Wednesday, May 14, 2025

Shoes for a Desert Island Getaway (or Motel Escape)

By Brenda

In conversation with a new sister (Jennifer), who is very eager to go from first steps to a lot of JJ steps very quickly, I was asked what shoes should one buy and how do you go out and buy them as a male?

First, I was curious as to when she wore heels for the first time and she replied it was not that long ago and was there anything that she preferred. She indicated that several of her coworkers wore black pumps with a mid-heel and I like to be dressed as a secretary. I wore my mother’s friend’s high heeled stilettos every time they came over to gossip, but my mother never really wore pumps (she preferred sandals). I was surprised that shoes did not play a big role in Jennifer’s life before now.

Femulators are like regular people except that they also enjoy to wear woman’s shoes especially when they are out and about. High heels can also be considered a fetish object, but to us women, it’s something a smart girl loves to wear. Femininity can be defined by the right choice of shoe and can express your fashion sense very quickly. Once your foot has entered into the shoe, the brain already starts shifting quickly into feminine mode.

Along with the confidence boost that comes with more height, you might feel more positive about the way you look physically when wearing heels. High heels slightly alter the proportions of the body, lengthening the silhouette, accentuating calf muscles and making a person appear slimmer. Try different heel sizes and watch yourself in the mirror as your body reacts to the heel height. Shoes are very personal and I observe with a sharp eye what others are wearing or what style they enjoy the most. 

Shoes can quickly be an obsession and soon one is searching for storage solutions to accommodate them all.

I shopped at Payless as they offered low prices, had many styles in my size available (they stocked 10, 11, 12 and sometimes 13) and at times, I would be able to quickly try them on due to the store layout. They were everywhere and an affordable way to shop. You could be a real diva and buy Christian Siriano as the designer brand. I adore a pair of flower print pumps that are not just super comfortable, but look fantastic with a blue dress that I found in a thrift shop. In fact, in Stana’s sidebar photos, I spotted several pairs of Payless shoes that we both own 

I will say that I prefer quality brand names as they are more comfortable, made of leather and usually are stylish. There are lots of cheap overseas brands and some are better than others when it comes to quality. If you ask an airline flight attendant, she may mention Clarks, Naturalizer and Dream Pairs (Amazon) as go-to brands. 

It’s very easy to just ask, “My wife spends a lot of time on her feet and she is very fashionable like you and has an elegant style her friends say. I am sure she would adore a pair of shoes like yours and may I ask where you got them?” Seems to work very well. 

One time the attendant told me they were not for sale and I repeated my story. She apologized explaining that she gets asked a lot about selling her shoes and honestly if she asked for $200, they will still buy her shoes” 

I laughed and replied, “Honestly, I would give you $200 for the flight attendant outfit instead and let my wife buy her own shoes. (I need to ask Norah and Paula G about their flight attendant look). 

The low-heel Mary Jane is ideal for the aisle and the classic pump is your pair for walks across jet bridges and airport terminals on the way to the shuttle bus. Maybe, a quick stop to swap out for Mary Janes when the calfs start burning and the toe-pinching is unbearable (a good sign your shoes aren’t fitting right).

How to Shop

Online, use the size guide and feedback comments (shoe fits true to size or very narrow) to double-check, saving the headache of returns. 

In store en homme, find a pair in your size, check to make sure they are W (Wide), pay and try them on in your car and if they don’t fit right, return those 30 minutes later after a coffee break.

You can show a picture to the saleswoman and calmly say, “I have been told to buy these for my daughter’s birthday. Can you help?” If she replies something about domination or sissy role play, just explain that your daughter’s birthday is coming up and my wife says she would love these shoes for a wedding event and can I pick them up for her.

“I am crossdresser, not a transvestite and I will try these on when you are not looking”

The other trick is to have a pair of men’s pants and shirt to try on and in the cart is a dress and shoes. When you go into the change room, bring all four items, but check if you have a half door exposing your feet to others. 

I was en femme and popped into a thrift shop about 30 minutes before closing and it was not busy at all. I tried on four pairs of heels, two dresses and a business suit. I realized afterwards that the bottom third of the door was open to view, but it appears no one noticed. I stuffed a bag for $10 and couldn’t wait to get back to the hotel to try everything on. I even found a handful pantyhose to put in the bag. 

In-Store en femme, no problem. Enjoy your two hours of shoe shopping and fitting and don’t forget to keep the free nylon socks. Feel free to ask the sales help for suggestions.

For Sale Ads: If you wish to make friends with others that are in purge mode then go to it but be careful about your privacy and security. Apparently, women are finding creeps with a shoe fetish and even a foot fetish buying on Craigslist or Kijiji. I saw one ad saying “Male Crossdresser with too many shoes for sale SZ 12 and 13 and come try them out and have a chat”. It would be funny to go and find out it’s your Boss trying to raise a few bucks for Louboutins.

