoes that feel comfortable right out of the box. That makes all the difference in the world.

On the other hand, you don’t want loose shoes. When this happens, the shoe will rub against your foot while you are walking. This will lead to a blister in no time. Look for a snug shoe, not a crushing shoe.

The perfect shoe!

The Perfect Pair!

If you don’t have to return the shoes, congratulations! You have successfully found your women’s shoe size, and they fit perfectly. There’s no need to return them, and now you can enjoy the feeling of strutting in your own feminine shoes. Enjoy with some new earrings!

If they didn’t fit, don’t give up! It took me four tries before finding crossdresser shoes that fit properly. Rest assured, the experience is wonderful once you do find the perfect fit. Keep at it, because that perfect pair may arrive in the next box at your doorstep!

xoxoxo Sami

p.s., Here are other articles related to shoes. Enjoy!

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Posted by Sami

Sami has been a part-time crossdresser for about 5 years. Although she still has a lot to learn herself, she is enjoying teaching new crossdressers tips that will hopefully help them on their adventure.
Besides enjoying her time with her family and working as a web developer, Sami loves to travel, make home improvements, and create jewelry in her spare time.
Read more about Sami by clicking her name.

5 thoughts on “Finding Crossdresser Shoes: Your Guide to the Perfect Fit”

  1. Useful article – thanks for posting. I’ve never found any particular problems in sizing – I just get a UK women’s shoe in my size (which is the same as my man’s size). The biggest issue is that there aren’t so many styles available for our larger feet. Well online shopping has made things a lot easier – especially for shoe shopping. I am a lifelong crossdresser but for years I was way too scared to buy some women’s shoes from a physical store. Thank goodness online shopping came along and made the whole process a lot easier!

  2. I enjoy wearing women’s shoes at night and taking walks in a local park between 12 & 3 AM. It’s the only time I feel I can prance in them and really understand heel walking. Finding heeled slip ons that fit is extremely difficult. So I’ve normally got to find a lower shoe size or narrower fit. My women’s shoe size is ironically smaller than the equivalent male size and women’s undersized sandals are easier to fit than oversized heels leaving aside oversized heels. As there’s no real consistency I can fit shoes of EU sizes 41 (sandals) to 45 (trainers) to get the right fit. Here’s another 2 cents: https://hubpages.com/style/Shoe-sizing-in-a-crossdressing-context

  3. Nice webpage. As for “the shoes,” I have been wearing gals heels in public since 1995 and love every minute of it. It was nerve wracking at first but with time I realized that really no one cares. Yes I have gotten some looks and stares, but never a negative comment and several very positive comments. I don’t wear heels to “show off” anyway, I just like the look and feel, and wearing heels makes me happy. It’s hard to explain. I am lucky that I have a supportive wife as well. Have fun and enjoy the shoes!! sf

  4. I must be blessed as I love wearing 4″ stiletto heeled court shoes & luckily, I have no problem as my feet are a Uk women’s size 9, & to surprise even thigh boots fit me in a 9 & yes online shopping is fab as it all comes discreetly packaged whether it’s a dress or shoes

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