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? 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.

EnFemme 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.  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 🙂

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.

EnFemme

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Leslee
Leslee
13 years ago

I made the mistake of buying sandals without a strap for the heel. They would not stay on at all. I love the look of sandals and had to buy two different pair but this time with a heel strap. I've also found out standing on heels is uncomfortable so I started looking for cute flats or wedges.I know heels are so sexy but after awhile logic and lack of pain prevail.Notice how young girls wear the high heels but as they get a little older the height drops on the heels.Yes high heels are a must but wear some… Read more »

guest
guest
13 years ago

The ankle boots are so sexy with tight jeans! I love that look!

rogina garter
rogina garter
13 years ago

Aerosoles,Clark,Bass,,Soffti,Bjorn,are all comfortable,quality brands with a lot of choices for T girls.I avoid pumps,slingbacks,stilleto heels,etc,as they don't go the distance,comfortably.Cork wedge sole sandles are a good summer choice as they are easy to walk the distance in…After,living for a year in Chicago,I know what "walking distance" really means!!

Elizabeth
Elizabeth
13 years ago

I have found that for everyday wear (and walking, etc.) if I limit the heel height, regardless of the sctual footprint of the heel, I am much more comfortable. I have looked at many women's feet in the office, and outdoors during lunch hour, and nearly all of them are wearing something in the 2" range. Bass and Rhommerson seem to be made on a slightly wider last, and fit me comfortably. In those brands, I can be comfortable in a 2 3/4" or 3" heel.

Georgette
Georgette
13 years ago

Go to sexyshoes.com for great deals. Georgette.

Phreida' class='avatar avatar-64 photo' height='64' width='64' />
Phreida
7 years ago

I would like to add Lane Bryant and Torrid to the list of shoe stores . The selection is limited at times but , the size and fit work out good . I have good luck with both . Payless seems to be backing off the extended sizes in stores if you are into mail order they are fine . I wear wedge platforms most of the time as age is starting to catch me . Looks like “Hush Puppies" may be close . LOL ! My sisters have introduced me to Keds Classics and they go well with a… Read more »

becca' class='avatar avatar-64 photo' height='64' width='64' />
becca
7 years ago

I have one pair of very pretty spike heels. I love standing in them. They look and feel fabulous. I love how tall I become in them. The sight of my calves in them is so beautiful it arouses me. One disappointment is that I am unable to walk in them without holding on to furniture. 🙁

becca' class='avatar avatar-64 photo' height='64' width='64' />
becca
7 years ago

I love the look of boots for ladies, and trans ladies. The combination of tights and boots really excites me. 🙂

Kim Cummings
Member
Kim Cummings
7 years ago

Most of all, I love my patent leather high heels. I enjoy the way they enhance the look of my legs, making them look longer and more importantly the sensuous feminine look of them. I wear a size 12 and found a good source of larger high heels. Fetishes I guess play a role in this, but I think it is not applicable for men as women can have all the shoes they want. I am tall so I can not pass as a woman. My wife is very good about the fact that I enjoy wearing my own pretty… Read more »

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