Community Conversation => Crossdresser talk => Topic started by: PhilippaRees on March 24, 2026, 06:11:42 AM Return to Full Version

Title: Shopping for Your First Clothes
Post by: PhilippaRees on March 24, 2026, 06:11:42 AM
I was just sitting here with my thoughts about how I bought my first clothes and decided I ought to share them in case they are helpful.
As reported elsewhere it appears that I rather ran at this at full speed but it was a bit more subtle than that.
When I suddenly got the urge to buy a dress I found myself at Walmart within 24 hours. I went later in the evening so it would be as quiet as it could be. I my head I wanted as few people about to clock me looking as possible rather than try and hide in a crowd. I also knew I was definitely going to use the changing rooms and I didn't want to be caught in a line.
I wandered round the department about 10 times trying to get a feel for what was where, American shops really are chaotic, as I still didn't want to be seen browsing even though no one else was there.
Eventually my eye caught a couple of plus size dresses that I liked the look of and some leggings. So I guessed the size I needed grabbed the 2 dresses and some leggings and headed for the changing room. As it happened the leggings were perfect but the dresses were one size to small. So I swapped for the larger size and tried again.
The dress I thought I liked didn't really look right but the other one felt really comfortable on so that was the one I went with.
So with a pair of leggings and a dress I paid at the self service and that was it I had my first female clothes.
I wore both out over then next 2 days and then started doubting myself about whether they suited me or not.
A day day later of found myself in Lane Bryant here is where the psychology kicks in a bit. I was very concerned that I might be seen as a threat to the regular customers so again I went when it was quite. When the assistant
said hello I didn't hesitate I said "I am looking for a dress and need advice, its for me".
She didn't miss a beat and asked "whats the occasion?" I replied "Its for everyday wear".
From that moment on it was a complete blur. She wrote my name on a card and reserved a fitting room. Then we went round the store discussing options and with an armful of dresses I went to the fitting room.
I was happy to walk out to the big mirror and get her advice on every one. We discussed fit, and whether I was comfortable with the look, And all the things I wasn't sure of because I'm not used to them. In particular the low neck line was very scary. She fixed this by finding a cami with lace trim, not that I knew it was called that. It filled the gap just a tiny bit and to my amazement I loved the look.
My next worry was getting cold when I'm out, so we discussed cardigans. The ones on the rail were a bit too plain she said and disappeared out back. She came back with a black one with no buttons and very long at the front. I wasn't entirely convinced but it has become one of my favorite things so she really does have a good eye.
I was there for over 2 hours and I left with a dress, a cami and a cardigan. It was the most amazing experience I've ever had. The ladies in that shop were just wonderful, I never felt more respected or valued in my entire life than I did that day.
And back to the psychology, other customers came and went but I didn't even notice them because I had the protection of the ladies in the shop.
There is more to this story but that is probably enough for now.
Title: Re: Shopping for Your First Clothes
Post by: ChrissyRyan on March 24, 2026, 07:38:01 AM
It sounds as if your ladies clothing store experience was a very good one.  Perhaps you will be returning to the same store and the same salespeople to have another good experience. 

For a while you may be in an accumulation mode, meaning you will be spending more than typical in that time period because you will be establishing your base wardrobe.  After that, you get what catches your eye, new things to replace the old, and maybe somethings you have seen in a magazine or what others wear.  Size changes impact your purchases too, as does the changing seasons and needs for special events and such.

Undergarments, gowns, robes, jackets, shoes, shorts, jeans, hats, purses, the list goes on.  Enjoy your new clothes!


Chrissy


Title: Re: Shopping for Your First Clothes
Post by: PhilippaRees on March 24, 2026, 07:44:43 AM
Hats, I hadn't even thought of that.
Title: Re: Shopping for Your First Clothes
Post by: ChrissyRyan on March 24, 2026, 08:16:27 AM
I do enjoy wearing these clothes I should have been able to just have on everyday of my life. It is a part of each day now going forward and I am happy to do so.  My clothes are much prettier now.  There is so much variety available. 

