Monday, September 7, 2015

How to Get Started Crossdressing

Over the years, so many people have asked me how to get started crossdressing. Well, the truth is that you need to start by getting clothes, though even that can be intimidating and confusing for some people. So, I thought I'd share some basic advice for those people out there looking to get started or looking to step up to the next level.


You can't crossdress without clothes right? That would be cross-nudity and that's something probably better discussed via Tor. The most important thing is get over any fear you may have about getting out and shopping. Will someone see you looking through the women's section? Yes. Will people see you buying women's clothing. Yes. But, you need to realize that most people are so into their own lives that they will not pay any attention to you. Store clerks ring up a hundred people a day and put almost no thought into what people are buying. They're doing a job and they don't care. Store clerks have seen men buying dresses before. Hell, they've seen kids piss on the floor, they've seen crazy people try to steal stuff. They will not judge you. You'll be fine. If you live in a small town and are worried about your uncle or the preacher seeing you, then drive over to the next town or to that bigger town nearby. Or hit the Wal-Mart at 3am. Trust me, a guy buying a bra is probably the most normal thing going on in a Wal-Mart at 3am.

My best advice is to go to Goodwill, Salvation Army or a similar thrift shop. Because you can get clothes on the cheap, you can get a greater variety of looks to try out. If you're uncomfortable taking dresses into the fitting room, thrift shops are cheap enough that an ill-fitting garment won't set you back too much. One rule about fitting rooms though- be sure to use the one of the gender you're presenting as. If you're a beginner, I assume you're shopping in guy-mode, so yes, take the dress into the guy's fitting rooms.

Look around. Pick out three or four dresses, maybe a skirt or two and some tops, depending on your budget. If you don't want to try things on, figure most average guys are probably in the size 10-14 range. Or go for L or XL as well. Sizes vary not only by brand, but sometimes within brand. Even for the exact same dress there can be two slightly different 10s. An important note about ladies' sizing; odd numbers are for juniors and even numbers are for regulars. Unless you're on the smaller size, best to stick with even numbers if you're unsure about your size.

Also check thrift store counters to pick up some inexpensive jewelry. Maybe a necklace, some bracelets and a ring or two.

Cool. Now you're got some outer wear.

Hit up Marshalls, Target, Wal-Mart or a similar store and get yourself a bra and some underwear. You'll probably want a pair of tights too (knowing the average crossdresser). For bras, the number is the circumference of your chest just below where your breast would be and the letter indicates the cup size. You can measure yourself before hand or figure that most guys will be in the 34-38 range. Don't go too crazy on the cup size. Maybe start with a B or C then go from there, unless you have a larger frame in which case a D can can work. Most women are in the B range, so yeah, while large boobs are fun, you don't want to look too ill proportioned. Don't worry about breast forms for now. Just go with some toilet paper and you'll be fine.

Underwear is sized fairly normally, usually in the S, M, L way. These can also correspond to numbers, like 7 being a medium. They usually print both on the label. Pick up what you like and what appeals to you. We can discuss tucking another time, so for now, yeah, pick up what you like.

Tights also have basic sizing an some even have charts with your height and weight on the back telling you exactly what size to get. Now if only they could do that for dresses.

Cool, now you've got all the clothes you'll need for a few outfits! If you want to get more advanced, check out my post on padding, but that's not something you need to do just to start. Just throw on a dress and enjoy it!


For a beginner, just go to Payless. They sell larger sizes and they're not expensive. Plus if you go during one of their sales you can get the second pair half priced. That's great since you'll totally want to pick up a couple pairs. I'd say get a pair of flats and a pair of 2" heels. Shorter heels are better to walk in anyway. You can work your way up to a 6" stiletto. Flats are great to have especially if you're tall. They will also help you blend in since most women rarely if ever wear heels. Try and go for a classic black as that will match with more things.

Payless also sells inexpensive purses. Pick one of those up too if you can.


Hit up Wal-Mart or your local CVS. Try a brand called Wet & Wild, which is inexpensive and not too bad quality wise. You'll want to pick up the following items:
  • Eyeliner pencil in black or brown. Stay away from liquid or gel eyeliners for now.
  • Eye-shadow palette.Try a couple different colors if you can afford it. 
  • Mascara. 
  • Blush.
  • Lip stick. Get a couple different as your pocketbook allows. 
  • Lip liner (get a darker shade). 
  • Foundation. My favorite is Maybelline Dream Matte Mouse. Then I put a powder over top. You'll want to pick up some sponges for application and those will be in the same area.
  • Nail polish. Be sure to also buy nail polish remover! 
Makeup takes a ton of practice. Years of practice. You will not be good at it at the start, but you'll never get good without starting. I also recommend reading Makeup Addiction for tips and tricks once you get past the basic stage.

