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. 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,


Like What You're Reading?

Share it with your friends!



I think you should dress in what makes you feel good! No need to wear granny panties when. You can wear the XDress lace briefs! Dress in what makes you confident no matter what age you are!


I love this site! My bf told me about it. I’m so excited for us to do some shopping!


I mostly like to think of myself as far younger than my real age. My favorourite clothing is a form fitting strappy camisole and either verys short micro skirt or ultra short girls running shorts and white knee high socks. I am not really into bras, as I think camisoles look great on men or women just as they are. i do like the ones with adjusters like Xdress sells, as it adds that extra bit of femminine, and I like the way the adjusters can be seen thru a t-shirt. I do like the look of the satin yoga set on xdress. maybe try that next.


I sort of got cut off on my last comment.
Growing up in the fifties and sixties was a wonderful formative time for me and that is how I would love to dress. However,now I mostly just wear panties and bra as well as a black or blue denim skort and tee going out. I wear ladies strappy open sandals and nowadays don’t try to pass as female , but rather just as a guy in a skirt.
I have pierced ears and long hair which usually is in a pony tail style. I am very lucky to still have a full head of hair and it is naturally wavy/curls.
O.K. That’s it for now I guess.
Thank you all and hope you all stay safe and well.


Hi Again.
I would just like to know how many miss the days when women dressed in skirts and heels. It just seems to me it is us guys now who have to keep the feminine look going. OH I understand the "me too "movement and all that but wasn’t it nice back in the fifties when if a woman was wearing a dress or skirt one could be certain she was wearing nylons and a garter belt , not to mention ,most likely, white panties.
No wonder so many of us fell in love with the desire to look and feel so wonderfully feminine and downright sexy.
I also miss the sweet sound of high heels clicking along on a sidewalk or hard floor. One could be certain of the treat of eye candy as a skirt and nylons were most assuredly about to come into view.
I loved seeing a flash of bare skin above stocking tops and if lucky a glimpse of smooth white panties as the breeze lifted a cute skirt .


Leave a comment

Please note, comments need to be approved before they are published.