Close this search box.

Jocelyn’s First Wig Adventure

Let's revisit our initial introduction to Jocelyn!

By Jocelyn Johnson

This is a rerun from the old blog and I left the original introduction in place because, well you’ll understand.

This post means quite a bit to me. It is the reason I keep doing this blog. I have recently considered shutting it all down, I do that often. The truth of the matter is, this is work. And it is work that I get paid nothing for. I get no direct human feedback, from real people in the real world. E-mails, comments, all wonderful, but they are virtual. But this is a labor of love. This place also apparently means something to some beautiful people. Jocelyn is one of them. She reached out to me through the “Contact” page on November 28 and here she is, sharing with out little community. She is a genuinely beautiful person and I am privileged to run this post.

Since getting back into crossdressing, after decades since a mid-thirties purge, I was contemplating the order of restocking my closet. Should it be shoes and a dress first, or get a wig and then go shopping for a wardrobe? I do not like shopping online since I prefer to see the item, try it on, and then purchase it if it all fits and the price is right. But a girl shopping for shoes and clothes with short grey hair is not good, but wig shopping in a dress isn’t a good look either. I also thought I could not go in a skirt, nor in regular jeans or slacks. So a few days before, I went to Walmart to look for some leggings; which I thought would be more feminine looking. I tried on various styles and sizes and eventually settled on maroon Jordache leggings. They look good on my legs, but I don’t have the hips and derrière to fill them out appropriately. Oh well.

I made an appointment at a wig store in a nearby Town that specializes in serving cancer patients and cosmetic customers. They do wig fittings by appointment only. So, Monday Jocelyn was to see a lady at the shop.

On Monday I got dressed in the leggings, a bralette, a sweater, flats, and a simple gold colored chain necklace. I only had foundation makeup on. I drove to Town, and because it wasn’t a cold day, I walked up the street like that carrying a pink wallet.

I was nervous when I approached the shop and went in. There were no other customers there and the shop owner was very welcoming and friendly. She asked if I was Jocelyn, and I was! My short grey hair was a dead giveaway that I was an “old man” looking for a wig.

We went to the back room and for the next 45 minutes I had a marvelous time trying different styles and colors of hair. The sales lady was quite helpful and she offered a few makeup tips as well. Her best advice was to color my eyebrows to match the color of the hair. When I looked in the mirror with the brunette hair, the grey eyebrows made the whole face look odd.

It cost quite a bit more than I hoped, but the quality is good. Of course I had to get a wig stand, shampoo, cleaner, and brush. And paying for it all on a credit card with a different name didn’t seem to matter.

This experience was my first, spending so much time with a stranger, and just being Jocelyn.

A few days later I took a number of pictures with my new hairdo. I’m not sure I made the right choice. Maybe the look will grow on me.

How lucky am I to make these connections, get to know beautiful people like Jocelyn?


6 Responses

  1. Kandi,
    The thought that I might have had even the smallest influence on keeping your wonderful blog going is extremely humbling for me.
    You have been a huge influence on me in my life as a woman. The biggest thing you have taught me is that “passing” is not the ultimate end for us. It would be great if everyone saw me as a natural woman, but my physical stature cannot be overcome with dresses, makeup and a wig. But what is important, is that society can see women like us and be accepting and welcoming. We are just making our way through life as best we can.
    It is my privilege to be a small part of Kandi’s Land.


  2. Jocelyn, I think that wig looks great on you. I recently bought a wig and wear it occasionally. I also have Grey hair, but it is long enough to style and I love the job my hairdresser does. The wig I bought is pretty much the color of my own hair. Good luck
    Yours Terri

    1. Terri,
      Thank you for the compliment. Your support means a lot, and helps verify my style.
      During COVID all the hair salons in Ontario were closed for over half a year. My grey hair grew long enough for me to think I could forgo my wig for an outing. I did spend an hour in the park with my friend Alison and I could have gone to lunch and shopping afterwards. But I just didn’t feel right with longish grey hair; it wasn’t me. So I called it a day and vowed never to go out again without my brunette wig.
      I guess I’m just old and stuck in my ways.
      Thanks again Terri.

  3. Great post, Jocelyn!

    I’ve always fancied the idea of going for a proper wig consultation rather than the hit and miss world of Amazon, online retailers and the local ethnic hair shops that I have frequented at one time or another. Problem is that the only place near where I live is more or less opposite a close friend’s house so I’m bound to get caught in the act! I’ve had some shockers in my time that can only be described as bearing more than a passing resemblance to road kill but you seem to have hit the jackpot with that one.

    1. Thanks Amanda. My wig hair is shoulder length, a slight wave, and combined with the brunette colour takes years off my look. It makes me feel young and attractive (relatively speaking).

      I went to the wig store with great trepidation, but determined to see it through. The 45 minutes I spent trying different styles and shades was fun and educational. You really should find a wig store in a nearby city where you can be comfortable. You’ll be very happy you did. But a good one is expensive.

      Take care friend.


Leave a Reply

Your email address will not be published. Required fields are marked *

Featured Posts

Get The Latest Updates

Subscribe To Our Newsletter

Sign up for the first look at Kandi’s outfits, blog posts, and product recommendations.

Keep Reading

More From Jocelyn Johnson