Have fun playing around! Try different looks, maybe a light basic look or full on crazy whore and everything in between. The more you practice, the better you'll get! So practice!


Unless you have long hair and can pull off that look (maybe you're in a metal band?), you'll want to get a wig. Don't waste your money on cheap wigs. Avoid Halloween or costume shop wigs. You'll want to search for "Beauty Supply" shops in your area. I recommend shopping for a wig in person if you're not familiar with them. Yes, you're going to need to get over any fear your have about sales clerks or people seeing you buying a wig, but plenty of men buy wigs. The stores are going to be used to it. Don't worry! Remember that the heads are displaying the style, but that you can get different colors in that style. Just find a style you like and let the sales clerk know what color you might be looking for.

Most places will let you try on maybe three or four, provided you buy a wig cap for maybe $3 or so. I'd say if you're starting out, try them on and see what works for your face shape.

And I recommend getting bangs or a lace-front if you want it to look natural. You can get a basic lace-front for around $40. If the store offers to cut the lace, let them. They might charge an extra $5 for this service. You can also find YouTube videos about how to cut the lace-front.

For now you can go with just a regular synthetic hair, which is much cheaper than human hair. Try and get a color that matches your regular hair color, but you can also go nuts if you want. I'm not your boss. Have blue if you want! It's your look!


I recommend shaving. It feels so amazing, but I understand that not everyone can though. Shaving your body isn't too much different than shaving your face. But, if you've got some serious hair, I recommend shaving first with electric clippers to thin out the forest. Then rinsing that off. Apply shaving cream (I think Skintimate provides better coverage than regular guy's shaving cream).

My routine is to rinse, shave, then shower and exfoliate with a loufa, then applying basic moisturizing lotion. I'll do my toes, feet, legs, arms, chest and underarms. I shave against the grain.

If you get red bumps on your legs, don't bother with any products that claim to reduce them. They do not work. Red bumps mean you're shaving too close and you can look up YouTube videos on how to shave less close, but mostly it is just practice. I got them for years and now don't ever get bumps.

For my face, I'll shave once with the grain, then a second time against the grain. Then I moisturize.

Always moisturize.

If you can't shave your legs and still want to rock that dress, you are so lucky that thick leggings are in fashion right now! Pick up a pair and have fun!


If you can get away with it, go get your brows waxed! Head on over to the beauty salon or nail place and spend the $8 to get them waxed. Waxing takes maybe ten minutes and is relativity painless compared to plucking or threading (fuck threading!). Make sure the person at the salon knows what you're looking for. Bring a picture if you can. 

Be sure to tip. If she's turned your unruly brow caterpillars into beautiful feminine arched brows, tip that lady a good 100%. She's earned it. 

What to Do Dressed Up?  

Get dressed up! Take a day for yourself. Spend the morning shaving and prepping, then get dressed and do your makeup. Throw on that wig and be amazed at the new awesome amazing lady looking back at your from the mirror.

Take photos to share, maybe take those first steps outside. Try on different outfits to see what works for you. Dressing up is like any skill. It takes practice to get good at it. The more you do it, the better you'll look and feel!

And when you get to the advanced level, go out shopping, try stuff on, then hit the bar for drinks with your girlfriends! Or church if you like. Whatever works for you.

Just enjoy being the beautiful girl your are!


  1. Lovely to come across your site Faith. Lovely to be able to relate to so much of what you write. It is so liberating to meet a fellow traveller.Fancy, I'm not the only one! Who'd have thought?
    Kindest regards,

  2. Just found your fascinating site Faith by clicking on a link on Stana's site. You are a breath of fresh air. At the moment I am still very confused but after many years I have managed to come out to myself which I feel is a major step and after that who knows?

  3. Hi Melissa, thanks for stopping by. Congrats on taking that first step. If it helps, you should know that confusion is the general state of all people in the world, pretty much all the time. :)

    If you get a chance, also check out the sidebar links to my podcast Gender Rebels. We try to go into a lot of depth on the topics covered on this page's how-to guides.

  4. Oh you fill me with such confidence.... thank you :)

  5. Just found your amazing site by clicking on a link posted on Facebook. I finished reading everything on this page and now it got me wanting to start crossdressing.

  6. A really good site and very plainly put. Thanks for this. A mention of make up/eye shadow remover might be a good addition as at first I found this a real problem. V

  7. I must admit the allure of crossdressing lured me in until I saw all the care and money that goes into it. I will have to gradually work my up to it I think but your blog nevertheless inspired and motivated me.