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Crossdressing 101: Part 2 – Let’s Go Shopping!

Professor Amanda continues her symposium.

By Amanda J.

Last time, we looked at what a crossdresser (CDer) is, briefly considering all of its facets before focussing on the sector of the CDing community for whom nothing less than full transformation into a female will suffice and how we come to terms with having those thoughts.  But whilst it’s all very well to have CDing aspirations, how do we actually turn those into reality?  If you’re looking to put your first outfit together or have restricted your purchases to Amazon and other online retailers but, for one reason or another, want to shop on the high street, this is for you.

Dee recently shared her shopping tips with us and an informative read it was too (see ‘D-I-Y Dee-It-Yourself Shopping’ part 1 & part 2).  She amply demonstrated the simple premise that underlines the shopping experience of any gender non-conforming shopper and that’s that the sales assistants don’t care who you are or who you’re buying for one little bit.  Their only real concern is getting the sale and even if it’s blindingly obvious who you’re shopping for, they’re well aware that giving great service, and possibly a bit of flattery, will not only close the sale but will also mean that you’re probably going to return there for further purchases in the future.  And given that most of us live in places with strict equality laws, they know full well that treating you with any less respect than they would treat anyone else may well end up with them losing their job.

So what are you waiting for?

Probably the same as I was.  You’re terrified about the prospect of shoppinig in person, particularly dressed as a guy because the idea of being dressed outside your house, let alone in a busy shopping centre is a non starter.  You’re waiting to pluck up the courage to go and buy that cute dress in the window of the shop you walk past every day.  You’re wondering why people like Kandi & Dee can seemingly march into shops, charm the sales assistants and be treated like princesses when you just feel sick at even the thought of it.  You almost know that as soon as you start going through the racks, a sales assistant is going to approach you and say ‘is sir looking for a gift for his wife?  And would she be about the same size as sir by any chance?’ with a barely disguised smirk as she says it.  Yes, the truth is that, for us novices, shopping is a terrifying prospect.  But it really needn’t be.

Shopping for the inner woman is like everything else we do, it gets easier the more we do it.  But that’s little consolation when you’ve never done it before.  So if, like me, you’re not yet ready to strut your stuff, full femme, in the female changing rooms and you’ll be doing the shopping in your far less fabulous male guise, the question is where to start?

I’ll only make passing mention of Amazon which is, to be honest, a godsend for CDers who can’t or don’t want to shop in person.  Plenty of choice, widespread implementation of lockers to collect purchases if it’s not safe to have them delivered home and easy returns if they don’t fit or you change your mind.  That said, I could write a thesis on how Amazon is singlehandedly killing the high street and we may well find that it becomes the only option in time.  Certainly, my local high street is feeling the pinch with well known names falling by the wayside on a regular basis.

So let’s move onto good old bricks & mortar while we still can.  Where can the nervous CDer go to build her wardrobe?

A good enough place as any to start are supermarkets.  I live in the UK but I’m sure the situation is the same throughout the English speaking world – almost all the supermarket chains have clothing lines available in their larger stores, some of whom also display their ranges on their websites so you can do the browsing before you go in.  That’s the easy part but you still have to run the gauntlet of finding the garment in your size, taking it to the checkouts and paying for it and who knows what you’ll encounter before you’re back to the safety of your car?  Actually, very little.  The great thing about supermarkets is that shopping is done with either baskets or trolleys/ carts so as soon as you’ve located what you want to buy, it can be put in the trolley/basket and, if you’re feeling really nervous, covered with the rest of your shopping.  That still leaves the checkouts but, these days, most supermarkets have self-checkouts so, unless you need a security tag removed, you’re home and dry.  And does a frazzled supermarket employee really have time to analyse your purchase and your motives for buying it while they remove the security tag?

As an aside, I recently saw a cute black dress in our local supermarket at a price too good to overlook.  Home and dry till I asked the (male) assistant to remove the security tag.  ‘Are you sure it’s your colour?’ he asked, laughing as he said it.  ‘Sadly, you didn’t have it in red’ was my response also laughing.  The world didn’t end! He only asked the question because he was 99.9% certain that it wasn’t for me but if I’d done anything other than go along with the joke, the other 0.1% would all of a sudden have become very significant!

Even before the advent of self-checkouts, I found the idea of carrying purchases to the checkouts in a basket very appealing.  It provides much needed emotional detachment from the purchase – a guy with a dress draped over his arm is an obvious CDer, at least in one’s mind if not borne out by reality, whereas a guy carrying a supermarket basket is, well, a guy doing the shopping.

