Wednesday, May 21, 2025

Payless Revisited

The recent discussions here about high heels and Payless moved me to see how many pairs of Payless shoes I own. I knew I had a lot, but was surprised to discover that I owned 47 Payless pairs!

When I was still gainfully employed, I had a Payless store nearby my workplace that I could haunt in boy mode during my lunch hours. Whenever I did so, I swapped my socks for a pair of knee-highs before I visited the store so if I tried on women's shoes, I would get a better idea how they fit.

On my first Payless visits, I would buy a pair of shoes, take them to my car and try them on to see if they would fit. I was not concerned that the Payless staff knew that I was buying the shoes for myself. I was more concerned about freaking out another customer seeing a guy trying on gal shoes.

Trying on 4-inch stilettos in my Subaru got old fast, so after I became familiar with the Payless staff, I asked if there was a better way. The saleswoman I spoke with suggested I use their back room to try on shoes and that’s what I did for awhile. 

But eventually I said “damn the customers” and I began trying on shoes out in the open. I seldom ran into another customer while trying on heels because I was shoe shopping in the lonely aisle that had women’s sizes 10s, 11s, 12s and 13s.

One day off from work, I visited the store en femme and the saleswoman happened to be one I dealt with in boy mode many times. The way she greeted me on the way in was not the way she greeted me in boy mode, so I assumed she was clueless about who I was.

After finding shoes to purchase, I took my finds up to the register and she still acted like I was just another random female customer. I had to say something, so I said, “Remember me?” 

She looked at me more closely and then the Oh-My-Gods began. She said she was clueless and would not have recognized me if I had not spoken up. She also added that I passed with flying colors.

And so it goes!



Image Source: Rue La La
Wearing 1.State


RuPaul Charles
RuPaul Charles femulating in The Brady Bunch Movie.

9 comments:

  1. "Pass with flying colors" - my all time favorite phrase to hear.
    "Hey Mister" - my all time LEAST favorite phrase to hear.
    And yes, I really miss Payless. :)

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  2. AnonymousMay 21, 2025

    I sooo miss Payless as crossdressers we were lucky to have a store that had a large selection of inventory in higher sizes and cute also. I remember knowing exactly were every Payless store was located. My Payless story was trying on a pair of 3” heels in male mode as I stood up and walked in them the middle age lady that was working at the time just looked at me in disbelief and started to laugh I guess she had a good story to tell over dinner. Jill

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  3. This made me smile. I don’t have 47 pairs (yet!), but I totally get the appeal of finding heels that actually fit. I’ve definitely done the whole “quietly wandering into the size 11+ section” thing more than once.

    And that moment where she didn’t recognize you en femme until you spoke? That’s the kind of validation we dream about. It’s funny how we brace for judgment, but people are often way more chill than we expect.

    Thanks for sharing—this was such a cute little win.

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  4. 47 pairs just from Payless? I've got shoe envy!! I'm curious how many shoes you have in total.

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  5. AnonymousMay 21, 2025

    Re: your Payless visits--it would be great some time if you could comment on your interaction with women in general.I have found that the Payless clerk was not atypical . Most women do not seem disturbed by us but rather "welcome aboard".
    Men--not very much. What is your experience and more importantly if you agree with me why is this so in your opinion? thanks--Emily

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  6. AnonymousMay 21, 2025

    Shoes seem to have a strange effect and elicit more conversations than one would expect. I’ve noted more conversations with other females in the shoe aisles than anywhere else in a store, and the till clerks never fail to comment on whatever shoes you buy.
    Norah

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  7. AnonymousMay 22, 2025

    Well, I've less than 20 pairs of shoes from all sources, but enough for all occasions. However, I do have 25 bras, at least a third given by woman friends. For me a pretty bra , even if invisible to the world is one of the most important parts of being me.

    Lily

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  8. I guess I am only a piker with only about 10 pairs of "women's" shoes. However, I have about 48 dresses. Pants (trousers) ? I haven't worn them since my mother's funeral in 2024 late September. I notice not many women wear heels anymore.
    John

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  9. Payless... :)

    Payless was one of the first places where I started feeling safe to crossdress openly. I would ask the employees if they had a lot of customers like me. They would normally answer, "Yes, a few, but the others go all-female with make-up and a wig."

    I would often shop in the store in all male mode or eventually in a skirt. The employees treated me like I was welcome and normal. Once, I was trying on ladies shoes with an employee's help. I was wearing men's shorts with pantyhose. I was shocked to find out that the employee had not noticed my pantyhose. I was trying on heels while she watched from five feet away. She hadn't noticed! I was SO stressed out that day, walking around a mall wearing pantyhose and shorts. I think that helped me realize that "if she couldn't see them while looking at my feet in heels, then maybe most people won't see them."

    These days, I go to Shoe Show. They have larger-sized women's shoes. They are affordable. However, it is not as nice to shop there as it was at Payless. I don't know why.

    For the group accounting, I own ~5 pairs of shoes, ~5 dresses, ~10 skirts, and ~20 pairs of pantyhose. I take rarely-worn clothes to the thrift store. I do not wear hose enough to wear them out, apparently. Some brands (mostly Leggs) last 10+ wearings. Yet, I sometimes see hose for sale and think, "Ooh, I should try those," or "I should buy those since they have my preferred style that are becoming hard to find!"

    I loved your story, Stana. It made me happy for you when she said you passed. That must have been a dream come true! :) FYI: I am having trouble with my e-mail account right now. I have two yahoo e-mail addresses. One is my verification account for the other. Suddenly, both are asking me to verify via the other account. Hopefully, it will open up for me. For now, I am hard to contact...

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