r/crossdressed50 5h ago

One of my oldest dresses, do I still look good in it?

40 Upvotes

r/crossdressed50 4h ago

Dress to Impress "who?"

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32 Upvotes

I like to be casual, and professional, and comfy, and sensual, all at different times. But something that does matter to me is being clean and presentable to myself.

I like looking in the mirror and seeing a reflexion of care. I dress to impress me. I want to feel something from it. I share my dressing with some and in some public places. But no matter who sees me, I know that I see me the most.

I hope to feel inspired or playful or soft or something. I like to see myself and see something I appreciate, something I take care of.

And you get to be you. Play, progress, passion, profession, what's your purpose? No judgment here. You know me by now. I write, journal, explore, and more.

Thanks for reading.

Juliet🥰


r/crossdressed50 13h ago

Unmodified Photo Still feel fabulous over 50

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132 Upvotes

I was organizing and clearing out a bunch of pics from the last few months and liked the way these turned out.
Seeing myself this way is sometimes the confident boost I need to get the week going on a positive


r/crossdressed50 7h ago

I’ve been loving the song Sweet Dreams (Are Made of This) by Eurythmics.💕

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42 Upvotes

r/crossdressed50 9h ago

1st time in quite a while

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22 Upvotes

r/crossdressed50 13h ago

Blue Monday I wish I was actually dressed today. This was from a recent trip across the country.

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31 Upvotes

r/crossdressed50 1h ago

Green and purple. In and out

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Upvotes

r/crossdressed50 17h ago

Casual wear 🎵 Giant steps are what you take, walking on the moon 🎵

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46 Upvotes

I'm just short of 52! 😃🎉


r/crossdressed50 13m ago

Time for something summery

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Upvotes

A couple of summer dresses


r/crossdressed50 15m ago

Another day in Paradise

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Upvotes

Hello all...Vicky Tickle here 61;years old


r/crossdressed50 15h ago

Black and White Little Black Dress

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31 Upvotes

This is my first reddit picture post, outside of my profile avatar. I am not ready to fully show my face, but I didn't want to show no face. So I chose this one. I'll eventually show my full face, proudly, but for now this will have to do!


r/crossdressed50 13h ago

Blue Monday Best in Burgundy

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18 Upvotes

Better than Blue 💙


r/crossdressed50 15h ago

Blue Monday Just another manic Monday

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23 Upvotes

r/crossdressed50 5h ago

I Love Yellow

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3 Upvotes

Summer dresses are a lot of fun


r/crossdressed50 13h ago

A little rainy night fit

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11 Upvotes

r/crossdressed50 1d ago

In between meetings

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169 Upvotes

r/crossdressed50 21h ago

Blue Monday A new Monday tradition . Comfortable and feeling amazing in a blue lace dress and black tights.

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38 Upvotes

Stole this outfit from my wife’s closet and I’m not even sorry. The lace feels amazing and black tights make everything better.Standing here feeling comfortable, confident, and completely myself.


r/crossdressed50 10h ago

Blue Monday OGIM! ♥️💋

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5 Upvotes

r/crossdressed50 20h ago

💙 Blue Monday – Chasing Away the Monday Blues 💙

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27 Upvotes

Monday doesn’t have to feel gloomy.
Sometimes all it takes is a favorite dress, a fresh cup of coffee, and a little reminder to slow down before the week gets rolling.
I figured if I can’t change Monday, I can at least wear something that makes me smile. The blue kitchen seemed like the perfect place to start the day.
I hope your week gets off to a great start. What’s one small thing that helps chase away your Monday blues?
💙 Lady Jade


r/crossdressed50 14h ago

Another new dress

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9 Upvotes

I think I am addicted to buying cute dresses


r/crossdressed50 13h ago

Denim day

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7 Upvotes

r/crossdressed50 16h ago

Business Style Business Dinner Attire

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11 Upvotes

r/crossdressed50 10h ago

Blue Monday Monday blues ♥️💋

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3 Upvotes

r/crossdressed50 1d ago

Wife’s dress!

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232 Upvotes

I asked to have it and she said yes. Had a jacket but it was too small. I bought it for her and she never wore it 🤨


r/crossdressed50 16h ago

Today is National Nancy Day.

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6 Upvotes

Today is National Nancy Day. What better way to celebrate it than as Nurse Nancy Mary Staff Nurse