If you ever shop where you do not have as helpful sales staff, try to shop with one or two women.  They can be a big help to you.  What you think looks good they may advise you to consider something better!  Ask them to be open and honest as can be with their comments.  A local transgender group may have volunteeers willing to shop with you. 


Chrissy
Title: Re: Shopping for Your First Clothes
Post by: Lori Dee on March 24, 2026, 10:01:18 AM
Thanks for sharing, Philippa.

Your experience shows what many members have learned: that our fears are greater than reality. Most people shop in their own bubble and do not pay attention to other shoppers. As an example, think about the last time you went grocery shopping. Can you remember one other shopper there? Usually not because we were in our own bubble too.

Hopefully, your experience will help others who are thinking about going shopping for their first clothes.
Title: Re: Shopping for Your First Clothes
Post by: Dawn Kellie on March 24, 2026, 11:19:10 AM
It should always be this easy.just remember you're the customer.  If they are anything but nice take your money elsewhere.
Title: Re: Shopping for Your First Clothes
Post by: ChrissyRyan on March 24, 2026, 11:21:29 AM
Quote from: Dawn Kellie on March 24, 2026, 11:19:10 AMIt should always be this easy.just remember you're the customer.  If they are anything but nice take your money elsewhere.


That is what I would do also.
Title: Re: Shopping for Your First Clothes
Post by: ChrissyRyan on March 24, 2026, 11:23:46 AM
Shopping online is another way to go but you are likely to have to returns clothes.

Sizing is all over the map.  Material may turn out to be too thin, short or cap sleeves may have too big arm holes, the cut is not comfortable, etc.

Have fun shopping!
Title: Re: Shopping for Your First Clothes
Post by: Dawn Kellie on March 24, 2026, 11:42:09 AM
I've been shoes shopping on line.
Title: Re: Shopping for Your First Clothes
Post by: Charlotte Kitty on March 24, 2026, 11:43:24 AM
I shop 90% online as don't feel too comfortable going into stores particularly if they are busy. Get occasional things if I see them but don't have too many issues with size. Most stuff size 16 uk fits me fine.

Charlotte 😻
Title: Re: Shopping for Your First Clothes
Post by: PhilippaRees on March 25, 2026, 12:19:56 PM
Now I have a bit of time again I can answer some of you properly

Quote from: ChrissyRyan on March 24, 2026, 07:38:01 AMIt sounds as if your ladies clothing store experience was a very good one.  Perhaps you will be returning to the same store and the same salespeople to have another good experience.

I did go back again twice, but I'm back in the UK now so it will be difficult to go again. But I still hope to do so.

Quote from: ChrissyRyan on March 24, 2026, 08:16:27 AMIf you ever shop where you do not have as helpful sales staff, try to shop with one or two women.  They can be a big help to you.  What you think looks good they may advise you to consider something better!  Ask them to be open and honest as can be with their comments.  A local transgender group may have volunteeers willing to shop with you.

I haven't come out to enough women yet but I have a feeling they will be very helpful when I do.

Quote from: Lori Dee on March 24, 2026, 10:01:18 AMHopefully, your experience will help others who are thinking about going shopping for their first clothes.

I really hope so, it was a big reason for posting. But also I just wanted to share my story.

Quote from: Dawn Kellie on March 24, 2026, 11:19:10 AMIt should always be this easy.just remember you're the customer.  If they are anything but nice take your money elsewhere.

Its a good point and very easy to forget when you are nervous

Quote from: Charlotte Kitty on March 24, 2026, 11:43:24 AMI shop 90% online as don't feel too comfortable going into stores particularly if they are busy. Get occasional things if I see them but don't have too many issues with size. Most stuff size 16 uk fits me fine.

I hope my experience gives you a bit of confidence, it was not as bad as my original fear made it out to be.

