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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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



I wonder if anyone else like wearing French Maid outfits?


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,


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


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.


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