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. I am partial to flats, as heels don’t work for me, as I already said, but perhaps they will work for you. All 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,




Oh definitely girls are more accepting by about a 3:1 margin I’d guess. Most of those sideways glances I mentioned were from guys, but I’ve also had positive comments from a few males too. I wondered if they were secretly wearing panties haha!

Kyrstin March 04, 2020

Kyrstin, I wonder if its more girls than guys that give you compliments? Generally I find girls are more accepting

Jase March 03, 2020

It’s fun to read all the styles each of you enjoy wearing. I can get away with a sort of feminine leaning androgynous look at work, 2” heels/boots, skinny jeans, light makeup, that sort of look. Weekends out with my GF, I tend to be a bit bolder, with mini skirts and 4” pumps along with a femme top and jacket. We’ve got a few sideways looks but no one has ever been rude, and I’ve even received a few compliments!

As Stevie says wear something pretty today!

Kyrstin March 03, 2020

Just a further comment I wish I had come of age now in my day I would have been run out of town for crossdressing .Actually my ex told my children I liked to dress I have never confirmed or denied its no ones business and again young girls frills and ruffles will forever be my favorite its such a sweet place to be

micki March 03, 2020

I wonder if anyone else like wearing French Maid outfits?

Sallie March 02, 2020

Hi all. What fun responses! It seems like we are all over the map, from the “fabulous 50’s”, to school girl uniforms, to the more mature and looser fitting look, and of course not forgetting the more edgy Goth look. A couple of you commented on pencil skirts, and thank you for that. I think pencil skirts are about the sexiest skirts out there. I learned that on me, a missy cut gives that form-fitting style that pencil skirts are so well known for. Keep those comments coming – this is a lot of fun to read!

Fond regards,

Angie March 02, 2020

Hi Gurls
I think it’s more important to dress your shape rather than dress your age. If you are sixty and slim and look great and feel comfortable in a micro-mini dress and heels then good for you. If a looser and longer style with lower heels makes you feel good, then good for you too. Elegance is everything. I go with a more relaxed and mature style now. My days of squeezing myself into something short and wobbling on high heels are over I’m afraid.
Whatever you do though, just enjoy it. If you’re young then make the most of the time you have to practice. You’ll get more confident as you get older.
Ally x

Ally March 01, 2020

I’m with Mikki, dress me as a schoolgirl or in a frilly party dress and I’m in heaven. Influenced by having 2 sisters growing up, always liked girls clothes more than boys. Probably like all prepubescent boys, I was fascinated by what colour panties girls wore and not until I got away to college did I start getting my own panties, and never looked back. I would never dress in public, but as I live alone, I am able to dress up in the privacy of my home and imagine being a schoolgirl. My fantasy is being the only boy in a girls school and finding out on my first day that only schoolgirl uniforms, gymslips and ballet leotards are available.

Petie February 29, 2020

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

mikki February 29, 2020

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

Stevie February 27, 2020

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.

Randy February 27, 2020

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.

Nuno February 27, 2020

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.

Michael February 27, 2020

Angie, this a great blog. Your admiration for that secretary look is definitely shared amongst us all, I imagine. There’s just nothing like a pencil skirt and satin blouse paired with stockings and heels. I can never take my eyes off my girlfriend when she wears the style (or any other, for that matter).

Your mention of the goth style definitely needs a response from me, so here goes. I would say what led me to the style is my personality. I’ve always been antisocial, and had an attraction to things of the occult / sinister nature. Combining that with my inherent femininity, and voila! Goth is my style and always will be.

In regards to the all black everything, black just appeals to me most, especially in materials such as velvet, satin, lace, leather, and PVC. Even if you’re not a Goth, it’s hard to argue against the allure of black in these materials.

As far as dressing my age goes, I do exactly that. Mini skirts, 4" heels, and very feminine tops are my favorite. This suits me well since I’m still in my early 20s and I have a slim body. There isn’t a specific person that inspired me to dress like this, it’s just who I am.

This is an amazing talking point and I can’t wait to see the conversation develop!


Nathan February 26, 2020

Yes,you are so right the 50’s Donna Reed style is fabulous. That’s why it is referred to as the fabulous 50’s I love the sexy secretary,corporate queen look; tight pencil skirt,satiny blouse,sheer black stockings and a beautiful stiletto heels. The beautiful sound of the stiletto heels clicking in the office PRICELESS!!!!!

Sallee February 26, 2020

Leave a comment

All comments are moderated before being published