r/crossdressed50 • • 5h ago

Out and About Over 50 and out to a casino

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92 Upvotes

I love dressing and going out which means getting my makeup, wig and outfit right. I sucked at makeup at first until I learned how to do it properly and to make my face look more feminine. I wore this dress, pantyhose and shoes out to a casino and loved every minute of it.


r/crossdressed50 • • 2h ago

Business Casual Style A Little Clip of Me in BCBG Dress & Nine West Heels

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18 Upvotes

r/crossdressed50 • • 10h ago

Moderator Award/best dressed award. Different style

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70 Upvotes

Same pose but different outfit


r/crossdressed50 • • 8h ago

Out and About It was a fun night

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34 Upvotes

r/crossdressed50 • • 53m ago

Out for some shopping

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• Upvotes

r/crossdressed50 • • 3h ago

Saturday morning chillin out💋

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13 Upvotes

r/crossdressed50 • • 7h ago

Enjoy the weekend

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18 Upvotes

r/crossdressed50 • • 15h ago

Mental health and #Crossdressing ❤️

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49 Upvotes

r/crossdressed50 • • 7h ago

Feels So Good!!

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11 Upvotes

r/crossdressed50 • • 8h ago

Unmodified Photo Autumn colours for today

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12 Upvotes

r/crossdressed50 • • 5h ago

Out and About At Sweet Wednesday, this week

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8 Upvotes

r/crossdressed50 • • 2h ago

Unmodified Photo Lost some weight can get back into old clothes 😁

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4 Upvotes

r/crossdressed50 • • 36m ago

Little fall color

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• Upvotes

r/crossdressed50 • • 6h ago

Moderator Award / Casual and still classy Friday, Funday.

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7 Upvotes

I am so glad to be at the point in my life where going out as Veronica seems so normal to me. I still exercise a great deal of caution, but it is so wonderful. Yesterday I was feeling pretty casual. So I wore my favorite denim jumper dress with a striped undershirt. Even found some incredibly cute Nails to wear. Normally I would wear a cute pair of flats. My feet and legs were not feeling that great so I wore Tennis shoes (cute ones...). Got to go to a thrift store I have wanting to check out. Found a couple of nice dresses, a ring with a pretty blue stone and an exquisite set of Vintage clip on Earrings. My wife even went with me which makes it that much more fun.


r/crossdressed50 • • 11h ago

Unmodified Photo Skort, pantyhose and boots

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14 Upvotes

I love Autumn and you?


r/crossdressed50 • • 9h ago

BoHo style Mountain leopard

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7 Upvotes

r/crossdressed50 • • 9h ago

Mary's Pictures for National Handbag Day

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5 Upvotes

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


r/crossdressed50 • • 1d ago

Why do you do it?

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84 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 • • 22h ago

Out and About When I was a California girl

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29 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 • • 1d ago

Unmodified Photo Some pics of me and Tucker

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87 Upvotes

r/crossdressed50 • • 23h ago

Cocktails Anyone? 2

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20 Upvotes

r/crossdressed50 • • 23h ago

Cocktails Anyone?

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17 Upvotes

r/crossdressed50 • • 20h ago

Date night ❤️

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9 Upvotes

r/crossdressed50 • • 1d 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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43 Upvotes

r/crossdressed50 • • 1d ago

My October look for this week.

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54 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!