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Shopping for Cross-Dressers

Updated on September 3, 2011

I know most crossdresssers have to be very secretive about their preferences for female clothing. This poses more than just a few problems when it comes to looking for and buying the outfit of your dreams. But there are many ways to get that pretty dress you've been wanting for so long. Many places that are cool about crossdressing and many that exist specially for you.

Specialized stores for crossdressers

These are made for you. They have all the means to enable you to shop discretely for womens clothes and try them on without worrying about getting strange looks. You should be ready to pay a higher price for that extra feature though and there might not be one near where you live even though they're growing in number.

Of course, another great advantage is that you can get the clothes in sizes that you can't find elsewhere. That is especially important when it comes to shoes: If I ever wanted to torture somebody, I’d make them wear high heels that don’t fit for an hour. Check out my separate article on high heels for men.

And you'll find items here that you probably won't find anywhere else such as the sissy dress.

Online shops

The internet has revolutionized the world in more ways than one and crossdressers can get access to cute and beautiful outfits easily and anonymously. Unfortunately its very hard to get the right fit from a Firefox window so I suggest sticking to easy-fit garments. I already mentioned great cross-dresser friendly petticoat stores like dancecenter and setrino (for more on them see my article called men in petticoats). Tights, and underwear as well as most skirts are not a problem when it comes to sizing. Check out my hub on men's panties for more information. But when it comes to tops, trousers and full dresses or costumes it can be a near impossibility to get a perfect fit without trying them on. You should know, even when most women shop for a dress we don’t usually find a perfect fit outright but have to have it adjusted.

That brings me to the next point: Looking around the stores and trying on different outfits is half the fun of it all. Even I love it and you guys are really missing out on something if you only order these things anonymously. There is no substitute for clothes shopping on the high street.

Retail stores in the real world

I realize many crossdressers are concerned about this but I’ll tell you why these are still the best place to go. Firstly, the shopkeepers don’t care who their customers are. In fact, chances are that they get crossdressing male customers regularly (unless its some tiny shop in a remote village) and even if not, you might just get a chuckle and some whispering but I’m sure you can handle that (some guys even like that kind of attention). Hey, you could give them a nice tip. That is likely to endear you with almost ANYONE and it’ll help improve the crossdressers image in society – even if it’s a little artificial. And, every time you go to a regular store, you’re helping society get used to cross dressers a little more. If everyone did that, then you’ll help get a snowball rolling towards a more crossdresser friendly society.

What you can also do, is phone a shop directly and ask them right out if they’re ok with crossdressers. My boyfriend did this after he walked past a tiny dress shop just outside London and was to shy to just walk in. He also told them when he’d be coming around so they were mentally prepared. As a result they were very kind and helpful, They locked the door for him and had him try on the dress and took his measurements to get the size right (actually I still think it wasn’t a perfect fit but that’s beside the point) standing in front of the mirror (it’s a pity I wasn’t there to see it). He enjoyed the experience very much and apparently they said he wasn’t even their first male customer.

So shop workers are not the problem (unless their mean people and then they’re a problem for girls too).

Jewelry shops are a little easier to deal with because traditionally men buy jewels for women and men are wearing jewelry themselves more and more these days.

But another thing that probably worries you is that you might bump into somebody you know while trying on a baby-pink princess outfit. Well you could go to another city where you don’t know anyone. Or if you’re in a big city, you could go to an area where you think its least likely to bump into anyone. Also you could try to find the best time to go to a shop. At prime time, there can be crowds of people all getting impatient with each other. That can work as an advantage as nobody wants to pay much attention to anyone else (such as you) but of course, your friends and colleagues are also more likely to be there at that time.

Bottom line

There are loads of possibilities for crossdressers these days, but most of all I recommend the good old retail stores. Whenever I’m in one, I discretely keep an eye open for men looking around at women’s clothes. I can see it in their eyes when they’re looking for something for themselves. There’s a sort of glow and excitement in their eyes – like a child in a toy store. Its very cute and I see it more often than you might think. Feel free to check out my article on getting feminized.

If you want to buy a ballerina outfit with a tutu skirt, then you might want to get some more information from my article on buying tutu dresses.

