crossdressed50

A place to discuss dressing, passing, and constructive criticism for the 50 and above ladies. We want to see your complete outfits. Share your photos but please, let’s keep it clean & classy. Post as many photos as you like… NSFW photos WILL BE deleted. All pictures must be SFW.

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Hello everyone. Just a reminder for everyone. Remember that Crossdressed50 is about the fashion and passing in public.

Posted 15th May 2025u/Lady_JadeCD

Just kept twirling in it....haha💐 🌹 🌸 🏵 🌼

Posted 11th May 2026u/AmandaTaylor8

Open to work. Would you hire me?

Posted 11th May 2026u/LadyMichelleDeluxe

Almost 60....had to give my feet a break from the heels😁😝

Posted 11th May 2026u/OriginalTax149

The other dress

Posted 11th May 2026u/Glittering_Carob6272

Just a CD chick over 50 in a car trying to be hot

Posted 11th May 2026u/nyalared

Welcome to a new week.

Posted 11th May 2026u/Lady_JadeCD

Posted 11th May 2026u/Glittering_Carob6272

Monday Blue .I think for me, elegant clothes will never be boring. 👗

Posted 11th May 2026u/LopsidedStatement517

I think wrap dresses are still in style

Posted 11th May 2026u/carriebtv

Posted 11th May 2026u/old_Dee

Posted 11th May 2026u/Sweet-Apple-1562

Posted 11th May 2026u/Glittering_Carob6272

Mother’s Day 2026

Posted 10th May 2026u/KatherinefromCali

Posted 10th May 2026u/Ka8tie_Mac

Make up 4 months experience 🤣.Its so fun

Posted 10th May 2026u/Sunny-licks

Black velvet dress 🖤

Posted 10th May 2026u/amber_gemstatediva

I need some color, lol... xoxo

Posted 10th May 2026u/sian_xoxo

Up all Night, didn't change back until the sun came up!

Posted 10th May 2026u/Gandalf4052

Little red dress.

Posted 10th May 2026u/Marmissure

Mature Latina cd

Posted 10th May 2026u/BitEquivalent8917

Posted 10th May 2026u/Piercedmilkman

Happy Mother's Day to all the Wonderful Mom's and Domestic Goddess's

Posted 10th May 2026u/CrossDressPhotog

My mother’s day look. Thinking of Grandma, dressed in one of her church clothes.

Posted 10th May 2026u/LopsidedStatement517

I’m going to try everything. It’s made my life fun .

Posted 10th May 2026u/Sunny-licks

Hello Sunday. This one happens to be Mothers Day. So don’t forget to wish the mothers in your life a Happy Mother’s Day.

Posted 10th May 2026u/Lady_JadeCD

Simple Sunday dress

Posted 10th May 2026u/carriebtv

Trying to look like a normal woman

Posted 9th May 2026u/Rachel_Elizabet

Blazer and spanks

Posted 10th May 2026u/KatherinefromCali

I stopped wearing men’s cloths 4 months ago .Not one family member stayed with me

Posted 10th May 2026u/Sunny-licks

My just crawled out of bed look .

Posted 10th May 2026u/Sunny-licks

Which tights do we prefer? Think I'm team black 🖤

Posted 9th May 2026u/Lets-Share-Together

“Cute enough to distract you.”

Posted 10th May 2026u/Superb-Bat6721

Constantly missing dressing!

Posted 10th May 2026u/mjryo

Summertime dress

Posted 9th May 2026u/amber_gemstatediva

Saturday makeup look

Posted 10th May 2026u/ChristyAustyn76

Posted 9th May 2026u/EyaelHeze

Took a chance with this outfit. What’cha think?

Posted 10th May 2026u/secretcd13

That weekend feeling

Posted 9th May 2026u/DelicateFrosting73

New skirt ❤️

Posted 9th May 2026u/TaylorRouen19

Posted 9th May 2026u/Piercedmilkman

Another day another dress🤷

Posted 9th May 2026u/Aggressive_Mix6094

LBD is always a wonderful choice.

Posted 9th May 2026u/LopsidedStatement517

Hello Saturday morning. What’s the plan for the day?

Posted 9th May 2026u/Lady_JadeCD

50+ love dressing

Posted 9th May 2026u/Girlyhubby

Saturday casual

Posted 9th May 2026u/carriebtv

Enjoying the warmer weather today.

Posted 9th May 2026u/CDmichelle68

Showing 47 posts out of a possible 50.
3 posts hidden as gallery mode enabled.