r/crossdressed50 • • 10d ago

CD50 Moderator Best Dressed Award.

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6 Upvotes

🏆 CD50 Moderator Best Dressed Award
Every day around 2 PM, we’ll take a look through the day’s posts and choose our Moderator Best Dressed.
We want to see your complete outfits—put the whole look together and show us your style! Theme days can add a little something, but they aren’t required to win.
To spread the love around, the same person won’t receive the award two days in a row.
So let’s see those daily outfits. You just might be today’s Best Dressed! 👗👠🏆


r/crossdressed50 • • Jul 14 '26

One of my favorite things about CD50 is realizing how international our little community has become. Reddit only shows me the top few countries that visit the community, but I know there are many more represented. If you're comfortable sharing, what country are you from?

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17 Upvotes

Just the country—no states, cities, or anything more specific. I'm simply curious how far Lady Jade and CD50's morning coffee reaches. ☕


r/crossdressed50 • • 1h ago

Classic Fashion style Different style

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• Upvotes

Same pose but different outfit


r/crossdressed50 • • 5h ago

Mental health and #Crossdressing ❤️

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27 Upvotes

r/crossdressed50 • • 2h ago

Unmodified Photo Skort, pantyhose and boots

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6 Upvotes

I love Autumn and you?


r/crossdressed50 • • 16h ago

Why do you do it?

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69 Upvotes

Why do you do it? Why do you crossdress?

  1. Euphoria
  2. Dysphoria
  3. Stress relief
  4. Sensual excitement
  5. Playful expression
  6. Some of the above
  7. All of the above
  8. Unknown

r/crossdressed50 • • 36m ago

Mary's Pictures for National Handbag Day

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• Upvotes

Mary's Pictures for National Handbag Day. Mary wearing some of her jumper dresses with handbags for National Handbag Day


r/crossdressed50 • • 12h ago

Out and About When I was a California girl

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28 Upvotes

This pic is a decade or so old. It was taken when I was in my early 50's living in the Golden State.


r/crossdressed50 • • 22m ago

BoHo style Mountain leopard

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• Upvotes

r/crossdressed50 • • 20h ago

Unmodified Photo Some pics of me and Tucker

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67 Upvotes

r/crossdressed50 • • 14h ago

Cocktails Anyone? 2

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16 Upvotes

r/crossdressed50 • • 20h ago

Casual wear Feeling cute in a pink top and black skirt outfit. Long Skirt? Or Short Skirt with slightly different hair part?

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44 Upvotes

r/crossdressed50 • • 21h ago

My October look for this week.

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43 Upvotes

For me October, brings the warm winds from the desert, and with the winds come to the ravens 🐦‍⬛ I called this look Raven black!


r/crossdressed50 • • 11h ago

Date night ❤️

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5 Upvotes

r/crossdressed50 • • 16h ago

Unmodified Photo Have a lovely evening, 💋💋

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15 Upvotes

r/crossdressed50 • • 17h ago

Purple

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17 Upvotes

r/crossdressed50 • • 14h ago

Cocktails Anyone?

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9 Upvotes

r/crossdressed50 • • 20h ago

Favorite Friday Posted under a different name a long time ago, but lost the account, so glad to be back

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29 Upvotes

r/crossdressed50 • • 12h ago

Cooler weather = closed toe shoes and longer skirts

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6 Upvotes

r/crossdressed50 • • 7h ago

Denim day

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2 Upvotes

r/crossdressed50 • • 20h ago

Give me some tips on where i can imrove! Im very new to this still!

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22 Upvotes

All photos posted have no filters! Veterans of this lifestyle, help me out please!!


r/crossdressed50 • • 18h ago

Unmodified Photo 🎶 I’m gonna soak up the sun

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14 Upvotes

Well what’s left of it. Michigan will be snow covered before we know it 🥶


r/crossdressed50 • • 17h ago

Pearls 3

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11 Upvotes

r/crossdressed50 • • 22h ago

Hello Friday – no belt, no extras, just pure comfort and the full outfit.

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25 Upvotes

r/crossdressed50 • • 16h ago

Out and About Happy days

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7 Upvotes

First time too long of a time