And, in fact, the psychological crutch that is the basket can help in shops that exclusively sell clothing too.  I know from experience that it’s quite daunting to walk into a shop that caters exclusively for women but go into a shop with ladies’, men’s and children’s departments, pick up a basket on the way in and the whole shopping experience becomes a lot easier and less nerve wracking.  Self-checkouts aren’t as prevalent in this type of store but they do exist in some chains.  Even if you have to take your purchases to a manned till to pay, the sales assistant cannot possibly know the background to your purchases – you may know they’re for you but the reality is that many guys are sent by their wives/girlfriends to pay while they have a last sweep around the store in case they’ve missed anything (quite how they could have missed anything after spending way too long scrutinising every item on every rail I know not but that’s one of the wonders of the gender to which we aspire!).

I’ll also mention another trick I have used.   I still feel slightly uneasy shopping in lingerie departments as a male because I believe that these items are personal to women who should be able to shop for them without any feeling of unease (I’m not saying that all women would feel uneasy seeing a man rummaging through the bras but I want to respect the feelings of anyone who does).  So I went on the website, found the item I wanted, checked that it was in stock at the store I was visiting and then printed the web page and wrote the size I needed on the print.  Then it was just a case of finding an assistant and asking her if she could help me find it, which she gladly did.

Shoes are more of a challenge, though.  It can be difficult to find shoes any bigger than a UK size 9 (US 11 in women’s sizes, EU 43) in retail outlets and shoe shops tend not to display shoes in pairs meaning that the intervention of an assistant is essential.

However, we can return to the supermarkets who tend to be fine for ‘sensible’ shoes, either flat or with a minimal heel but if, like me, you favour a higher heel, their ranges tend to range from sparse to non-existent.  Clothing stores usually have a much better range of more fashionable styles and also display their shoes in pairs so, as with clothing, the items can be put straight in the basket rather than having to be carried to the checkout.  Increasingly, the budget shoe chains are starting to display shoes in pairs which keeps their staff costs to a minimum – just pick up a box with the size you want, check that the contents match what’s described on the box and take your purchases to the checkout to pay.

I’m going to gloss over accessories such as jewellery, handbags/purses etc. as these are traditionally items that guys give to wives or girlfriends as gifts so no one should have any hangups about buying these.  And underwear/ lingerie is no different to other clothing in terms of where it is stocked so should not pose any particular emotional challenge.

And that just leaves the head.  Or to be more precise, hair & makeup.  As with pretty well everything else, makeup is readily available from the larger supermarkets and foundation, lipstick, an eyeliner pencil and eyeshadow should be sufficient to start with.  Even Poundland, which is widespread in the UK (my local town centre has three!), sells cosmetics and accessories to help with application so, again, there’s plenty of scope.

Hair can be challenging but by no means impossible.  My first wig came from a fancy dress party costume shop.  It looked far better on the photo on the packaging than it did on me but these shops have a reasonable range, even if you don’t want a 70s afro style or a hairdo in ‘activist purple’!  Early on, I also discovered another good source of wigs and that’s shops that cater for the black community who are enthusiastic wearers of wigs.  Unlike the party stores, the wigs sold in these shops are often from the same ranges sold by specialist shops for the CDing community but at a fraction of the price.  The only real problem with wigs from either of these outlets is that they tend to be either very long or quite short with little or nothing in between.  Mutton dressed as lamb doesn’t even begin to describe the results of some of my wig purchases.

I would also add here that, whilst I’ve never bought a wig from a specialist ‘bricks & mortar’ supplier, they are almost always quite happy to welcome the trans community (some make specific mention of this on their websites) and, due to the nature of their product, are very discrete.

So that’s broadly it – if you’re nervous about confronting sales assistants when shopping for yourself, it’s completely possible to get everything you need with little or no contact with anyone other than to pay for the items.

Before I finish, here are some recommendations for shops where I’ve found it particularly easy to buy women’s items  in guy mode.  For obvious reasons, these are UK based but I’ll add a short description and hopefully, if you’re elsewhere in the world, you’ll be able to draw parallels with retailers in your area – please share in the comments below if you think it would assist others in your area.

