Makeup is the number one area of interest to crossdresser’s whether they are just starting out or have been at it for a while. I am not a big fan of trying to pass because I don’t think it is achievable for most of us. One thing is for sure though without it you have no chance of passing. After a bit of work I have updated the Crossdresser Makeup page with more detailed instruction and new pictures. I hope the illustrations and procedure make sense to you. I am attempting to give the reader more of a step by step tutorial along with product pictures.
My procedure has sped up my makeup time considerably by simplifying the process. It emphasizes doing the areas that are the most difficult first. The eyes have the most detail with multiple different products and techniques applied in a confined area. Doing them first allows you to make corrections without screwing up your foundation or contouring.
Women’s clothing for crossdressers is not as simple as it may seem there is much to consider depending what your goals are. Are you trying to pass as a woman in public or just blend in without attracting attention? Either way what you should wear depends where you intend to wear it. Summer in Las Vegas or winter in Seattle will be very different in addition to day or evening, casual or formal. Once you have all that sorted out now comes the difficult part which is what looks good on you.
Another school of thought is I don’t care how it looks I just want to wear it. Those in this category buy what they want, wearing it where ever they want, when ever they want. Maybe they are fetish or exhibitionist crossdressers so it is the article of women’s clothing that is important not passing. From my experience it takes them about a half hour to get ready to go out. If I see them coming I cross to the other side of the street and look the other way.
My goal is to look good passable or not and want to achieve it every time I present in public. Most women wear toned down makeup for daytime along with lower heels or flats. Jewelry is minimal and not flashy. Pants are preferred with tank tops weather permitting over dresses and skirts. A long sleeve blouse or light jacket over the top of the tank. Everything in the casual range like most everyone else. The fabrics and colors should be subtle and fit properly. For daywear looking good depends on your choices.
I gave up passing a long time ago and concentrate on blending in to some degree . Maybe trying not standing out so much would be a better choice of words. I am under six feet but over 200 lbs. so I try to look thinner dressing in layers and dark colors. Light blue jeans and white blouse with a dark open jacket is very slimming. The viewers eye will focus on the what blouse and the vertical lines created by the jacket. I have switched to shorter hair teased high on the top making me a little taller but thinner too.
When crossdressed I am always in skirts and sometimes dresses with hose and heels. The skirt is usually a lighter color than the top or jacket. The top is usually solid black with a vertical zipper unzipped to the breast. If I wear a blazer normally it is a one button so the deep Vee accentuates the vertical slenderizing lines.
Dark colors on the upper body make it appear slimmer while lighter colors on the lower body are only for contrast. Crossdressers typically are slender below even after adding hip pads. I always wear heels at night. Normally 3 1/2 inch heels and rarely 4 inch depending on the occasion.
Some crossdressers have broad shoulders (ME) so dark colors on top will make them seem narrower. Horizontal stripes will make my shoulders seem wider so I keep the stripes below the waist. Square neck lines or off the shoulder looks create the same horizontal line problem again. Scoop or Vee neck tops work great along with scarves, anything that creates a vertical line.
Tight is different than fitted which contours the body leaving room where needed. Tight is absolutely form fitting which some call body con because it hugs every curve on the body. I can’t remember ever being able to get away with this look and am too old for it now anyway. If the crossdresser is built slender with little or no muscle definition many can get away even if they are older. Most men are muscular to some degree and if they are well defined this tight look will give you away. People will see muscles first and look closer to see if it is one of those body builder women. Most will see a muscular guy in women’s clothing. Fitted makes more sense unless attention is your goal.
Designers of women’s clothing have a target market they expect to sell to so the colors, cut, patterns and over all style are geared to a certain group. The younger the woman the tighter the look and the more skin shows with the size range being limited to smaller sizes. When the age increases less skin shows, the hemlines drop and the sizes increase along with the prices. I have heard it said that your age plus or minus a decade is a good rule of thumb and I think I follow it at least to some degree. I am over 60 so I might change my mind in a few years.
When you are out in public dressed in women’s clothes people will form an impression of you based on what they observe. If you wish to influence that impression as I do then you will plan what you wear accordingly. In my case the goal is to have women be impressed by my sense of style in the clothing that I choose. To be appreciate my hair and makeup presentation knowing what it takes to get there. Finally to have an overall impression of class and elegance of me. Not saying I get there but that is what I work for none the less. Men notice too but are not interested in me or my presentation which is perfect because I have no interest in them either.
In contrast if I wore blue eyeshadow, bright red lipstick, a red and white tube top with horizontal stripes and a Kardashian style skin tight mini skirt. A pair of platform heels and fingernails that extend an inch beyond my normal nails. Topped off with a long platinum blonde wig cascading down over and beyond my shoulders. My target audience would most likely be repulsed and very likely angry thinking I was mocking them. Men might not be able to resist ridiculing me and feeling they had a license to do so based on my presentation.
I hope this is useful especially to those just venturing out for the first time and they find some women’s clothing they can feel good in.
Hold your head up, point your toes, be safe, and go enjoy yourself in the New Year.
I just returned from a trip to one of my most favorite cities San Francisco with my BFF Ashley. We both crossdressed and met up with two of my Vanity Club crossdresser sisters Kelli and Diane. Diane lives in town but Kelli drove some distance to meet us at our hotel for drinks.