I was in Tesco at the weekend and saw a very calm man looking through the bra section. No one appeared to notice him. Well no one except me.


Title: Re: Shopping for Your First Clothes
Post by: Stottie Girl on March 25, 2026, 12:41:24 PM
It sounds like you had a very enjoyable time. I think most store assistants will be friendly to you as they want the sales, it's other shoppers where you could possibly get an adverse reaction.

Personally I hate all shops full stop. I avoid them like the plague! It's the noise and the crowds that get me, freaks me out. I did go into a couple of womanswear shops in my twenty's but I felt like every pair of eyes was staring at me though they probably weren't. I grabbed a couple of items I thought might fit (they didn't) paid at the counter and ran away! I'm such a chicken! I didn't feel comfortable at all. I think it would be different if I went dressed. Frankly though I have no desire to go.

Before the internet I did catalogue shopping (remember those!) but since the internet it is so easy to get, try on and return that I don't see the risk. You can order quite a few items in different sizes, pick which one or ones you like and return the rest, no quibble returns are great.

Shoes are where my philosophy falls down. I have bought so many pairs of shoes that don't fit. I hate having size 10's (UK)
Title: Re: Shopping for Your First Clothes
Post by: PhilippaRees on March 25, 2026, 01:01:04 PM
Part 2
A day or so later it dawned on me what a hugely important thing the shop had done for me, well in my eyes anyway, so I went back to thank them for their kindness. I got there slightly later so the morning assistant that helped me before was not there. I had met the afternoon assistant before so she knew what I was talking about when I thanked her and her colleague and agreed to pass on the message.
While I was there she asked if I would like to try on something else, its almost fatal going back because of course the answer is yes.
We looked at a few things and then she suggested a jump suit. I had half looked this one before but wasn't sure. I thought 'well it can't hurt to just try it' so I did.
When I looked in the mirror I thought 'actually I quite like that', then the surprise. As I stepped out of the fitting room I heard across the shop 'OH That's Cute". It was another customer and she was genuinely saying she liked it.
I wore it round the the shop for another 10 or so minutes to get the feel of it.
20 minutes later I walked out with my new jump suit and 8 pairs of panties which I needed anyway.

I couldn't wait to go out in it. At the restaurant later where I wore it, the waiter called me Ma'am. it was the first time I've ever been called that. I was so grateful to him.
Title: Re: Shopping for Your First Clothes
Post by: Lori Dee on March 25, 2026, 01:05:43 PM
Such a wonderful experience, Philippa!

Thank you for sharing.
Title: Re: Shopping for Your First Clothes
Post by: PhilippaRees on March 25, 2026, 01:05:59 PM
Quote from: Stottie Girl on March 25, 2026, 12:41:24 PMIt sounds like you had a very enjoyable time. I think most store assistants will be friendly to you as they want the sales, it's other shoppers where you could possibly get an adverse reaction.

I was very worried about other shoppers so I went at the quietest time I could, the shop was virtually empty. The confidence of the assistants had a big effect on my confidence which then seemed to act like some kind of force field against other shoppers.
Title: Re: Shopping for Your First Clothes
Post by: Northern Star Girl on March 25, 2026, 01:19:46 PM
      @PhilippaRees
Dear Phillappa:

 @ChrissyRyan is very correct.... have one or two supportive and accepting
women friends with you when you shop  for women's clothing. ....
    ....  safety in numbers !
Danielle [Northern Star Girl]


Quote from: ChrissyRyan on March 24, 2026, 08:16:27 AMI do enjoy wearing these clothes I should have been able to just have on everyday of my life. It is a part of each day now going forward and I am happy to do so.  My clothes are much prettier now.  There is so much variety available. 

If you ever shop where you do not have as helpful sales staff, try to shop with one or two women.  They can be a big help to you.  What you think looks good they may advise you to consider something better!  Ask them to be open and honest as can be with their comments.  A local transgender group may have volunteeers willing to shop with you. 


