Dressing Your Age

Dressing Your Age

Greetings to you, dear readers. I hope life is progressing well for you. Have you noticed that life as a crossdresser is a journey? It certainly is for me. The further I go, the further I have to discover things about myself – all things good, I’m happy to report.

So today, I’d like to discuss age differences in who we feel ourselves to be. What age do you feel yourself to be in your crossdressing life? That may seem like a weird question but think about it. Do you feel yourself to be a young girl? Did you perhaps start crossdressing by wearing your sister’s bras, panties, and skirts and other things? You know – the frilly socks, Mary Jane shoes, the schoolgirl uniform with a skirt and blouse, like the Teacher’s Pet Uniform from Xdress you can see here.

Some of you, I know, remember how luscious it was as a young boy to fantasize about being a girl in those wonderful school uniforms, training bras, and panties. Don’t forget to add some nice black stockings, like the Simple Seamed Stocking you can see here. If you like, you can go to a brick and mortar store and find thigh-high hosiery. Or, if a bit more daring, try a garter belt with the hose. XDress has several choices. So, do you see yourself as a young girl dressed in those innocent clothes of a prepubescent girl?

On the other hand, you might have started your crossdressing life by wearing your mommy’s clothing. My mom had a pair of shoes I loved. They were penny loafers cut so cute. They fit me perfectly, and I asked her if I could wear them. She was fine with that, and I wore them a lot – even in public. I tried her high heels, but they didn’t work for me. Maybe they do for you, and you can find men’s-sized shoes at XDress here. I am partial to the Sexy Ballet Flats, as heels don’t work for me, as I already said, but perhaps they will work for you. All the shoes are really attractive – I just wish I could wear them all!

Having taken to my mom’s clothing, I am particularly drawn (given my age) to the 1950’s housewife dresses. Think Donna Reed, if you are old enough to remember her –the housewife full skirt and dress kind of look. Of course, you must also wear proper hose and shoes, as well as a corset. You can find proper corsets from XDress here. How could we forget wearing a proper bra with proper housewife clothing? Go here to see some wonderful examples of bras that fit just right for our gurly build. It’s also a lot of fun to go shopping in a brick and mortar to find other bras and panties. I should know – my wife has bought more of my bras and panties for me than I have!

On the other hand, some of you may prefer the Goth look. What led you to that? Why do you prefer black everything, including nails, makeup, and clothes? What led you to that?

So, what is your preferred age and style of clothing? I personally prefer an age-appropriate dress, given my great admiration for my mom and wanting to look like her. Perhaps yours is younger or edgier? Warm-up that keyboard and tell me about your age/style preference. As you know, dear readers, I love to hear your stories.

Fond regards,


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I am much older and have dressed up in age and down in age .I prefer much younger.


Hi everyone
Wear something pretty today i am!
What a great topic
I started with high heels and pretty feet. From there it progressed
I m in my 50s so i probably dress more 35 ish
Skinny jeans stillettos matching bras and panties
Pretty toe nail polish
Light make up
Now if i could go out sometimes i d wear that or a pretty knee length dress pumps occasionally stockings (thigh high)
I do the love the business woman look and the 50s look
Glad so many others are out there!
It s great to know we are not alone


Hi Angie. This is a great topic. My favorite look is the career women look—age range from the late 30’s to late 40’s. Since I am in my early 50’s I can still get away with looking a little younger. Black pencil skirt with a matching black jacket and a white blouse. Add in black panty hose along with 4" black high heels. Light make-up and long wig pulled back. I recently started wearing black frame unisex glasses which completes the look. I probably adopted this style from my mother who actually started me on my crossdressing. Interested in hearing more in this conversation.


Hi Angie

Another wonderful blog, which takes us back to the moment when it all started.
As I already wrote here, from a very early age I felt like a woman, but it was only when I was a teenager that I really preferred to be a woman. At the beginning in the usual games for kids, I always assumed the role of a girl, I timidly started wearing white or pink panties with bows and flowers or dolls. It was with the lingerie of my first boyfriend’s mother that marked my style. She had beautiful lingerie and was a very beautiful woman. The style I like is a modern classic!
Depending on what to wear I like Brazilian underwear or thong. The bra used in the sports house are the only ones that fit us well. I still can’t move to another level, my professional status doesn’t allow it. I know Xdress very recently, but I hope to debut on a purchase with you soon.
Congratulations on the blog.


Angie – you cut right to where I come from. When I was 11 in Catholic school, I was sat a a group of desks with 2 girls, Lisa, and Maryann. The first thing they said to me was that this group was for girls only and that they were going to make sure I dressed like them. Of course, they never did, but they talked about it all the time, which got me thinking about it more and more. So much so that I did begin to explore my sister’s things. She was a year younger, and we were close in size, so it seemed natural to try on her plaid skirt and white blouse and knee highs. Of course, I included her training bra and a pair of white nylon panties with little blue flowers on them. After that, I was hooked and tried her things whenever I could. To this day I still prefer to wear the clothes of that innocent, prepubescent girl just as you described. Thanks for the blog.


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