Cross Dresser Shopping

cross dresser shopping miss violet 800-601-6975

So Many Pretty Dresses to Try On!

Crossdressers and Shopping

Shopping is a major aspect of the cross dresser shopping experience.  So many of you have asked me questions about where to shop, how to set it up, who to ask for help, what to expect. And I am always delighted to answer your questions.  One of my cross dressers with vast experience and great success in the shopping arena sent me a fabulous outline of advice.

From a fellow cross dresser to you!


Fran’s Cross Dresser Shopping Advice

You are frustrated with buying womens clothing by mail order.  Trying on your purchase only to be surprised at the drape of the fabric or that the color is not precisely the shade pictured on the web site.  You are weary of purchasing an item in a store, under the pretense that it is for your wife or girlfriend.  Then discovering later that you needed a size 14, not a 12.

Trying on Outfits

You want to shop like a woman.  To experience the thrill of the hunt for that perfect cap-sleeve blouse…the camaraderie you have seen between female sales clerks and their customers.  Even the satisfying exhaustion of a day in which you tried on more outfits than you can count!  Also, you want your clothes to fit.

I have done that kind of shopping, and you can too!

Overcoming Fear

In patronizing at least fifty women’s stores in recent years, I have been uniformly treated with respect and dignity.  I have overcome my fear that sirens would sound if I asked to try on a bra in Victoria’s Secret, heard excellent advice by saleswomen on everything from hem lengths to the tying of scarves.  And, best of all, I have made good decisions about spending my money and building my wardrobe.

For what it is worth, here is what I have learned:

Do NOT call in advance

That would be counter intuitive.  Phoning the store to ask if people there are comfortable with a man shopping for women’s clothes may seem like the sensitive and considerate way to pave the road for a successful outing.  Unfortunately, the first image that is apt to flash into the mind of the clerk or assistant manager who answers your call is that of an extravagant drag queen.  A flashy man in purple hot pants and orange boa sashaying flamboyantly into her shop.  My recommendation is…just go to the store.

Pass on Department Stores

I have found that the women’s wear staffs there are generally more stodgy and definitely chillier to male customers than sales associates in specialty shops.  I am talking about shops such as Cache, Ann Taylor, Bebe’s, and White House/Black Market.  A department store saleswoman is less likely to engage with you on a human level, and when you ask to try something on, the chances are that she will condescendingly point you toward the fitting rooms in the men’s department…two floors up.


Forget trying to pass, unless you are so terrific that even your mother would not recognize you in a cocktail dress.  The trick to a great shopping experience is carrying yourself with both confidence and discretion.  You want to be just another customer.  To blend in.  Women do not dress to the nines to shop anyway.  They spend too much time on their feet, and take off their clothing too often to make heels and back-zippered dresses practical.  If, like me, you are not truly passable, skip the wig and mascara.  Opt for the androgynous look.  Say nicely cut woman’s slacks, a sweater twinset, and flats.  Or go in drab.

Take your time

Women shop carefully, being choosy.  Yes…you are nervous, but resist the urge to grab the first acceptable black skirt, flip out your MasterCard and beat a retreat.  Your goal here is to establish with the staff that you are a serious and discriminating shopper.  That you are comfortable with what you are doing and what you are.  That takes at least ten minutes of perusing all of the various merchandise.  This bears repeating:  Blend in.

Odds are on Your Side

Of the dozens and dozens of occasions when I have shopped for women’s clothing and asked to try something on before buying, I have been turned down just once.  Predictably enough, that was in a department store.  Cross dresser shopping has become a much more “normal” thing.

Connect with a Saleswoman

When one approaches you, and one will because most of them earn commissions on their sales, smile.  Give her your name, and make a point to remember hers.  Tell her what you are looking for.  Seek her counsel.  Establish a bond.  Use her name.  Talk about the clothes.  If you have already identified several things you want to consider purchasing, ask if she will start a fitting room for you.  In shoptalk, that means she will begin to hang those items on the door of a changing room.


Do not be spooked by the idea of trying on an item you might, or might not, purchase.  Half of the adults in the United States sample women’s clothes by putting them on in stores every year.  Most fitting rooms afford all of the privacy you will want.  Virtually every one that I have seen has hooks for your clothes and purse, as well as a full-length mirror and bench or chair.  Louvered doors seem standard too.  I don’t know why.  At some point, the saleswoman will stop by and inquire, through those louvers, “How are you doing?”  That is her way of asking if you need a larger or smaller size.  Or perhaps a different color.  You might even dare to step out for a moment to get her opinion on the outfit you are trying on.

Buy Something

This is an absolute must.  After taking advantage of the saleswoman’s time and generosity, and establishing a connection with her, you must make a purchase.  If you don’t, she and her colleagues are apt to conclude you were only trying on clothes for a cheap thrill.  That will have a negative impact on their reaction to the next cross dresser who comes through their door.  Any purchase  will suffice.  Even if it is just a couple of $10 tailored tee-shirts.  Ideally, of course, you found a little black dress that is just the thing.

Savor the Moment

You have jumped a big hurdle.  Now you understand that you can do it again.  Just last weekend, I made a wonderful 90-minute visit to Talbots store, where a friendly 30-ish saleswoman named Amy was tactfully enthusiastic about helping me.  I ended up buying an ankle-length knit dress, two pairs of shorts, a blue skort, a belt and three tops.  Oh…and a leather handbag.  As I left the store, I knew that my purchases had been wise selections and that they would fit.  I stepped out into the afternoon sunshine with my bulging Talbots bag in my hand, and I felt womanly.


So there you have it my cross dressing friends.  Right from a kindred spirit.  Comments, questions about cross dresser shopping?  Feel free to post them on this blog. 

Considering a shopping session with me?  Read what my customers have to say about their time with me.

Thank you for stopping by!


cross dresser shopping miss violet 800-601-6975

Miss Violet 800-601-6975