Not all elaborate feminine garments are difficult to get in the right size. You might be surprised to read that getting a corset in the right size isn't very hard even for men. Check out my article on male corsets for more on that.

So I hope I’ve inspired you to go and do some clothes shopping of your own. If you know any place you’d recommend please share it with the others in the comments section. But please do not advertise (I will delete those comments) as people want honest recommendations only.

Also see:

Dresses for Men


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    • profile image

      Ryan 5 years ago

      I will wear female clothes when ever I am able. I don't go to specialty stores that cater to cross dressers. I will go and shop for what ever I want whether it be shoes, clothes or intimates. However, there is only one place I shop for intimates which is Victoria's Secret and that's either online or in a local store. For the most part, the people that work at the places I shop don't know that the clothing I buy is for me but I eventually told an employee at Victoria's Secret that the stuff I buy from there is for me because I asked what color of bra would look better on me

    • profile image

      Doug 5 years ago

      I absolutely LOVE shopping!!!!

      My advice is to just not worry about it. Go to stores that are likely to have what you are looking for, don't hesitate to let the salesperson know what you are looking for, and try things on to make sure they fit. Just try not to get carried away and over spend.

      Sales people have been uniformly nice and helpful to me. It is a great confidence booster for those just starting to go out in public.

      One tip: I highly recommend Payless shoes. They carry large size women's shoes and I have been to several in different parts of the US and they are always very helpful.

    • profile image

      rc247 5 years ago

      I know I'm late to this party, but I have to tell you, you are Soooo right! I've made two trips to Lane Bryant and both times I was made to feel very welcome. They didn't even bat an eye when I needed help hooking up a corset I was trying on. It was so exciting and wonderful that I know I'll be going back again!

    • profile image

      annabear 6 years ago

      A couple of years agi, I gathered all of my courage and went into a Torrid in Portland. A sales girl came over to help me and I told her this would sound weird, but I wanted to buy an outfit for myself. She said not all all and proceded to help me find a skirt and top and ushered me to the dressing room. The top was too short(long torso here) so I handed it over the door and she brought me a larger one and also handed me a couple different camisilles to try uner it. The lacey one did really help make the top look better and I told her so. She said "let me see, let me see", so I opened the door and there I stood in the black tights and mary janes I had worn into the store with the short layered black skirt and hot pink top. She said it was awesome and asked if the other sales girl could see, so I stepped out for her. What fun. Ended up buying the outfit, plus two dresses. I gave her a nice tip for being so nice and both sales girls asked me to come back soon. I just haven't been back to Poartland and I bet they have moved on by now.

    • Lucy83 profile image

      Lucy83 6 years ago

      Hi Berta,

      that sounds like the perfect story for my website in the sissy task section ;)

    • Berta CD profile image

      Berta CD 6 years ago from MA - USA

      Hi Lucy,

      Just came across your wonderful article. It's like a breath of fresh air to read supportive articles from real women who appreciate the problems and strange situations that befall us males who are very much in touch with our feminine side yet are unable to enjoy that wonderful part of our life. My knowing wife of 50+ years is tolerating of my Berta side but definitely hates the idea. I love it when I'm out shopping with her and she asks me to join her in the dressing room while she tries her lovely things on. Little does she know that, like a comment above, I'm sitting there with her wishing she was trying dresses and lingerie on me as well!!