Supermarkets.  All of the major supermarket chains have clothing lines including Sainsbury’s (Tu), Tesco (F&F) and Asda (George).  Larger stores have a good range and both Sainsbury’s and Asda display their ranges online.  Shoe ranges tend to be limited to ‘sensible’ styles.  A decent range of cosmetics also available.  All have self checkouts.

Marks and Spencer.  World famous and needs no introduction.  Mid-priced clothing & shoes in a range of heel heights and particularly good for underwear/lingerie.  Some stores now have self-checkouts.  Click & collect available.

Primark.  Popular because of low prices although the quality isn’t particularly high.  Also sells a wide range of shoes in a range of heel heights, accessories and cosmetics.  No self-checkouts as far as I am aware but checkout staff are always too busy to analyse purchases.

Matalan.  A home & clothing retailer with prices between M&S and Primark with a varied range including shoes in a range of heel heights & accessories.  Some stores now have self-checkouts.  Click & collect available.

Shoe retailers.   Both Deichmann and ShoeZone display shoes in pairs and both have manned tills with no self-checkouts.  However ranges above UK8 (EU42/US11) tend to be very limited.

Boots.  Great for cosmetics but the range is so large that you really need to know exactly what you’re looking for before you go in.  Some stores have self-checkouts

Wigs.  As mentioned in the text, specialist party/fancy dress shops and hair shops catering for the black community are ideal but these tend to be localised and there are no national chains. 

I’ve not mentioned charity shops here.  For the seasoned pro, they can be an absolute goldmine but as it tends to be a case of rummaging to find something you like in a size that fits, novices may prefer the established retailers where the stock is more logically presented and easier to find what you’re looking for.

There’s no doubt that shopping en femme is an amazing experience.  Just go back and read posts by any of the other contributors if you’re in any doubt about that.  But even if you’re not ready to take that step yet, you can still put great outfits together without difficulty. 

And as I draw this to a close, here are five takeaways for you:

1.  Don’t ever feel the need to justify why you, a guy, is buying women’s clothing.  More than anything, it’s none of the sales assistant’s business but the reality is that as soon as you start making excuses, they’ll see right through you!  But that said, have a think about why a guy could be buying women’s clothing – would you have the same hangups buying something as a gift for someone else that you have buying it for yourself?  So when you take that gorgeous dress or those killer heels to the checkout, just imagine that you’re buying them as a gift for the amazing woman in your life, only you have to know who she really is.

2.  Sales assistants are the loveliest people.  I can think of a couple of occasions where they obviously knew who my purchases were for but said nothing and gave me the nicest smile as if to say that they understood.   And there’s a simple reason for that – they’ve seen it all before and are far more interested in making the sale than analysing who it’s really for.  Many can spot a CDer a mile off but the novelty has long since worn off for them.

3.  If you are nervous, stores that cater for both genders and kids are generally less daunting than specialist womenswear shops.  Self-checkouts make the buying process a breeze as do stores that provide baskets for you to put your purchases in before you take them to the checkouts to pay.

4.  As women’s sizing is a bit of a dark art, you’re probably going to get it wrong and either buy stuff that’s got enough room for two or so tight that you’ll only manage to get it halfway on and then wonder whether you’ll ever get it off again.  So check the return policy of the shop before you buy, make sure you leave the labels on until you’re sure you’re going to keep the item and, if possible, pay in cash since, certainly in the UK, many stores ask for a name and address before giving a card refund but don’t for cash refunds.

5. ‘Click & collect’ is ideal for purchases if you feel nervous about marching into women’s clothing stores.  The purchases will usually be packaged up and the assistant who serves you will have no idea what’s inside or whether it’s for you or you’re picking it up for someone else.  For retailers that don’t offer click and collect, see if they offer guaranteed next day delivery on their website.  If you know that the coast will be clear, then it’s worth paying a little bit extra on the delivery charges to enable the delivery to coincide with that time.  And if all else fails, there’s always Amazon!

That’s all for now.  Next time we’ll look at putting your head above the parapet and joining the community.


16 Responses

  1. Amanda,
    A wonderful primer for part-time CDers beginning their journey. This is very helpful.

    I agree with you about the shoes. Being a size 12 US/CDN, I cannot get anything at a brick and mortar store. Sigh.

    Thanks for all you do.

    I love your new “Contributors” photo.


  2. Jocelyn, thank you as always for your support and feedback.

    Shoes are a big problem for us all as, even as a UK 8 (EU42/US11), the ranges are starting to thin out, particularly in the more elegant styles. I guess it’s all driven by demand but that’s little consolation to either us or the female community in general where it’s noticeable that girls and women are getting taller and, I guess, their feet are also changing in proportion.

