Category Archives: Crossdressed Outfit of the Week

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

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

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.