Kentucky Derby

[Jillcder]

Did anyone else watch the Derby? My goodness the dresses were incredible very feminine and pretty, I thought there has to be a few cross dressers in attendance after watching I put that on my bucket list maybe by then my wife will be on board and we both could get dolled up. I already forgot what horse won but I sure remember a few dresses I liked!

[Lisa516]

Derby winner Medina Spirit very nice dresses indeed.

[susanmichelle]

Yes to the pretty dresses. I saw a few ugly ones too lol. One of the main things too about the Kentucky derby is the beautiful hats most of them design themselves.

[BLUE ORCHID]

Hi Jill :hugs:, The Pretty dresses are the best part of the Triple Crown, >Orchid **O:daydreaming:O**

[Crissy 107]

The dresses are always wonderful, horses, what horses?

[alwayshave]

Jill, my wife loves Derby Day as a reason to wear a hat. Sadly I wear dresses more often than she does.

[Teresa]

Jill,
We have had a couple of Ascot Ladies Day meetings with my social groups they are a lot of fun , giving us a chance to wear lovely outfits with matching hats and shoes .

Last time it was being held at the same hotel as the blood donation session , I mentioned this when donating my pint so the nurses asked me to pop in later that day to show them my outfit . It was quite funny to see the looks on the waiting donors faces when I walked in wearing my outfit with matching hat and heels , I got a thumbs up and a hug from the nurses .

[docrobbysherry]

The unique, throw back, often home made, Easter style hats r what I find so inspiring!:daydreaming:

320720

[darla_g]

It's all about the Hats!

I could care less about the horses or some race.

Nice hat Sherry! that one is terrific
I want one now, maybe something like this
320724

[Jillcder]

Jill, my wife loves Derby Day as a reason to wear a hat. Sadly I wear dresses more often than she does.

I understand alwayshave I also wear dresses more and own more dresses and skirts than my lovely wife.

[mbmeen12]

I watched first time in over thirty years because of me working weekends. I made my GG look up from her phone to point out the womans hats...sooo colorful.

[Vale]

My wife and I have watched the Derby for the last couple years. I like the dresses & hats, and she likes the horses. Hmmm.. ? vale

[Star01]

Personally I think a dirt track without Sprint Cars is a waste of dirt. I prefer horsepower over horse poop. LOL

[AnnieMac]

I believe the cute little dainty hats clipped high to the side (ala Kate Middleton) are called "Fascinators" for some reason.
For women real and crossdressed both - The Derby is all about the Hat :)

[Barbara Jo]

I watched it also..... all the three and one half hours covered for the only 2 minutes run of the Derby
I am not even into horse racing.... but i did enjoy horseback riding in the past .

So, why did I watch it?
It was a welcomed change for all bad news out there... the pandemic etc.... It was bit of a return to normalcy with a traditional US springtime event .
Yes..... i also loved seeing all the ladies in dresses and great hats which is a tradition at the Derby .:)

[AngelaYVR]

Nowhere near as fancy but I love to get into my hat collection in the spring and summer, such a fun way to keep the sun off you and keep your hair tamed on a breezy day. I would absolutely jump at the chance to attend something like the Derby!

[DanielleDubois]

Down under the big race day is the Melbourne Cup, "The Race that Stops a Nation". It's even a public holiday in the state of Victoria. On the Gold Coast where Danielle lives the race day of the year is the Magic Millions, called that because of the millions of dollars of horse buying that happens the week prior to the big race.

Most of the hats are called fascinators in Australia. There are always some beautiful designs and then there are some absurdly hideous ones that look like the lady lost a bet.:)

I posted a photo thread called "Danielle's Melbourne Cup Fantasy instead of Halloween" on October 30, 2018 where Danielle borrowed a couple of my wife's beach hats and tried to create a derby day look.

[Sabine Janus]

Folks could dress for the derby here and post the pics.

[AllieSF]

I participated in my first ever Kentucky Derby party with my best friend at their island house in a lake in southern Washington. It was also the first time a Derby party was held on the island. About 30 people attended, enjoyed the moment with Mint Julep's and jambalaya. They mixed in well with 2 transitioned women and a super fun NB gender queer friend of ours. I am sure there will be a lot of island talk after the party! I decorated my own hat and came in second place. Not bad for a first timer!

[mbmeen12]

Miss Allie super cute hun....and wonderful idea to have a party.

[Vickie_CDTV]

I have a few fascinators, they are really nice in that they clip on and I don't have to worry about size. I'd love to own a dressy hat that sits on my head directly, but it is impossible to find any dressy ladies hats that fit my big male head.

[Crissy 107]

Allie, Sounds like a fun party and you did a great job with your hat!

[Tanya J]

I watched and thought the exact same thing. The beautiful dresses and hats were outstanding. Surely a few of us in attendance.

[Jillcder]

Love it Allie! You look great and so happy it makes me smile knowing you enjoyed the derby all dolled up.

[AllieSF]

Thanks everyone. It truly was a wonderful experience. For you that do not know, I am a full time trans woman since 2018, and I love every moment of it. I started here as a happy crossdresser, never thinking of transitioning. If any of you want to go out, then find a way to do it. The first time I dressed completely and looked in the mirror at that transformed male face and mind, I knew I had to go out into the real world. I eventually did with two members from this site. You need to be proactive in finding a sidekick, non-sexual relationship, to offer you that initial safe zone, partner in crime, type of moment. Also, try the support groups route. Most are more social groups who give support naturally when meeting up and replying to questions. They can be great fun. Many have special events during the year to dress up a bit more for dining in a safe place like a hotel conference room or out in public somewhere, and maybe even dancing.

All that past experience created my moment this past weekend to be myself dressing over the top on the right occasion for it. I loved everyone there and they appeared to like me too. If they don't like me, that is OK too. They cannot rain on my parade. Don't let anyone rain on yours!

Allie

[Star01]

I have subscriptions to two streaming dirt track channels and watch live live races all weekend. No dresses or hats but racing shirts, hats and blue jeans are the standard garb. My Sprint Car life is overwhelmingly male and I have been known to travel all over the Midwest chasing them. The motel stays have the benefit of getting out from under the wife?s watchful DADT. That has been my go-to travel alibi during the summer for years. I try to extend the stay for an extra night so I can go to races one night and get my girl on the next. No interest in horse racing but I love doing Knoxville, Eldora, and points in between. The Outlaws and All Stars are my passion. When someone mentions Australia I think of WSS and the big races down under. LOL

[Joyce Swindell]

I googled Kentucky Derby dresses 2021
Some pretty outfits! The hats do seem like a must!