    Thanks for noticing the profile pic! That was one of those ‘one small step, one giant leap’ acts. I loved the old photo, not least because of the part it played in getting me to where I am today. The small step was sending the pic to Kandi, the giant leap was finally being happy to take ownership of my own image and its creation, not rely on the skills of someone else to hide behind. I loved the old photo but this one is what the world sees when I go out and about.

  3. Amanda,
    I could write a book on shopping adventures , on the whole it has become easier because of the new equality policies . The sad part as you say is the loss of High Street shops and turning to online shopping has created problems with sizing as many items are made in the Far East .

    I found UK charity shops a godsend , that was the first time I made friends with sales staff even if some were volunteers .

    The ploy I used in my early male mode shopping was to say I was shopping for my wife or daughter , I worked out my correct size so I would write them down and tell the SA that these were my wife or daughter’s sizing , obviously I suggested they were birthday or Xmas presents and if items didn’t fit would it be Ok for them to exchange them .

    I found makeup shopping more trial and error until I bit the bullet and asked for a skin colour check in Boots , it was quite a revelation sitting in a booth with customers passing being instructed on the correct way to apply the right colour .
    While many suggest retail shop away from your locality but how many of us have tried that and seen a near neighbour . One occasion I had a basket full of cosmetics when a friend of my son stopped to chat to me , his eyeys kept straying to the items in my basket . On another occasion I had a basket full of sale stockings when BHS closed , a couple of close neighbours stood behind me at the checkout line , we chatted as the line moved but there was no way I could disguise my basket , all I had to cover the stocking were two bras and some matching panties !!

    Personally I never had a single problem when shopping in male mode and I will add it was a great deal of fun but It is very special now to shop as an accepted female .

    Perhaps the bigger problem many of us face is how to succesfully hide your purchases , thank goodness all that is behind me now .

    1. Teresa, thank you for sharing your experiences. I think the important message is that there’s only one person we need to justify our purchases to and that’s ourself. Backstories are a great way of bolstering ourselves when making our early purchases but the mother of one of our staff members worked in Evans (UK shop catering for the larger woman) and said they could always spot the guys who were shopping for themselves which, to all intents and purposes, renders anything we say irrelevant.

      1. Amanda,
        Early on the Evans outlets knew they were catering partly for the crossdressing community because of their larger sizing , for that reason they may have been one of the first retailers to train their staff for that eventuality , in basic terms ” money is money !” .

        I’m not so sure we are the only ones to justify our purchases , once I came out to my wife I felt to be fair to her I would limit my spending , while she wasn’t happy for me to shop in charity shops at least she knew I was spending pennies rather than pounds .

  4. Amanda,
    Good starter list for the novice cder learning to shop.
    One of the important take-aways is ‘that it gets easier with repetition’.
    As an example, I remember how scared I was when I went for my first bra fitting at a Victoria’s Secret store (30 years ago). The hardest thing was getting up the nerve to just walk into the store. But I did it. Told the sales associate what I was looking for, got led to a room and tried on several different bras before finding the one I wanted. Now 30 years later, I have no problem going to a (crowded) VS store and waiting in line for a dressing room (in ‘male’ mode).
    Other things to consider. Sizing in women’s clothing can be inconsistent, even within a brand. I’m a US size 10, but not all size 10 fit. What’s called Medium and what’s called a Large differs by brand. Another thing, women’s torso and generally shorter than a man’s. I look for “TALL” versions and purchase those when I can find them.
    Ah shoes. I only wear women’s shoes, women’s shoes fit my feet much better than men’s shoes. Learning how to shop for shoes is important. The first step is finding your size. Again, I am a lucky size 10, sometimes a size 11. I allocate 3 to 4 hours a month to shoe shopping. I also spend time during the month shoe shopping online. When you walk into a shoe store with high heels on, the staff sees you as a serious shopper and I usually get better service.
    Another thing to think about. Styles come in all the time; the good ones sell out really fast never to be seen again. One of my favorite things is my chetah print sherpa, I saw it, tried it on and bought it. It sold out in two weeks! When I wear it, both men and women ask me where I got it.
    Remember, it gets easier the more you do it.
    Happy shopping.