Chrissy
Title: Re: Shopping for Your First Clothes
Post by: PhilippaRees on March 25, 2026, 01:21:52 PM
Actually I forgot to add that I always wanted a jump suit so it was inevitable that I would end up with one. Its another one of those clues that I completely missed.
Title: Re: Shopping for Your First Clothes
Post by: ChrissyRyan on March 25, 2026, 01:33:44 PM
I kind of like the look of some of the bib jumpers/jumpsuits (or overalls too).  They may be a bit inconvenient when going to the restroom though.  Are they?  I have not shopped for these, some may have zippers I suppose or easy ways to open up.

If they were that bib style but like a dress, not as a big of deal for sure.


These bib jumpers are not to be confused with jumpers which are sweaters!
Title: Re: Shopping for Your First Clothes
Post by: PhilippaRees on March 25, 2026, 01:47:32 PM
Quote from: ChrissyRyan on March 25, 2026, 01:33:44 PMI kind of like the look of some of the bib jumpers/jumpsuits (or overalls too).  They may be a bit inconvenient when going to the restroom though.  Are they?  I have not shopped for these, some may have zippers I suppose or easy ways to open up.

Yes they are a bit inconvenient. It was quite a novel experience sitting practically naked in a public restroom for the first time. Nothing, however, could dull my excitement at owning one.

I'm not sure what you mean by bib style. This one is elasticated and you have to step into it from the very top.

I'll try and post a picture of it when I get picture hosting set up
Title: Re: Shopping for Your First Clothes
Post by: ChrissyRyan on March 25, 2026, 02:04:14 PM
Quote from: PhilippaRees on March 25, 2026, 01:47:32 PMYes they are a bit inconvenient. It was quite a novel experience sitting practically naked in a public restroom for the first time. Nothing, however, could dull my excitement at owning one.

I'm not sure what you mean by bib style. This one is elasticated and you have to step into it from the very top.

I'll try and post a picture of it when I get picture hosting set up


Bib style, picture bib overalls.  The two shoulder straps button or fasten in front above the breast line.
Title: Re: Shopping for Your First Clothes
Post by: PhilippaRees on March 25, 2026, 02:14:21 PM
Quote from: ChrissyRyan on March 25, 2026, 02:04:14 PMBib style, picture bib overalls.  The two shoulder straps button or fasten in front above the breast line.

Ahh that makes a lot of sense now that you've described it.

No its definitely not that style.
Title: Re: Shopping for Your First Clothes
Post by: Ciara on March 28, 2026, 10:15:05 AM
What a lovely story Phillipa. Thank you for sharing that.
My first dress purchase was in a store late in the evening also. It was such excitement at the time.
Now I buy my clothes online and collect them at a local store so the don't need to come in the post.
I do love a nice new dress though ❤️.

Ciara
Title: Re: Shopping for Your First Clothes
Post by: Dawn Kellie on March 28, 2026, 01:36:56 PM
Quote from: PhilippaRees on March 25, 2026, 01:47:32 PMYes they are a bit inconvenient. It was quite a novel experience sitting practically naked in a public restroom for the first time. Nothing, however, could dull my excitement at owning one.

I'm not sure what you mean by bib style. This one is elasticated and you have to step into it from the very top.

I'll try and post a picture of it when I get picture hosting set up
I don't like jumpers or 5he like because I have to strip down to pee
Title: Re: Shopping for Your First Clothes
Post by: Susan marcs on March 30, 2026, 01:42:05 AM
Quote from: ChrissyRyan on March 25, 2026, 01:33:44 PMI kind of like the look of some of the bib jumpers/jumpsuits (or overalls too).  They may be a bit inconvenient when going to the restroom though.  Are they?  I have not shopped for these, some may have zippers I suppose or easy ways to open up.

If they were that bib style but like a dress, not as a big of deal for sure.