      I well remember the time I was still working and stopped by a Sears store on my way home, this was a frequent occurrence back then, and headed for the "Intimates", my favorite place in any store, section. My eyes immediately focused on a 80% off sale rack. On this rack I discovered a lovely floor length white satin nightgown on sale for $8.99 down from the 50 or 60's range. Upon a closer look I noticed the hem was dirt stained. A very nice sales lady came up and asked if she could help. I showed her the dirt and she says that's why it's priced so low but it will wash off. As i was further checking it out I held it up to myself, when I thought she was busy with something else, to get an idea of how it would look and if it would fit. (My wife does this all the time.) Apparently the clerk saw me and asked me quietly, "would you like to try it on?" Already weak in the knees from the feel of this exquisite fabric in my hands and arms I nearly dropped to the floor hearing her question! I think she sensed my nervousness as she continued it's perfectly OK as we have many men who wish to try women's things on. So I let her lead me to a dressing room in the woman's section. I was both nervous and excited at the same time. I slipped off my male things except my satin panties and slid this exquisite garment over my shoulders. Oh how wonderful it felt. There was a knock at the door and the clerk asked if she could see how it was fitting me. OMG what to do, I was so nervous, when she continued "you know all sales are final from that rack and you need to be sure it's the right fit for you. I've helped men, like you, out before and have no problems or hangups with it," so I let her in. Well she told me i looked beautiful and that it fit me perfectly. Then she asked me to turn with my back to her and hold my arms out. Suddenly I felt satin sliding up my arms and saw in the mirror that she was putting a matching satin robe on me. Oh how lovely you look she said. I asked how much for the robe and she pointed out that it was filthy on the back from being dragged on the floor. She explained that when I'd selected the gown she recalled that it was part of a peignoir set and she'd gone and found the robe in the back room. In answer to my how much question she said the whole outfit for the $*.99 sale price! Needless to say I took it, wear it whenever possible and love its fit and feel on my body. Yes, that's the outfit in my photo!!

      Goes to show that sales people will do anything to make the sale no matter how cheap it is!!

    • profile image

      bob 6 years ago

      i like ladey grace and fashion bug thay help find what you are looking foor and let you try them on

    • profile image

      Shirley 6 years ago

      The key is to be respectful. A lot of associates are trained that men who try on are normally flashers. Mall securities are trained this way too.

    • profile image

      Diana 6 years ago

      This is my favorite place

    • profile image

      tom/samantha 6 years ago

      i've just gained the courage to go to a store and get some help. i was thinking nordstrom but was wondering about other cd friendly stores

    • Lucy83 profile image

      Lucy83 7 years ago

      Thanks Kathleen,

      you're right. It is a very special form of romance. I wrote specifically about panties on my site too if you want to take a look. The link is on my profile page.

    • profile image

      Kathleen D.  7 years ago

      My boyfriend and I were shopping together when we ran into a friend of mine. She realized we were shopping for him and he felt very awkward. She reassured him,vowing not to mention it to anyone. She said her ex-boyfriend used to wear panties so it was no big deal to her. She thought of it as kind of a kinky turn-on for both of them rather than anything else. I just think of it as being romantic. Lucy you are doing a great job with these hubs!

    • profile image

      jeannyb 7 years ago

      Lucy your hubs are wonderfully supportive dear , its so refreshing and inspiring to see a beautiful woman with a positive view of men who enjoy their femininity and enjoy expressing it in womens clothing. ty

    • Lucy83 profile image

      Lucy83 7 years ago

      Hi Kathleen,

      it's very much like that with us. So much fun. And you're totally right that they need to come out early in the relationship. I wrote an article on that somewhere.

    • profile image

      Kathleen D. 7 years ago

      I went into Lane Bryant with my boyfriend and they were fine with buying things for a guy to wear. They were happy to make the sale. It probably helped that a real girl was with him in a supportive manner too. I got to go into the dressing room with him to help with the fitting too. More guys should be open about this sort of thing with their girlfriends. Talk about it early in the relationship.

      Both my boyfriend and I are 100% heterosexual, but I thinks it's romantic to get him to wear panties or a bra for me. None of it shows on the outside, and we always shop a good distance from home where no one will recognize us. It's our little romantic secret.

    • profile image

      Suzy 31 7 years ago

      Dear Lucy,

      I have just come upon your hubs today and I must say I can't stop reading them! How refreshing it is to read these comments from a woman's perspective. I refer to myself as transgenndered, but I have a strong male and female side. I am not built like a woman but I like to dress as one. Last summer I was persuaded by an acquaintance to start venturing en femme into straight society, which I did, and I have never looked back. I mostly shop at Nordstrom for cloting and Sephora for makeup. The ladies at both stores know me well and seem to really look forward to me coming in. I am probably much more appreciative of their efforts than most of their female clients and I like to let them know what a wonderful service they are providing. This past Chrstmas I even bought gifts for several of them and they were overwhelmed by the gesture. Shopping en femme has changed my life, and I never knew I could be this happy.