Thrift shops do a brisk business in shoes and with careful observation and some luck you will be rewarded with stylish fashion brands at low cost. I have noticed larger size shoes are priced higher than a size 9 for example. They know that its men who buy these shoes and Kate Winslet (Size 11), Beth Stern (Size 12). I have found Nine West, Michael Kors, Jessica Simpson and other designer shoes over time in my size. If the shoe doesn’t fit, return or donate it back to the charity group.

Packing for a desert island getaway sounds like a fun adventure! Here are some stylish high heel options that will keep you looking fabulous.

Classic Black Pumps

Classic black pumps are a timeless choice that adds a polished look to any outfit. They are versatile and can be worn with various styles, making them a wardrobe staple. Opt for a closed-toe, full-back style with a heel high enough to help loosen up your hips as you walk

A timeless choice that adds elegance to any outfit. Perfect for evening wear or formal occasions but is also a secretary worker staple. The key word is a style that has endured for years. The normal height is 3 inches with lower kitten heels an option. The stiletto skyscrapers are for indoor play due to their lower walkability rating.

Nine West has offered classic heels ideal for the office girl and for the party girl for after work drinks. The Jessica Simpson brand goes up to size 12, Choose a sexy pointy toe or a rounder more comfortable one for comfort. Click here for one that has a heel ideal for spending hours at the mall.

Nude Heels

Versatile and flattering, nude heels can be paired with almost any outfit. They also make your legs look longer. Heels affect not just your posture, but also the overall “look.” Chunky heels make walking so much more comfortable. Click here for an example.

D'Orsay Pumps

D'Orsay pumps are elegant and chic with the sides cut away to reveal the arch of the foot. This style is perfect for showing off shapely legs and adds a touch of sophistication to any outfit. They are a great choice for enhancing your feminine image. Click here for an example.

Wedges and Platforms

Ideal for mastering walking in heels, wedges provide more stability and comfort while still looking stylish. These work well with higher heights especialLy with the platform.  Click here for an example.

Tall Boots

Knee-high boots are sexy and sassy, perfect for adding a bold statement to your outfits. It pairs well with a short (check for stamp of approval) or long skirt and ideal for jeans. Click here for an example.

Ballet Flats

Ballet flats are perfect for those who prefer comfort without sacrificing femininity. They are especially great if you're taller or want a stylish look without the discomfort of high heels. Ballet flats come in various designs and colors making them a versatile addition to your shoe collection

Every girl keeps a pair in their handbag as high heels can sometimes get tiresome. Every woman goes thought this in life and the only cure is to take a break and wear flats. There are even pocket foldable flats that are more after party cab shoes than daily wear. 

Ask an airline stewardess for the comfy brands as they enjoy comfort and style and they may give you this link.

These styles will ensure you have both comfort and fashion covered during your desert island getaway. Which pairs are you most excited to pack?

If you can only have one pair maybe, the Mary Jane offers comfort, height and curb appeal.

I would add these (click here) for a week of fantasia instead of the boots because slingbacks are pretty hot right now in a lower heel and every girl needs an animal print at one point in their life.

High heels make me look taller and more proportioned. I also wear skirts or dresses and they usually look better with heels. I have great legs that look their best in heels. I feel confident walking in them and definitely have more of a presence. I just feel so feminine and myself in heels.

Also high heels are just gorgeous on their own. I have dozens of pairs and love picking the ones to go with my outfit. Mary Janes? T-straps? D'Orsay pumps? Oxford heels? Oh, my gosh, they're all so good. If I could only bring one pair that covers comfort, walkability, style and sexiness then it would be this shoe (click here) and it’s no wonder it’s sold out. 

Shoes, shoes, shoes, so many choices and so much fun!

Sidebar

Pumps are a classic and elegant shoe that can elevate any outfit. It is the staple of every femulators wardrobe. Here are a few tips for choosing the perfect pair:

Heel Height: Choose a heel height that you feel comfortable walking in. If you're new to wearing heels, start with a lower heel and gradually work your way up.

Fit: Make sure the pumps fit well. They should be snug, but not too tight and there should be no pinching or rubbing. Try on shoes later in the day as feet swell. Use online size guides to double-check fit.

Material: Opt for high-quality materials like leather or suede for durability and comfort.

Style: Consider the occasion and your outfit. Classic black pumps are versatile, but you can also experiment with different colors and designs.

Take advantage of BOGO sales: many retailers offer deals all the time as shoe styles change every season.



Image Source: Elágia
Wearing Elágia


Mark-Paul Gosselaar femulating on television’s Saved by the Bell.