These bib jumpers are not to be confused with jumpers which are sweaters!
I find jump suites can be annoying  when go to the toilet because you have drop the hole thing down and if you wear a cardigan over the top you have to take that off as well  .. not that I go to the toilet when I'm out dressed up as it freaks me out if others are in there  so I dont
Title: Re: Shopping for Your First Clothes
Post by: ChrissyRyan on March 31, 2026, 05:40:28 PM
Sometimes I wish I was traditional college age again so I could wear some of the cute clothes without standing out as a silly middle aged woman.  But you are what you are!
Title: Re: Shopping for Your First Clothes
Post by: Dawn Kellie on March 31, 2026, 06:03:02 PM
Quote from: ChrissyRyan on March 31, 2026, 05:40:28 PMSometimes I wish I was traditional college age again so I could wear some of the cute clothes without standing out as a silly middle aged woman.  But you are what you are!

I feel you. At way over 50 I feel I missed something
Title: Re: Shopping for Your First Clothes
Post by: ChrissyRyan on April 02, 2026, 04:51:10 PM
Quote from: ChrissyRyan on March 31, 2026, 05:40:28 PMSometimes I wish I was traditional college age again so I could wear some of the cute clothes without standing out as a silly middle aged woman.  But you are what you are!



Charlotte here can pull that off though.
Title: Re: Shopping for Your First Clothes
Post by: Dawn Kellie on April 03, 2026, 02:54:39 PM
I'd love to be able to pull off micro skirts and sky high heels.
Get my drinks for free.
Yet at 57 those days are gone
Title: Re: Shopping for Your First Clothes
Post by: Stottie Girl on April 03, 2026, 03:01:37 PM
Quote from: Dawn Kellie on April 03, 2026, 02:54:39 PMI'd love to be able to pull off micro skirts and sky high heels.
Get my drinks for free.
Yet at 57 those days are gone
Oi! You're only seven years older than me! I still want free drinks! Not willing to subject anyone to me in a micro skirt though, the world is not ready for that abomination!
Title: Re: Shopping for Your First Clothes
Post by: Charlotte Kitty on April 03, 2026, 03:02:54 PM
Quote from: Dawn Kellie on April 03, 2026, 02:54:39 PMI'd love to be able to pull off micro skirts and sky high heels.
Get my drinks for free.
Yet at 57 those days are gone
It's all down to how you carry yourself and how you feel having multiple eyes drilling into you!

I can say it's an adrenaline rush having gone out there in many very extreme outfits!
Title: Re: Shopping for Your First Clothes
Post by: Dawn Kellie on April 03, 2026, 03:13:52 PM
Quote from: Stottie Girl on April 03, 2026, 03:01:37 PMOi! You're only seven years older than me! I still want free drinks! Not willing to subject anyone to me in a micro skirt though, the world is not ready for that abomination!

It's not the years darling it's the miles.😀
Title: Re: Shopping for Your First Clothes
Post by: Stottie Girl on April 03, 2026, 03:26:54 PM
Quote from: Charlotte Kitty on April 03, 2026, 03:02:54 PMIt's all down to how you carry yourself and how you feel having multiple eyes drilling into you!

I can say it's an adrenaline rush having gone out there in many very extreme outfits!
You're just a bairn though Charlotte! You can get away with it!
Title: Re: Shopping for Your First Clothes
Post by: Dawn Kellie on April 03, 2026, 03:28:23 PM
Right now I carry a gut that no one would want to see in a short skirt. It would look like I'm wearing sausage casing.😐�
Title: Re: Shopping for Your First Clothes
Post by: Charlotte Kitty on April 03, 2026, 03:33:43 PM
Quote from: Stottie Girl on April 03, 2026, 03:26:54 PMYou're just a bairn though Charlotte! You can get away with it!

Guess I'm little younger but still 44 is pushing it according to some. I've got tiny hot pants to wear at the furry convention 😺 Anything goes there!