What was Your Funnest Dress Try on experience ?

I have always wanted the experience of trying on all sorts of dresses from ball gowns to mini dresses . Being able to model them and check myself in the mirror the way women do. But have never really had the guts to approach a store owner or had a woman happily open up her closet to me.

Is the fantasy better than the reality ?

Is the experience even more fun with a gal pal who is happily zipping you in and out of dresses and helping you on your modeling techniques

How about a dress fitting ? Having a lady tell you how cute you look in dresses

The best was a simple day out for shopping and lunch with a nearby friend at a local Boscovs. It was such fun just picking things out and trying them on, and that zipper assistance was a thrill! We got no sideways looks or reactions, so cool.

I had my worst experience in that same store when I did some shopping, left the store and couldn't find my KEYS! I had no one to call and no plan b, thankfully the assistant at the dressing room had found themselves and placed them on the bench, quite an exciting outing!

At the upscale thrift store where my wife and I both shop, I have tried on tops, skirts, pants, and dresses many times. There are changing "booths" with a curtain for privacy, so I never feel like I am invading someone's space. At another thrift store in the area, there's a more shared dressing area, but it also has curtained cubicles, so I was OK being in there, and in fact, once when I was there with a GG friend, two different ladies asked my opinion on what they were trying on. That was a real affirmation!

On the other hand, I once asked a Kohl's saleslady if I could try on a skirt (I was en femme), and she pointed me to the men's dressing rooms on the other side of the store. I was near the women's dressing rooms. I just put the skirt back and left the store. I've been back since, but i haven't tried anything on since then. I would probably try for the women's dressing rooms again, since they also have private cubicles (you can see them from the shopping area).

Probably the part I love the most is when the SA writes my name on the door. They will then come by and ask how you are doing and I always will come out and show them what I am trying on. Many times, they are helpful to the point of getting a different size and often a different garment. Yes, they want to make a sale, but they also are so much better than I at combining parts to make an outfit. I have had them help with zippers, and when trying on wedding dresses, they are sometimes in the dressing room with me getting that huge gown over my head and then doing what ever they do in the back. So many buttons and zippers and laces! I have been out in the common area around the big mirror with other women as we all give comments on what each of us is trying on.

In my experience, dress shops or even the women’s section in a department store, are very safe, inclusive and fun places to be. The reality is so much fun. Do it before all shopping goes online.

Oh, and when a lady tells me that it’s a cute dress…I am in heaven!

I have had some of the best conversations with SA and shop owners. You are not the first guy to walk in and try on dresses. Let them use their knowledge on what looks good on body types and with co,ours…I have so much trouble matching anything.

I have never had assistance but I did get stuck in a dress for several minutes trying to get the zipper unstuck.

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Originally Posted by Christie ann

Probably the part I love the most is when the SA writes my name on the door.

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My favorite is probably due to this fact alone. I wasn't trying on dresses as my partner found a sweater and some pants for me, but the name "Natalie" on the door was so nice to see.

If we are talking specifically about dresses, I am not entirely sure I have a good answer to this. I always find that the idea of going out and trying on clothes is far better than the reality. I used to get a kick out of trying on girl clothes when in boy mode but I don't feel that way anymore. And I am fine with that if I am being honest. I think it shows I have grown beyond the idea that dressing is for thrills and is instead a real part of me. Although, I did spy a couple pretty dresses in Kohl's the other day that I would have loved to wear. But they were a bit ostentatious and I don't want to try them on in boy mode anyway.

It is still fun to find something cute to wear but after trying on 6 or 7 outfits and not really liking any (which is likely more due to my own insecurities and self-criticism) it becomes a bit of a chore.

I have had so many interesting comments from sales associates while trying on dresses a few favorites are, wow that dress looks incredible on you and look at those legs, one associate told while trying on a sleeveless sundress dont worry you have small feminine arms, my all time favorite was an associate at Macys told me she wished her husband would try on some dresses but all he dose is sit on the couch drinking beer watching television wow that one blew my mind.

Not a fantasy - though some stores are more open to providing try on assistance than others

More than just the clothes, I love the experiences, like dress shopping. I wanted the whole bridal experience and I reached out to a bridal store in Las Vegas while I was on a trip there. I set up a fitting, emailing them first explaining I was a crossdresser so they knew what they were getting into. It was so much fun trying in different dresses, seeing what I liked and what I didn?t like. The store owner was very friendly and helpful getting me into a variety of dresses. Not all of them fit perfectly, but that?s true of GG?s wedding dress shopping. I did find The One and ended up buying it.

I came back six months later for a final fitting, this time with my wife and two GG friends as we were in town to see a few shows.

