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Finding the right dress is hard for my first time

Started by Samantha80, December 20, 2025, 05:42:47 AM

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Samantha80

I'm having trouble trying to find the right dress for a first buy. I want it to be feminine but not overly sexual, with a nice waist line that I could wear a waist clincher underneath and to have a bit of flair off the hips to give me a nice feminine shape. There is just so much out there I feel overwhelmed and would appreciate any help or advice. Lots of love Samantha x
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Jillian-TG

Don't overthink it and remember if you buy the "wrong" one then it's not the end of the world. You learn from it which will make your next purchase decision more informed.

It will take time to figure out what works for you.

Lori Dee

What I do for almost all clothing.

Use a cloth tape measure and record your measurements. Then go online and look for styles that match what you have in mind. When you find something, check the size. You can buy it online, or note the description of what that style is called. That helps with searching for something similar. Many clothing and department stores have a webpage for shopping. Look to see if they have it. Check the prices. Sometimes it is cheaper to buy online, and you can still pick it up at the store and try it on.
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ChrissyRyan

I suggest going shopping with a woman and have her give you advice and comment of what clothing looks good on YOU.  Make sure she knows that you want her to be quite blunt with you and tell you, no, that one is NOT for you! 

Knowing your measurements is good.  I suggest measuring yourself.  That will help some but gee women's clothing sizes yield different measurements for the same size.  Very weird I know, but true.

Chrissy
Always stay cheerful, be polite, kind, and understanding. Accepting yourself as the woman you are is very liberating.  Never underestimate the appreciation and respect of authenticity.  Help connect a person to someone that may be able to help that person.  Be brave, be strong.  A TRUE friend is a treasure.  Relationships are very important, people are important, and the sooner we all realize that the better off the world will be.  Try a little kindness.  Be generous with your time, energy, wisdom, and resources.   Inconvenience yourself to help someone.   I am a brown eyed, brown haired woman. 

ChrissyRyan

#4
Insofar as MY first dress, I went to a thrift store and picked out a few that I thought were pretty but not super feminine, tried them all on, and bought the one I thought I looked the best in.  Then I wore it around campus later one day that week. I got a nice long walk in, but I did avoid crowds I must admit. 

It was a bit scary but so satisfying too.  That applies to both the purchase and the walk!

This was during my crossdressing years, before I knew I was MTF.


Chrissy
Always stay cheerful, be polite, kind, and understanding. Accepting yourself as the woman you are is very liberating.  Never underestimate the appreciation and respect of authenticity.  Help connect a person to someone that may be able to help that person.  Be brave, be strong.  A TRUE friend is a treasure.  Relationships are very important, people are important, and the sooner we all realize that the better off the world will be.  Try a little kindness.  Be generous with your time, energy, wisdom, and resources.   Inconvenience yourself to help someone.   I am a brown eyed, brown haired woman. 
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ChrissyRyan

I like pintucking, cap sleeves, A-line cuts instead of tight, and pretty colors and prints. 
I enjoy some florals. 
Always stay cheerful, be polite, kind, and understanding. Accepting yourself as the woman you are is very liberating.  Never underestimate the appreciation and respect of authenticity.  Help connect a person to someone that may be able to help that person.  Be brave, be strong.  A TRUE friend is a treasure.  Relationships are very important, people are important, and the sooner we all realize that the better off the world will be.  Try a little kindness.  Be generous with your time, energy, wisdom, and resources.   Inconvenience yourself to help someone.   I am a brown eyed, brown haired woman. 
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Dawn Kellie

My first dress will be from Torrid their Nightfall collection. I'm s bit bigger and have had great luck on sizzling. If I'm not supposed to recommend specific stores I apologize in advance
KELLIE K.
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Petunia

Back in the day when I was a 25-35 y/o CD I used to enjoy shopping time with my wife.

I was her critic/confirmation when she was looking to buy something.

Many a time I sat outside changing rooms when another woman came out with a shop assistant gushing over hoe good something looked amd I'd sit to the side shaking my head.

I'd wait until the other person found something that was flattering a nod.

My wife told them (and me) I was a pretty good eye.

Thing is, you need to have someone unafraid to tell you something doesn't suit even though you love it and may not like why it doesn't suit

Charlotte_Ringwood

Just remember that women's dresses have subtleties that target them to different occasions. You might want to think about where you'll wearing this dress most and then pick something appropriate. It can take time finding your favorites though and your favorites will change as your style grows. It's a fun process of really finding you.

I have a good few dresses yet probably only 1 or 2 for certain occasions. If you're really dedicated there are literally loads of occasion types in women's fashion!
HRT: since April 2025 DIY
GD diagnosis: Dec 2025
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GRS : Jan 2027
Maybe agender, MTF... not sure anymore.
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Charlotte_Ringwood

Quote from: Petunia on January 11, 2026, 06:45:22 AMThing is, you need to have someone unafraid to tell you something doesn't suit even though you love it and may not like why it doesn't suit
I wish I had this but don't know anyone in my life to do this. I tried personal shoppers and they all refused because I'm trans which was quite shocking. I've had to use the wear and see reactions method.
HRT: since April 2025 DIY
GD diagnosis: Dec 2025
FFS: March 2026
GRS : Jan 2027
Maybe agender, MTF... not sure anymore.
My fursona is a kitty called Raveronomy
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