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.

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.

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Dedicated to creating a safe, supportive and welcoming environment for everyone in the transgender community.

Latest posts by Vanessa Law (see all)

  1. Wanda Silver 1 day ago

    I definitely agree that you need a pair of stilettos for some outfits but for just everyday outfits and comfort a nice pair of 4” Mary Janes look great and are very comfortable for all day wear. I also enjoy open toe shoes as I can show off my cute polish. It is a very sexy feel.

  2. Marie Sweets 2 weeks ago

    Hi Girls, I certainly feel all feminine now, I just went to the department store and bought 2 pairs of women’s shoes, (size 10 Ballet Flats). Now dressed in a black Minimizer bra with breast forms, black panties a black full slip, black pantyhose and new black ballet flats. ,Start at the ground level and work up, heel wise.

  3. Charlie Jade 2 months ago

    I wear a size 12 womens shoes and that’s as far as some stores sell. I’ve bought a few pair at Ross, and Nordstrom Rack.

  4. Hippie 5 months ago

    I can’t find shoes that don’t have a heels. Flats to tennis shoes.

    My regular men size is 15 1/2. So going by the rules you listed here. I should shop for a size 17 in womens.

    I’m also well over 6 feet tall. I found heels but at my height I already stand out like a busted dumb.

    Do you have any advice for people over 6 feet tall with large feet?

  5. Tahlyia Cuvier 1 year ago

    I do have trouble finding the right shoe size. Thank you for narrow it down for me, at what size I should get.

  6. melyssadawn 1 year ago

    The adage of adding one size up to your shoe measurement and one size to the width as described above really only works in the U.S.. UK sizes are approximately the same wether male or female IMO. I take a Mans 9 , but if I wear a ladies size 10 as the formula suggests , then they are massive and in no way fit. If I wear a woman’s 9 they fit nicely , though finding them in the shops is really hard which is why I usually have 8’s , okay they pinch but but at least I can buy them easier lol

  7. Kim Cummings 1 year ago

    Yes, our special desires for our own little world of difference in the area of high heels and other things that are part of the reason why we are into our individual needs to be able to finish the look we seek.

  8. Kim Cummings 1 year 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 feminine outfits and high heels. She is very good at applying makeup. We often go shopping for our intimate apparel and high heels together. The Internet makes it easy to get the most lovely and sensuously beautiful and pretty thing’s. I will always wear my favorite attire and especially the high heels and pantyhose together with lingerie.

  9. becca 1 year ago

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

  10. becca 1 year 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. 🙁

  11. Phreida 2 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 lot of outfits (even Men’s ) for summer … just my opinion .

  12. Georgette 7 years ago

    Go to for great deals. Georgette.

  13. Elizabeth 8 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.

    • Vanessa Law 8 years ago

      I'm with you Elizabeth – for everyday wear 1-2" is more than sufficient, and comfortable too. I save the 3" heels for a night out 🙂

  14. rogina garter 8 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!!

  15. Vanessa Law 8 years ago

    Glad to hear it hon! One of my favorites 🙂

  16. guest 8 years ago

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

  17. Leslee 8 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 cute colored polish so when you have to take them off you can still feel and look sexy. Cute shoes without discomfort are there but be picky like any girl would be. Its very easy to become a shoeaholic, I'm one of them..

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