We Uber’d up then we went for dinner at Waterbar Restaurant. Water Bar specializes in seafood and it is the best along with the service. We got an awesome table next to the window with views of the harbor and Bay Bridge. The ambiance is wonderful with large 2 story column aquariums filled with large salt water fish.
This picture with my new short wig was taken in the Warwick Regis Hotel lobby while waiting for the other girls to meet me in the bar for cocktails.
I don’t do crossdressed pictures too often but, this one taken in the hotel lobby with the bar in the background. San Francisco is a special place so I make an exception while there.
I bought the Moto jacket this last summer but had the skirt already and fortunately the zippers matched. San Francisco is the most friendly place to crossdress in my experience anyway. I am crossdressed the entire time that I am there usually and shop to my hearts content.
Shopping while crossdressed is no big deal with Macy’s and the other stores in Union Square. I would recommend wearing flats though because the hills are killer for heels.
For years my wife and others suggested my wearing a short wig for various reasons. I know many CD’s that wear short wigs but never liked them for me.
A few years back I purchased short wig from a wig ostensibly for my wife. The woman dutifully sold me the one I liked in the wrong size and color for me but, then again it was for my wife right? I took it home, tried it on and scared the hell out of myself.
Had I been honest with the sales person and told her I was a CD she might have suggested something else. Maybe she would have told me that a jet black page boy would show every wrinkle in my pale skin. She might have told me it was too small making me look like a gear shift knob.
Do it right
She would have measured my head for the correct size and chosen a color to compliment my skin tone. She might have talked me into a short wig properly sized and shaped for my head. I was too embarrassed to tell her it was for me back then so I did it the hard way. Also the wig was parted down the middle so the hair covered part of my eyes and the curved ends kept falling in my mouth. I tried again some years later with a color that was better but the style looked like a football helmet on me.
Fast forward 30 years and I found one that I liked so I bought another one in a different color. The style is Freedom by Godiva’s Secret Wigs located in Southern California but they have a website. I am now a confirmed CD wearing a short wig all the time.
What I like about the wig besides the cut is it comes in a large size (23 inch diameter) the length I need. The nape down the back is is about 2.5 inches and there is enough hair on top to style it high. Increased height adds length to my face and gives the appearance of narrowing it. The wig is also their own brand and very good quality. It is the only brand that they sell.
I have been wearing high heels for many years and pretty much putting up with the pain. The toes are smashed together in a triangle like the bow of a boat. My toes are bent upward until I walk a few feet barefoot.
A couple of years ago I discovered Vivian Lou Insoles for high heels which, are shown in the picture below.
The clear gel pad going from the arch to just shy of the heel back shifts your weight back. It moves your weight from the ball of your foot to the heel. It more evenly distributes your weight over the whole foot.
Ice them up
Vivian Lou insoles help a great deal but the old ice trick makes high heels even more comfortable. A couple of years ago I wrote about this technique on my other site www.chicladies.org. Recently I made a discovery that makes it even better. I was getting ready to go to a Vanity Club outing in Atalanta and had two new pairs of high heel pumps to wear.
I inserted the zip lock plastic bags with the corner deep into the toe of each shoe pushing it in with my finger. Make sure that the corner is all the way in. Filled the bags about a third of the way full with water and put them in the freezer over night.
I did this three times on one shoe but the other needed a fourth time. I put them on in between to check the fit. When the water froze each night it expanded gently stretching the shoe a little each time. The high heels pictured above are satin but the ones I did multiple times were black kid and black patent leather.
Staying in hotels has its advantages like room and maid service but some drawbacks also. Typically I leave the room in the morning as Duke doing guy stuff returning around 3:00pm to become Micki.
When I leave the room at around 6:00pm as Micki with my heels clicking down the hall hair and makeup perfect I definitely look different. It used to bother me a great deal that the maids would see my wig stands on the dresser which, is the only hint that Duke and Micki are sharing a room. I was worried they might tell other staff and snicker about a crossdresser in the room when they saw me as Duke but not so much any more.
I discovered these hangers on Amazon and tried them out on my last trip.
They go together quickly and disassemble quickly storing flat for shipping.
Maids don’t go into closets or open drawers so the wigs are out of site hanging in the closet. Wives traveling with crossdressers will appreciate the privacy also.
For many crossdresser’s summer means presenting a fuzzier version of your girly self. Most of us opting for pants to cover your legs instead of skirts. For a married crossdresser shaving sometimes it is not optional and it is best to comply. Crossdressers shaved legs might not bother the crossdresser but wives have very valid concerns. Bare legs would be obvious and she would probably decline invitations for BBQ’s and other outdoor activities. That is not fair to her not to mention if kids are involved.
Depending where you live the summer might only last a couple of weeks and then you can go back to your smooth hairless look. Trust me your lady will really appreciate it. Besides most women these days are wearing jeans or some other form of long pants so this is your chance to look CHIC.
In my case she is not the one who decides my stopping shaving my legs and other areas. I am an outdoor person and enjoy outdoor sports and other activities during the summer months. I want to enjoy myself without being concerned about people noticing my crossdresser shaving legs.
Don’t get me wrong I think about crossdressing the whole summer. That is why when the weather cools and the days grow shorter there is a little bounce in my step that turns into a sway once the heels go on. I usually have a little coming out party sort of by taking a trip to San Francisco for a couple of days shopping. Immersion therapy I call it after my summer dry spell.
For those who share my situation cheer up it won’t be too much longer and can still shop online during summer.