How to Find Clothing As a Cross Dressing Man

Co-authored by wikiHow Staff

Last Updated: October 31, 2022 Approved

Shopping for girls clothes is exciting, fun and quickly can become an expensive hobby. But a basic outfit is easy and you can be out and about in no time, looking good.

Steps

1
Get a measuring tape.
- Measure your chest just under your nipples, add about three inches if you are going to wear a padded bra - this is your bust.
- Measure your waist about an inch above your navel - this is your "natural" girl waist. Also measure your waist a couple of inches below your navel. This is your girl "low waist" - probably also your boy waist.
- Don't worry about hips. Open any website... say JC Penney's and go to the woman sizing chart. Find your dress size. This won't be exact. Waist measurements are the most important as you can always adjust your bust a bit. You will find that depending on the dress style and manufacturer that dress size is not an exact science. Also measure your wrist for bracelet size. Here is the list of what you will need:
- A wig. Don't go to curly or you end up looking like you have a 'Fro. Don't go too long as these wigs are synthetic and beyond shoulder length get pretty tangled and hard to manage. Buy a wig brush too. Try websites like Beauty Trends (Google it) and expect to pay about $50 with discounts. Color? Try a mix... one color with another on the tips or frosting or highlights. Size: they have larger head sizes available and instructions on how to measure yourself for wig size - petite, regular or large. A wig under $30 will probably be cheap nylon and not usable, like Halloween wigs.
- Shoes. Add a size to your mens' size and you have your women's sandal size. Add a size and a half and you have your size in boots and pumps. You may need wide or even extra wide if you are a big girl. Try Payless if you want on the cheap. Large sizes are available at Coward Shoes, onestopplus, silhouettes, and other plus sites. About heels. 4 ¹⁄₂ inch (11.4 cm) heels are great for the photos, but unless you weigh under 120 lbs, they aren't practical. If you are going out and plan to spend some time on your feet, start with 2 to 3 inch (5.1 to 7.6 cm) heels. Black or Black patent are great colors to start with.
- Bra. Buy one. Go with your chest measurement (not bust) and maybe an inch and a half larger. Black is always useful. Cup size? Well - if you are under 160 lbs go with a B or C cup, under 190 pounds a C or D cup. If you are a bigger girl, it is about projection you can probably carry off a D or DD. Breast forms... try PALS on eBay and pay less than $100, or go to a fabric store and buy some weighted forms for under $40 or just use panties until you decide what size you like. Smaller girls can by these everywhere, big girl, try Lane Bryant for larger sizes that don't swallow you up.
- Hose. Hose is makeup for the legs. It forgives nicks from shaving, scrapes from working and other blemishes. Try "sheer to the waist" so you can see your panties. Read the size chart on the back. IT IS BETTER TO GO UP A SIZE. You are probably long in the leg and taller than a lot of girls. You do not want the crotch of the panty hose heading towards your knees. If you try them on and you are baggy all over, ok, go down a size. Put a spare pair in the trunk or your car the first time you go out. Garter belt hose. OK, sounds fun, but reserve it for below the knee skirts/dresses, or rock and roll clubs and hot dates ;> )
- Waist cincher. Unless you are trim and even then... it makes a curve. Rago model 21 is the best. Buy one or two waist sizes smaller than marked.
- Ok, now lets get you decent. Tops and skirts or dresses. Want a young look? Try Alloy website. They even have young fashion for big girls. Skinny and want fetish clothing?, try Lipservice or Hot Topic. Want something more MILT? JC Penneys or Macy's. Upstairs if you are big, try surplice, v neck or wrap around tops. Smaller girls wear higher necklines, boat neck, square neck, draped. Down below, try for a skirt/dress with some flair or something tight. Your hips are small compared to most girls and flared skirts will give you more curve, especially if you define your waist with a contrasting belt or waist tied scarf. Or go the other way if you are thin and wear tight skirts that give you lots of leg. Black is slimming but don't overdo it. A little black dress is great for a starter wardrobe, but add some color with accessories or jewelry.
- Accessories. You need at least one bracelet, one ring and a necklace. Try Emitations for larger sizes - they have clip on earrings too. A purse. Basically, your purse matches your shoes in color, but not necessarily. Black is very practical. For beginners, shoulder strap type will get you over the feeling that you have lost your wallet. Size: small is cute but what are you gonna put in it? Money, lipstick, powder compact, pen, paper all fit in a tiny back, but add a cell phone, camera, cigarettes and you might need more. One inside zipper compartment will keep your ID, credit card, and larger bills from spilling out when you are rummaging around. And remember what you mother told you, "it's not a purse unless you have a tampon in it." The girl in the stall next to you may become BFF's forever.
- Makeup. Too much to say here. Best investment is to go to a MAC store en femme and buy $50 minimum worth (a very small bag) and get a free makeover. They will try to sell you but settle for the foundation, eyeliner pencil, a mascara and one lipstick. Pay attention and ask questions. If a MAC store sounds too scary, try a beauty salon that has a makeup counter or advertises makeup services, call and explain you would like to come at some quiet time. You money will go a bit farther and you may get better attention and training.
2
Shower, shave, get ready and head out on the town. Try to get someone to go with you. If you have a gay bar around, try that as your first outing. They will be friendly and will not bother you as they like men or women without penises. And if you run into your boss or Reverend Tom, well what are they doing in a gay bar? Own your sexuality!

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3
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Community Q&A

Question

Is it gay to cross dress?

Community Answer

It's totally irrelevant. Straight guys like to cross dress and gays like to cross dress, but not all gays like to cross dress. Straight guys like to get in touch with their inner female sometimes and a lot of the clothes feel good.
Question

How do I act when buying women's clothes alone?

Community Answer

Act normally like you would while buying men's clothing. Remember that you're a customer too, and are entitled to buy whatever you'd like.
Question

I am a man I like to wear panties, but I can't find comfortable ones. What one should I buy?

Community Answer

Try bigger panties or a style that is more similar to boxers or briefs, like boy shorts.

Warnings

Keep your knees together and cross your ankles.

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Helpful 57 Not Helpful 15
Dressed as a man, take it home, try it on, and return it.

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Helpful 49 Not Helpful 14
Don't forget makeup removing towelettes, cream/lotion eye makeup remover, and nail polish remover.

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Helpful 49 Not Helpful 19
Be gentle when trying on girls clothes. Tugging can rip seams easily. Take a breath and figure out how things go on.

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Helpful 5 Not Helpful 1
Dress as a girl, you use the ladies room or the ladies changing room. Avoid: children, making eye contact, lingering or behavior that could be construed as peeping. If in doubt, ask the store personnel if there is a unisex facility available

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