With over 35 years of crossdressing experience under my belt, I decided I am qualified to put together such a list. So, here are the "necessities" that no man's wardrobe can be without if he wishes to successfully emulate a woman.
Waist Cincher: The right waist cincher can mold your body into a feminine figure by pulling in your waist and displacing what it pulled in to your hips and breasts. My waist cincher displaces enough of me into my breast area that I can nearly fill the B cups of my bra and to often forgo breast forms. I prefer an under-bust corset design with metal boning and a lace-up back.
Wig: Style is your choice, but buy the most expensive synthetic wig you can afford. Inexpensive wigs look like wigs, whereas expensive wigs look like real hair. One of the nicest compliments I ever received was when a woman thought my expensive wig was my real hair.
Panty Girdle: A panty girdle serves two purposes: (1) it shapes your lower torso into a more feminine shape and (2) it allows you to hide your male parts. I tried a gaff to achieve the latter, but discovered that it was very uncomfortable. The panty girdle did a much better job of keeping those parts in place and was much more comfortable. By the way, if you favor short skirts (like me), wear a brief panty girdle rather than a long leg panty girdle, so that your girdle is less likely to show.
Beard Cover: I feel so badly when I see a beautiful girl with the telltale signs of a beard because there is an easy fix—a good beard cover. By "good," I mean a cover that is sheer and orange (to counteract the blue color of a beard).
Little Black Dress: Purchase a classic little black dress and it will never go out of style.
Moisturizer: Moisturize every day, even during periods when you are not going out en femme. After many, many years of shunning skin care, using a moisturizer will make a big difference. Your skin will be smoother, suppler, healthier-looking, and your makeup will go on easier and look better.
Boots: Buy a pair of boots for practical reasons (to protect your feet in cold weather) and for style (to look sexy).
Breast Forms: If you are not naturally endowed or if your foundation garments do not displace sufficient flesh to fill the cups of your bra, then use breast forms (unless you are going for the flat-chested waif look). I have two pairs of forms; one is a small pair to fill out a bra when my flesh just fails to do so and the other is a larger pair for when I fake cleavage and need bigger breasts to match. For those of you on a limited budget, do what I did years ago. I first used birdseed in a baggie as it is an inexpensive way to make your own forms. Also, if you have enough flesh to create cleavage with a little help, fill your bra with Styrofoam cutouts, and then pull your flesh over the top of the bra for that extra affect.
Wallet: Buy a woman's wallet.
Watch: Buy a woman's watch in gold or silver.
Camisole: Buy one camisole, or better, buy two—one in black and another in white or beige. I own a half dozen in various colors because they can solve so many personal wardrobe dilemmas.
Outerwear: If you live in a cooler climate, you will need a woman's coat, woman's gloves and perhaps, a woman's hat if you plan on going out en femme during the winter. A man's coat, gloves, and hat will not cut it if you really want to look like a woman.
Hand Cream: A man has man's hands—especially if he does manual labor. So, shave your hands if they have hair and use a hand cream daily to help feminize your hands.
Deodorant: Unless your manly deodorant is unscented, use a woman's deodorant to avoid the manly scent of a man's deodorant.
Makeup Brushes: Buy a GOOD set of makeup brushes and throw away those foam applicators that came with your makeup. The pros only use brushes. To achieve a professional look, you should use brushes, too.
Gold & Silver Jewelry: Buy one gold-colored set of jewelry (earrings, necklace and bracelet) and one silver-colored set to compliment most of your outfits.
Credit Cards: Most credit card companies will issue additional cards under the same account for other family members. So get an additional card issued to yourself, but just use the initial of your first name with your last name. For example, John Smith would get an additional credit card issued for "J Smith." Use this card when shopping en femme; it is just another small touch that will help you pass as a woman.
Makeup Mirror: A makeup mirror can be your best friend. Get one WITH lights that you can switch to produce various lighting effects and a magnifying option. It is so handy when you are doing your eyes.
Eyeglasses: If you wear glasses, next time buy a pair with unisex frames or if you can afford it, buy a second pair with a feminine frame. (With an eyeglass prescription in hand, you can order eyeglasses online and avoid the embarrassment of buying female frames in person). If you need eyeglasses for reading, you can buy inexpensive reading glasses with very feminine frames just about anywhere (the local pharmacy, Dollar Stores, Wal-Mart, etc.) Also, you can buy woman's sunglasses just about anywhere, too.
Makeup: These are the makeup items that I consider necessities: concealer, beard cover, foundation, powder, blush, lipstick, lip-liner, lip-gloss, mascara, eye shadow, eyeliner, and eyebrow color.
Clip-On Earrings: If you don't have pierced ears, you should collect clip-ons. Clip-ons are a rare commodity and I buy them whenever I come across a nice-looking pair for sale.
Wrinkle Remover: If you have wrinkles, use a wrinkle remover. I never paid much attention to those miracle skin care products that are supposed to remove wrinkles. However, one day I received a free sample of a product that was supposed to deal with wrinkles around the eyes. Looking in the mirror at the wrinkles developing around my 60-something-year-old eyes, I decided to try the free sample. After a week or so, I noticed that the wrinkles were less noticeable. After a few weeks, I had to examine my eyes closely to find the wrinkles. As a result, I was sold on the product and continued using it everyday. Today, the wrinkles around my eyes are still there, but they are not as deep as they once were. As a result, they are less visible especially from afar, which is the goal for using this stuff.
Makeup Boxes: Males need more makeup than real females to look female, so get a big box for your makeup. Don't be shy about buying the biggest box you can find or afford. If the box is not full now, trust me, you will fill it eventually. A big fishing tackle box will do the job.
Jewelry Box: Instead of using traditional jewelry boxes to store your jewelry, use clear plastic stackable compartmentalized storage boxes. They are inexpensive and allow you to see what is stored in the box at a glance.
Tights: Tights are very handy when there is no time to shave your legs and they are also very fashionable right now.
Nails: Long painted nails are so feminine, but how is a guy supposed to hide them when he is in male mode? The solution is to use fake nails. I prefer the pre-painted, pre-glued, press-on nails. They go on in less than five minutes and usually do not come off until you purposely remove them— especially if you clean your nails thoroughly first.
Perfume: Buy one bottle of an expensive perfume and use it when you dress as a woman so that you will have the scent of a woman, too.
Cuticle Remover: Whether you paint your nails or use fake nails, you should use a cuticle remover to clean your natural nails before you go glam.
Razor: Purchase an electric razor with a side burn trimmer and use the trimmer to remove long hair, and then use the head of the razor to remove stubble. For closely shaving your face, get a multi-blade safety razor and always use a new blade before going out en femme in order to get the closest shave.
Attitude: I wish you could buy attitude, but you can't. Attitude is something you acquire and is critical in your success of emulating a woman. When you go out en femme, act as if it is the most natural thing in the world. Don't be ashamed. Rather, strut your stuff. It’s your life and if you want to live it as a woman even momentarily, it’s your right to do so. If someone has a problem, it’s their problem, not yours. Go for it, Girl!