Finding the perfect pair of high heels

For the crossdresser taking their first tentative steps out in the world so many questions swirl around them. Will anyone notice me? What will they think? What if I meet someone I know?Β Among all the questions perhaps the most important goes unasked: “Do these shoes go with my outfit?”

Unfortunately for many crossdressers the answer is usually no. Many crossdressers don’t spend enough time enjoying the true diversity of woman’s shoes available. Most of us are just happy if we can find a pair of high heels we can squeeze our overly large feet into. The time we do spend looking for shoes is usually results in a shoe collection that would make a stripper blush.

Now don’t get me wrong I love stilettos as much as the next girl, but it’s difficult to enjoy a day at the park in on 4″ heels. Today I’m going to share with you a few tips for finding the perfectly fitting shoe, as well as some other fun shoe styles to try. If you know all this, and just want to find some great places to buy larger woman’s shoes you can find all the details on the crossdressing high heels page.

Crossdressers – Choose Your Woman’s Shoe Size Wisely

When selecting a woman’s shoe you should pay attention to the two measures of size – length and width. The first of which is the length, indicated by numbers (8, 9, 10, etc.). If there is no width specified it normally means the shoe has a Medium width, which get proportionally larger as the shoe size increase.

En Femme Style

The second measurement is width, which you’ll find expressed by letters. AA for Narrow all the way to EE for the widest width. Β Confusingly enough you’ll also see width expressed using a different set of letters: N, M, W and WW. They’re measuring the same thing, so a handy way to think about it is:

  • Narrow: N or A/AA
  • Medium: M or B
  • Wide:W or C/D [Equivalent to a Men’s medium]
  • Extra Wide: WW or E/EE

To find your woman’s shoe size you need to add one size to your men’s dress shoe size (round up if you wear a half size), and take your men’s shoe size width and add one. So a men’s 10.5 medium would end up as a woman’s 12W.

You’ll find that shoe sizes vary by manufacturer, and it’s difficult to find the largest sizes in the store to try on. I recommend that you shop at an online store that gives you free shipping and free return shipping until you’ve figured out your size. Zappos and Endless are two great online shoe stores that do shipping both ways and have a good collection of large woman’s shoes, this page has a list with more stores selling large woman’s shoes.

Two Shoe Styles You’ll Love When Not In Stilettos

Now that you know how to find the right size shoe, I’m going to share two of my favorite shoe styles that are perfect for crossdressers. I know you all have at least one pair of pumps, so I won’t mention those again πŸ™‚

Crossdresser High Heel Ankle Boot

Crossdresser High Heel Ankle Boot

High Heel Ankle Boot

The high heel ankle boot is perfect for crossdressers. You get the sexy feel of pumps with the extra support of the boot. The boot helps keep you steady if you’re just learning to walk in high heels, and the enclosed boot makes your feel look smaller. Be careful about boots with an overly pointed toe (the ones to the left are fine). If the boots end in a long thin point your feet will look longer than they actually are, because a few inches of the shoe are taken up just for show.

High Heel Wedge Sandals

High Heel Wedge Sandals

High Heel Wedge Sandals

Another great and comfortable choice is a wedge. These high heel wedge sandals are perfect for wearing during spring and summer. The wedge is much easier to walk on than stiletto’s, while keeping you feeling sexy. Watch out for straps that are too tight. Not only will this be painful, it will make your foot look like a squashed sausage – a definite sexy fail.


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I’m passionate about creating a safe space for everyone in the transgender community to find laughter and friendship on their journey. I completed my physical transition in 2011 and through it I lost everything, and gained everything. I am blessed that I was forced to gaze inward and embark on the journey to discover and live my authentic self. My deepest wish is that all who wander here may find peace, happiness and freedom.

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Franconia Houghingtonne
4 years ago

I wear heels all the time and i get mine custom usually according to length and width from FSj. It is very difficult but maybe onlymaker is getting better?

Deborah Sullivan
Trusted Member
4 years ago

I walk naturally now in three inch heels. Have done most of my shopping at payless and have had no hassle or stares. Just have so many shoes now but we need the colors for different outfits for matching.

Tania Alejandra PiΓ±a Gonzalez

I loved so much this article, the truth is that out there are various options, and the shoes depend on the clothes style, as example, I think is a fooliness use heels if you are dressed with sport clothes.

Judy Zarro
1 year ago

I love high heels. Ive had various collections of high heels numbering in the twenties st times. Presently I find myself with 9 pairs of heels. There is nothing more feminine than putting on stockings and a garter belt and then a fine pair if heels and strutting around the house. Im used to a 5-6 inch heel usually with a platform.

Samantha Lucks
1 year ago

I’m 6ft4 but have incredibly small feet (size 7.5) in ladies shoes I’m a EU41 but in the UK that could be either a 7, 7.5 or 8! It’s best to find your EU size due to the size differences between brands such as Next/M&S/Dune

Paula Bigg
3 months ago

I love heels. High heels.My little collection has now three models, two stilettos, a scarpin and a sandal, and a block sandal.The worst part on buying them, was which would be the right size? I bought all on line, and the sellers had a sizing chart showing the foot length for which size. For the first and the last, was just find my foot length. For the sandal, was similar. But after I bought, the seller said that the size I choose was out of stock and, as really want that sandal, I had to accept a bigger.Anyway, I do… Read more Β»

Active Member
3 months ago

You’ll find that shoe sizes vary by manufacturer Keep in mind that standard shoe sizes (…6, 7, 8…) are arbitrary even for one company’s own products. I have had shoes in sizes 10-14 fit properly. I even have one pair of shoes from a fairly reliable company that has a slightly bigger size for one foot than the other! Some manufacturers use millimeter sizes which should be less arbitrary because they refer to an actual measurement, but I haven’t been able to test the accuracy much because few manufacturers have yet to supply these measurements. Some on-line stores do, though.… Read more Β»

Trisha Rave
Active Member
1 month ago

Thank you for advice;

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