Shoes, Shoes, and More Shoes. What Should I Wear?

Transgender women are like all women, we love shoes, and more shoes. I don’t know a single item of dress that excites more attention or excitement than a good looking pair of shoes…they are an integral part of our overall personality. The shoes you choose to wear and the way you maintain them creates an astounding impression on others.

Lots of shoesEspecially for women, shoes have to really match the dressing and the occasion they are worn on. That is why there are so many different types of women’s shoes and they come in more various shapes, colors and sizes than is imaginable.

“The look he shot her was incredulous in the extreme. “You have a filing system for your shoes?”
Norah Wilson, Guarding Suzannah

This is my wife. Every shoe is in a labeled box. If she didn’t have a distaste for spreadsheets, I’d probably have a home database cross-referenced by type and occasion.

Glamour magazine, according to stylish insiders, tells us the kind of shoes that every women needs. How do you ever make a choice? But then why. Imelda Marcos is known to have said,” I did not have three thousand pairs of shoes, I had one thousand and sixty”

Well as cross-dressers, we should be making some sensible choices keeping in view the current trends (shall I tell you how many trends there are), our dressing requirements, the occasion, and of course comfortableness. The pundits will tell you that comfort is paramount but then my favorite style icon, Clinton Kelly, said, “Sometimes comfort doesn’t matter. When a shoe is freakin’ fabulous, it may be worth a subsequent day of misery. Soak in Epsom salts and take comfort in the fact that you’re better than everyone else.”

wearing high heels

Now Ann Reinten, an Australian fashion guru with Pretastyler has done an amazing job in explaining everything we need to know about shoes as she tells us

How Shoes Can Transform Our World

shoes transform your world_opt

Justine Leconte has this very good primer on all the shoe types

Tricia Mann from will tell us the ten must have shoes for women.  I am not a fan of flip-flops (part of the ten), but I do have some really great pink sneakers from Avon. Then the folks at will tell us how to choose the right shoes for our body type and occasion. This is good to know so we can put the right one on for any event. Shoes need to be chosen carefully for that special look and fit.

And of course not all shoes are created equal, and not all are appropriate for each outfit. Pants and skirts of varying cuts and volumes look different with pointy-toed shoes than with round-toed ones, so how do you pick a pair each morning?

Have no fear, the Shoe Grid is here. Check out this handy guide from the New Professional blog to get the look you want.


And before we delve into all the types of shoes, here’s a brief primer on heel heights.

Imogen from Insideoutstyle blog has some interesting reflections on shoes. Because of foot pain, her doctor told her to wear a different pair of shoes every day. Now there’s an excuse to have a Imelda Marcus size collection. Of course, the only girl I know with a collection that size is Vikki laFontaine (happy face).

So if you are  an Imelda Marcus, then theses most beautiful shoes in the world will get your interest

Shoes can make (or break) an outfit too.  As shoes add:

They work on so many levels and are an integral part of any outfit, so having a range of shoes to choose from depending on what I’m doing (running errands versus giving a corporate presentation) means sometimes I can wear flats (actually, much of my life I’m in flats or near-flats), but other times, a heel just finishes off the outfit so much better.

I have a range of heels and I categorize them like this:

  • Car to the bar (aka sitting only)
  • 2 hours
  • 4 hours

Yes, 4 hours is mostly my limit these days for a heel (wedges are a different story if they are on the flatter side).  But of course, there are occasions when I want to wear a heel all day, for example to a wedding or special event (such as Christmas parties), where I may want to do a little dancing too along with some of the standing-around that tends to happen at such events.

Aleigha is perhaps my favorite fashionista as she knows fashion in a very earthy way. In this video, Aleigha talks about heels, heels, heels…the different types, and the tricks to find the right shoe that is comfortable on your foot (and looks great).

After watching the video, check out how to walk in high heels

And then a fun little clip  with pictures of high heels over the last century. Whether you like them or not, these iconic shoes have remained a fixture of women’s wardrobes for centuries. When wearing them, women feel taller, more powerful and elegant.

Lastly, a little on the formality of shoes

We all need a variety of shoes in our wardrobe. Shoes that work for different occasions or events. So even a shoe like a pump which is a naturally more formal shoe can vary from Refinement Level 1 down to Refinement Level 2.

formality of pumps

Elements of Pumps that Will Reduce the Formality (or Level of Refinement)

  • Pattern – multiple colors and patterns reduce formality
  • Fabric – matte fabrics, matte finish is always less formal than something with sheen or shine
  • Heel shape – the thicker and more sturdy the heel – the more it’s made for “running around” versus the slimmer and more refined the heel, the more formal (and made for sitting) it is.

Determining the Quality of  Your Shoe

Now Justine Leconte  tells us how to recognize good vs. bad quality shoes.

Finally in what we call High Heel Hacks, here are some tips for wearing those high heels all day and alleviating the pain it sometimes brings

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