      My advice is to screw up your courage and try the retail stores. As you point out, it's so much more fun and efficient to try on the clothes. It is not an easy thing to do at first but you may just be surprised at how well you are received.

    • Lucy83 profile image

      Lucy83 7 years ago

      Sorry to hear that about your wife Rusty, but if she left you and never mentioned that she had a problem with it, then she's not good enough for you imho.

    • profile image

      Rustyrustynail 7 years ago

      Hi Lucy, I found it quite easy to buy in department stores, and soon got over my shyness. It was harder to go into a small lingerie shop however. Then I started to buy on e-bay. At first it was always the private sales, but now i just buy what I like. My wife sadly did not like it, and eventually left. So now i can get what I want, although I would still trade it all to get her back - she never said a word about my collection till the day she left.

    • Lucy83 profile image

      Lucy83 7 years ago

      Lead by example Stephanie.

      Really, I've seen so many men in women's departments looking at the clothes with a sparkle in their eyes. I never noticed until I became aware of it and now I see it everywhere. It's incredibly cute.

      I hope she gave you good advice.

    • profile image

      Stephanie 7 years ago

      I went shopping today at Macy's for the first time. The saleslady was very nice and helpful. When I told her that I wanted to try on the bra I wanted to buy first, she showed me to the mens dressing room. After that she helped me pick some panties and stockings.

      I then went to Lane Bryant and the saleslady there helped me to pick a brand new skirt and blouse. My very first of my own! she was very polite and helped me find the right size and cordinate the right style and color to look atractive on me. It was a very exciting experience and I am so happy that I did it.

    • Danamarielyn profile image

      Danamarielyn 7 years ago from Midwest

      I think the key is to call ahead, be respectful and friendly. Having done this the experiences have been fine and even though very nervous frequently. Most of the women are friendly, reassuring and try to make you feel comfortable. I prefer smaller shops cause more intimate and fewer people who might gawk.

    • profile image

      tactilicious 8 years ago

      I've found the clerks in hosiery and lingerie departments of major stores like Macy's and Nordstrom's to be very helpful and friendly when approached directly, with no BS. The Nordstrom's hosiery ladies are exceptional, I always ending up having great chats about hosiery and men in hosiery with them, they open up new stock to see if I've seen it, show me hosiery on their legs (I show them mine too) for comparisons, it's a good time!

      Skirts, I just take them to the dressing rooms, usually discussing what I am looking for in the garment with the fitting room clerk. I've had pretty good reaction there, too.

    • profile image

      maggied 8 years ago

      When it comes to buying clothes retail stores definitely offer the best value for cross-dressers. Layne Bryant is one of my favorite stores. I did call ahead before my first visit and was welcomed with open arms. The dressing rooms are private enough to try on clothing and their clerks are more then willing to bring you different sizes on request. I normally just find what I want and walk right over to the dressing room without incident. I was only questioned by a clerk one time as I was about to enter one of their dressing cubicles and the manager quickly came over and apologized.

      I also shop at Macy, Penny's, Dillards and Jone's without incident. I did stop first at their customer service office to inquire about their policy and noone seemed to have an issue with my trying on cloting though they did request that I use the mens dressing room as not to alarm other patrons.

      The important thing I have found is that if you expect to find garment that fit properly then by all means you need to wear the appropriate foundation garments. And if you realistically would like to see the bigger picture then you should wear makeup and your hair or wig in an appropriate style.

    • profile image

      sissyballs 8 years ago

      buying in stores is so much fun. You are right I feel like a kid in a candy store. I love to look at everything for hours and try things on if the salesperson says I may. I know why women love to shop, the clothes are great and so much variety to choose from.

    • Lucy83 profile image

      Lucy83 8 years ago

      Yes thanks for your comment sissychuck. I love the feedback I've been getting from you guys.

    • profile image

      sissychuck44 8 years ago

      Thanks for the great advice and the fact that there are women out there like you who like and appreciate sissies or crossdressers, however you want to put it. i think there are great things from having a girlfriend or wife who appreciates a sissy.


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