So much fun.

Stuck in dress wrestling with back zipper. Almost a panic. Never more.

Nacysue isnt that the most terrifying. Dancing around in a circle trying to garb back on to a tiny zipper you held just moments ago?knowing you cant reach it. Then the panic sets in.

Many years ago I made reservations at a bridal store to try on bridal dresses. I was assigned a salesperson who helped me try on 4 or 5 different dresses. She was also kind enough to take pictures of me in each of the dresses. One particular dress buttoned in the back. While buttoning it up went OK, when unbuttoning it one of the buttons was too tight and could not be undone. I stood in the middle of the store for over 30 minutes while she tried to get it undone. Finally, she had to cut the button. It was a fun day!Attachment 344809

I have had several fun episodes in the dressing room. As others hear, I love it when they write Abby on the door.

In Freehold, NJ, more than twenty years ago, I was en femme trying on a few sweaters in a dressing room at Macys when several teenage girls took over the room next to mine. The conversation among them went something like this.
Where is Chris?
He is outside waiting for us.
We ought to bring him in here. He would look cute in this dress.
He would look cute. I probably could get him into that dress but not in here. He would never come in the girls dressing room.
Yeah, but I still say he would good in it.
I could do his hair and makeup. He would look cute.
And then they left, chatting and giggling, presumably to find Chris. I still wonder whether he was wearing that dress and maybe all dolled up before the evening was out.

In Colorado Springs, I had two dressing room experiences of note. I was en femme buying a gray skirt suit at Ann Taylor. The SA took me into the dressing room to try on the suit. She had to go back twice to get a better size. She just knocked on the door each time, then walked in with the replacement item. She asked me to step out when I was ready so she could check the fit several times. I got my favorite gray skirt suit that way. She also brought in three camisoles to match, one gray, one maroon, and one teal. And she gave me a discount on the package. The other experience, I was en femme in Coldwater Creek, trying on a midi skirt. I was wearing a jacket that matched the skirt well. When I stepped out to use the three way mirror, a GG my age was there. She complimented me on how well my outfit looked and asked where in the store I found the jacket.

I have also had stuck zipper emergencies. They are the worst, I agree. After several years of building up my courage to go to many places en femme, I actually found the guts to go out of the dressing onto the main floor of a store with the back of a dress unzipped and asked an SA to zip me. I bought that dress, a fave pink lace number.

I had several great experience in several different Dress Barns (RIP). I got Steffi posted on the door, I got zipper help, I got design help, I got check this out help. Once, I had several GG SAs bringing me different sizes and different outfits to try on.

I also met a bunch of girls for dinner in Denver when I was on a business trip. The afterparty was a private group shopping trip with all the girls from dinner at Maurice's.

The reality is not better than the fantasy. But it is good. :)

The first time I ever became brave enough was at the mall in a small store. I was far from home. While browsing around, I asked an employee a question at one point and she answered. Later, I walked up to her again and asked, "Do you allow men to try on clothes?" I guess I assumed that she would be as uncomfortable about the idea as me. But, it was my first time, not hers. She said, "Sure, and looked toward the changing rooms and found an available room. Another employee joined in and they started bringing clothes to me to try on. I was too scared to step out of the dressing room, but I did open the door and get their feedback. It was kind of a non-event, like trying on men's wear. But it was amazing for me.

I did this again and again over the years at various stores. Eventually, I became brave enough to walk out to the 3-way mirror in a dress, etc. Once, a young lady was in the changing area waiting for her friend to come out of a changing room. The sales person was checking on me and I opened the door. The young lady looked on with interest, but not in an entertained way as I had feared.

Eventually, I became brave enough to walk into the store wearing a dress that I had tried on. I was so scared. I was in a dress in front of people for the first time. One couple looked at me, because they walked by where I was in the store. Most people did not notice because they were busy or because the racks were between them and myself.

Only a few times have I had a negative experience, where it was clear that the sales person was not comfortable. Only once was I told that I could not try on clothes. She said that their dressing rooms were only for women. (I was presenting male for all of these.)

I have been complimented while trying on outfits. Sometimes, it was obvious that the outfit was a bad fit for me (figuratively and/or style-wise). In one case, in particular, the sales person said it looked SOOOO good on me. She was lying and trying to make a sale. The best is when the sales person says, "That's not good for you. Let's try something else." That's when you know you have found an honest person. That's a store worth visiting again! :)

Joey

That has to be one of my favourite times. My wife at times will have me try on dresses to see how they look from someone else wearing them. I wrote about New Years and she was trying on my dresses and her dresses and she was giving me the ones she didn't want. We were both trying on dresses and zipping and unzipping each other and making comments on how they look on us. It really is fun almost like two girlfriends trying on clothes together.

