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,

Angie

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42 comments

I would like to wear more feminine outerwear items as well as panties and camis, but I don’t think I would pull it off (I am 6ft 2" and in my 40’s and reasonably well built). I do wear short womens althletics shorts and leggings, and recently have fallen in love with very short cap sleeve T shirts with wide necks. These show my muscular arms and chest off well, and I really don’t know why these aren’t made for men (hint to bodyaware) My back yard is reasonably private so I can wear these there, and have occasionally run out to the mailbox, but only under cover of darkness. So I would say my dress age is late teens or early twenties. My wishlist would include a short miniskirt with knee high white socks, mary janes and a strappy bra top under a cropped cap sleeve T.

Peter

Dear Krystin
Thank you for the encouraging words, I m not trying to pass either but love the femme fashion
Underneath and unisex looking jeans will have to do for now, lol
I hope for the day when a man in heels is just a different fashion choice
Stevie
Wear something pretty today
I am

Stevie

Hi Stevie,
Yes, I live in a large city and there are various places I can go without any hassle. Some are LGBQT friendly and others are not, but they still are very accepting. As I mentioned in an earlier post, I usually dress androgenously but with definite femme emphasis, though I couldn’t pass as a genetic girl and don’t really want to. Thankfully my GF not only supports me but is actively involved with my dressing, giving me advice on outfits and makeup. Also, most of my co-workers are women and they are on board with my dressing, which I usually do a couple of days a week and on special office functions

Still I can relate to your wanting to go on a dressing binge. Sometimes I feel like doing the same thing and actually trying to pass as a woman. Maybe someday soon crossdressing will be just another kind of fashion choice and people will hardly notice. Until then, wear something pretty underneath!!

Kyrstin

Hi nathan angie krystin
I envy those of you that can dress how you want where u want
Is there anyplace that you know of where a person could go on a dressing binge? Just asking because the desire is so strong for some of us and its almost painful sometimes
Sometimes the underdressing isn’t enough
Wear something pretty today, I am: pretty tan/ brown nail polish with black cotton brazillian cut panties
Stevie

Stevie

I agree with Stevie and Kyrstin. Most of the compliments come from women but men do occasionally show interest as well. It’s such a wonderful feeling isn’t it? To me it makes me feel so much more confident!

Today I’m wearing a classic; leather skater skirt with black hose, a plain black tee and 5" heeled boots. It’s such a cute outfit! Keep the comments coming, this is a great conversation!

-Nathan

Nathan

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