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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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!



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!!!!!


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