    1. Cali, thank you for sharing your thoughts and insights which contain some great pieces of advice for novices. What I think comes out loud and clear from your experiences is how arbitrary, the deliniation between male and female clothing really is. If a piece of clothing or footwear is comfortable or we like the style, why shouldn’t we wear it? The sales assistants selling the items to us clearly don’t care so why should we?

      And as you highlight, sizing can be challenging and we’re bound to get it wrong, not least because of the variances between different brands.

  5. 1st of all—the more you do it you will find that you no longer have any fear of shopping-male or female –you don’t even think about it any more. 2 times I purchased a dress as a male and in both instances the the clerk said “she will surely love that dress”
    once as a female another customer at checkout remarked that she wished she had some place to buy an evening gown like the one I was buying.
    As to the USA you will be creamed if you buy from a catalog. For years I have hit super bargains at Ross Dress for Less-also at Burlington Coat Factory.No sales help there-same with thrift shops. The key is just to keep stopping in-you will probably find something great every 3 of. 4 times. Many of the bargains I’ve found at these places are in the maxi dress category or evening gowns-because the hems are such that they cannot be shortened thus waiting for a tall person like me

    1. Emily, thank you for taking the time to add your thoughts and for once again underlining that it gets easier the more you do it. There’s a reason why women go shopping so much and if we can get into the mindset that we’re going to have very positive experiences, then the outcome will be a self-fulfilling prophesy.

      And thank you for the advice for those on your side of the Atlantic too!

  6. The only time I shopped as a man was when I started building a wardrobe prior to going out in public for the first time. Many of the larger stores do not have SA’s checking people in & out of fitting rooms so it was easy to pick out a few woman’s items, cover them with a few men’s items and try them on in the men’s fitting room. I never had a problem and it was a good way to find out my proper size in everything from bra’s to dresses.

    The first time I bought lingerie as a man, I stood on a long line holding three bras, some panties, a slip and some pantyhose. Nobody bothered to even look my way and the cashier just rang me up like any other customer.

    1. Fiona, thanks for sharing your experience. I’ve used your trick of hiding a dress under male clothes myself and it’s a great strategy when we’re not used to women’s sizing. And as with everyone else here, you’re living proof that we have nothing to fear!

  7. Hi Amanda,
    Another well thought out, well written post and totally to the point. Personally I think you should take parts one and two and publish ‘A Crossdressers Hand Book’. The information will be an invaluable reference for every cross dresser just starting out never mind saving them a pile of grief. Well done Sis!

    Trish ❤️

    1. Trish, thanks for the compliment! Unfortunately, publishing just parts 1 & 2 would be doing a disservice to parts 3, 4, 5, 6 & 7 which are also in the pipeline!

      There’s a hidden message in all of this, though, which is that we have nothing to fear. I’m sure that most of us, at one time or another, have expended far too much energy worrying about imaginary issues. In the end, we just have to stop thinking in terms of a guy dressed as a woman and instead think of a person dressed as a person. At that point we can start to enjoy this life.

  8. Amanda, appreciate the shout out!

    I believe part of my success is that, however I’m dressed, I’m polite. It’s known as retail hell for a reason; unhappy customers who vent at SA’s for things that aren’t the SA’s fault. I always try to return whatever I try on to where it was hanging, so the staff didn’t have to (I think they appreciate that). I treat them respectfully. Maybe it works, maybe it doesn’t, but I’ve always had good experiences while shopping.

    1. Dee, thank you for the great piece of advice. Ultimately, we should treat others as we would want them to treat us and we ignore that simple rule at our peril.

      I gave you the shout out with good reason. Every week, you demonstrate to us that we have nothing to fear. I’ve often said that I couldn’t do a tenth of the things that you and Kandi get up to but you show all of us that the only barriers to us living the life we want to lead are those we put up ourselves. I certainly wouldn’t be where I am today without that understanding.

  9. I am lucky, I wear a US size 10 for dresses. 10 to 8 in jeans size. I were a size 91/2 US for shoe size. So I can shop at almost any store. I love shopping in person, and I usually tell the sales person it is for me. I bought one dress from Macy’s and the sales lady said that is such a beautiful dress and I told her I am looking forward to wearing it. She did give me a look and then smiled at me. I know of a wonderful wig salon and they treat me as a woman even when I try wigs on as a guy. I have never had trouble buying things, it is nice to know my size, which makes shopping so much easier. I enjoy it more when I shop as Julie, again the sales ladies are always very nice and helpful. It has always been an enjoyable experience. I think it helps when you are comfortable about who you are as a woman.

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