13 comments:

  1. AnonymousMay 14, 2025

    Hi Brenda!
    When I was asked about being a flight attendant, I had a pair of black knee high Cole Haan boots on, and have noted some flight attendants wear high boots in colder months. I usually note them in a lower wide heel, and often a Mary Jane as these options give a firm footing on a bumpy ride. I am surprised they would like Clark’s, as they are a go to favorite of mine as they are usually right comfortable!
    If one is trying a heel for the first time, I would steer them toward a Mary Jane or ankle bootie. They go with a right many things and offer additional stability while you get past your fawn legs stage.
    DSW and Nordstrom Rack offer an impressive variety in larger sizes and they are all out in the open so you do not have to ask someone to go and fetch your size.
    If you opt to try them on in a fitting room, the larger handicap rooms sometimes have a door that extends lower or offer room to put them on where your feet are not visible under the door. ; ). That was my trick for years before getting out and just trying them on in the aisle like other women.
    Norah

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    Replies
    1. AnonymousMay 15, 2025

      Norah, You have Uggs right?

      Delete
  2. AnonymousMay 14, 2025

    Once upon a time in a far away lifetime I sold women’s shoes. Here in Chicago back then every Halloween was the female impersonator ball. We carried large sizes. CDs would shop there. Some sales people refused to wait on them. I worked on commission no matter who purchased them. My last pair of heels were from the bargain store. Walked in boy mode removed my sandal tried them on and purchased them. No ones business what I buy. People will talk about you anyway!

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  3. Never tried, but I would have to imagine stilettos in desert island sand would be difficult. I don't know how Ginger did it....

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    Replies
    1. Hi Fiona, that's very funny! But imagine sand in your stilettos...ouch!

      I recall back in the day when people would debate who was more attractive: Mary Ann or Ginger? Instead, I was wishing I could *be* either one of them, or maybe even a combination of the pretty tomboy and the glamour queen.

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    2. AnonymousMay 15, 2025

      I vote to be Ginger with heels Hugs Brenda

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  4. AnonymousMay 15, 2025

    Another thing to consider when buying heels is some manufacturers but not all make the heel higher on larger sizes to maintain the proportions of the design. So on some brands you may find a 4” heel on a size 7 is a 4.5 “ on a size 12.

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  5. Thank you for this wonderful article with so so much great information! This line really sums up my experience: "Once your foot has entered into the shoe, the brain already starts shifting quickly into feminine mode." And a few years after my first experience in heels, when I was able to gracefully walk and dance in tall stilettos, I knew that I had made it.

    The article also brought back my own Payless memories, back when I would try on shoes like I was in the pit crew of the Daytona 500, taking off my boring shoe, slipping my foot into a heel to check for fit, and then back into my boring shoe in a few seconds flat. On one memorable occasion, a sales associate noticed my stocking foot and commented "you came prepared", then gave me the privacy to take a few steps in the shoes. Near disaster turned fabulous experience and a new pair of shoes for my collection!

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  6. I'm curious if anyone else has ever had this Cinderella issue with heels. When I wear a pair of my heels with hosiery, my foot slips right into the shoe and life is beautiful! But when I try to wear those same shoes barefoot, it's like I've suddenly become the ugly stepdaughter and my fat feet don't fit.

    Oh well, I guess I'll always have to wear hose;)

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    Replies
    1. Hosiery makes a big difference. The only catch is that hosiery also makes it easier for the shoe to remove itself from your foot unexpectedly especially if the shoe has stretched out after repeated wearings or if the shoe was a little larger than your actual shoe size (been there, done that, LOL).

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  7. AnonymousMay 15, 2025

    My first adventure of buying a woman's shoe was at a Sear's surplus store. I wore them until they feel apart. Back in the dark ages of the 1970's I was not comfortable buying a woman's shoe. Fast forward some years and I discovered Payless. I used the ruse of assembling a Halloween outfit. I bought pair number one at a nearby Payless and was offered their discount of 50% on a second pair. I balked as, if I did buy another pair, it would be obvious I was a cross dresser and not just goofing off for Halloween. I spent the day traveling to many Payless stores and buying one pair. When I found the size and the style that fit at Payless it became easy to buy and have shipped to home. I still have the results of a great Veterans Day sale packed away; five pairs of heels in their original boxes. How did Payless know veterans like me would welcome that great sale? I did some buying on ebay once I knew more about sizing. One critical aspect of buying women's shoes was the toe box: no narrow pointy toes for me. My favorite pair for strolling in a safe neighborhood is a black wedge with a low rise and a rubber sole which is great to avoid the head-turning clicking of a heel on a sidewalk.

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  8. AnonymousMay 15, 2025

    Real femulators wear hosiery...stockings preferred unless you need a tummy tuck then go Pantyhose.....Brenda

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  9. AnonymousMay 15, 2025

    I would say Payless was the Femulator and shoe fetish store of choice but a real pair of leather shoes is the wise investment. A classic pump from Nine West is the way to go. Leave the Crocs at the beach please and do not wear to run errands please

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