I feel like a common theme here is being seen and accepted while trying on clothes. While not specifically “dress” trying on. I have had multiple photo shoot experiences. You would be surprised how much a good makeup artist, hairstylist and photographer can make you look your best.

The whole time they are chatting away with you like you’re one of the girls. They compliment you, assist you with your outfit, help you pick out jewelry, touch up your makeup, help you pose to look your best. It really was some of the most fun I’ve had dressing up. If I had endless money I would hire a full time team to keep me looking pretty.

I am in drab most of the time while shopping. I usually pick out several dresses, skirts and tops and take them into the men's fitting room. When I can get out as Michelle I use the ladies fitting room. I haven't had a bad experience either way and I'm glad to see what fits before I buy instead of having to return something. I agree it would be a dream come true to experience the wedding gown modeling and fitting. An associate wrote my name on the door in Torrid once.

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Originally Posted by Heisthebride

More than just the clothes, I love the experiences, like dress shopping. I wanted the whole bridal experience and I reached out to a bridal store in Las Vegas while I was on a trip there. I set up a fitting, emailing them first explaining I was a crossdresser so they knew what they were getting into. It was so much fun trying in different dresses, seeing what I liked and what I didn?t like. The store owner was very friendly and helpful getting me into a variety of dresses. Not all of them fit perfectly, but that?s true of GG?s wedding dress shopping. I did find The One and ended up buying it.

I came back six months later for a final fitting, this time with my wife and two GG friends as we were in town to see a few shows.

So much fun.

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This would be so much fun to do during Diva Las Vegas.

A few years back I was in Lane Bryant in Edgewater, Md and the sales lady let me try on a dress in the dressing area. While I was trying on the dress the sales lady picked out a few others she thought I would like. As I was in my garter,belt, stockings, panties, waist cincher and bra I discretely stood behind the door and she handed me the dresses. Again she bought me a few more things to try on and again I discretely stood behind the door. As I took the items she smiled and said "You don't need to stand behind the door, I can see you in the mirrors in the dressing room and I love the lovely lingerie you are wearing"

OMG I bet I turned nine shades of red.

I had a great experience at Torrid the manager of the store help me and a friend and of course would have positive comment to sell prodoct lol. Bot it was great cpmimg out looking in that 3 way mirror. did buy one dress. That you for bring back a great memmior for me.

A few years ago I had a gig updating POS hardware (registers, printers, scanners, etc.) in several branches of a women's clothing store. There was an hour or 2 of downtime for me after I'd gotten the hardware installed, while the computers updated their software and configuration. I'd bring in a box or two of my thrift-outlet purchases and use the fitting room area to try them on for real, see what fit, see how they looked in the 3-way mirror, etc. I never tried on any of the merch, just my own things.

Probably the most fun I had dress shopping was a couple years ago. I went to JC Penney in early December. They had a huge selection of dresses for holiday parties and New Years Eve. I must have tried on a dozen dresses, going for the most glamorous and sparkly styles. Having a bestie to share the experience would have been the icing on the cake but I was by myself. There were no SAs around. I did end up helping a GG fellow shopper with a few zippers.

ZIPPER TIP: I have a little helper I keep in my purse when I go shopping; a 3/0 circle fishing hook on a 15 inch length of ribbon. I cut the barb and sharp point off. Hook it on the zipper before stepping into the dress and you can easily operate in the zipper by pulling the ribbon. (I was shopping in a thrift store in male mode once and tried on a dress. Of course, the zipper got stuck and I had to step out into the store in the dress to find help! Vowed that would never happen again!! Probably another memorable dress shopping adventure)

There was a small independent dress store in the next city. I stopped just to browse. The store clerk and I hit it off quite will and when I asked if I could try on a couple of dresses I liked, she said sure and showed me to the dressing room. As I was trying on the dresses, she brought me a couple of more she thought I would like. While I was still in the dressing room, another female shopper walked in started shopping. The clerk walked near the dressing room, gave a quiet knock on the door and whispered through the door, "heads up".

I waited until the other shopper left the store before coming out of the dressing room. The clerk smiled and said I thought you might be embarrassed and did not want to make you or the other shopper uncomfortable. We both had a chuckle and I purchased one of the dresses.

Shortly after that, the store closed.

We were at Macy's and I found a dress I wanted to try on. My wife roamed the racks as I did.
Once I had it on I went to the entrance of the dressing room to see if she was there. I scanned the racks for her. As I did this older woman looked at me and said "He's going to love you in that dress". I smiled broadly and thanked her. Not finding my wife I went and changed and you bet I bought that dress.