Dressing a Male as a Female

Danielle Jennings
fashionable trans* woman out shopping

In order to be pulled off in an effective and convincing manner, dressing a male as a female requires a great deal of effort. Choosing the right clothing to conceal masculine traits, understanding sizing, and selecting the best foundation garments can help turn an ordinary Joe into an extraordinary JoAnn.

Clothing Tips for Dressing a Male as a Female

Knowing exactly what types of clothing will look best on your frame is key to pulling off a feminine look. Here are a few suggestions:

  • Use caution when wearing strapless or thin-strapped designs. This is because men naturally have broader shoulders than women, and if you want to pull off dressing as a woman seamlessly, opting to show your shoulders is a dead give away that you're a man. If you must wear a strapless style, be sure to have a wrap, stole, or jacket handy to cover up. Also, instead of wearing thin spaghetti straps, choose wider straps that are more flattering.
  • Form-fitting clothing looks better than you think. It may look and feel a little awkward at first, but deciding to wear form-fitting clothing over baggy, relaxed styles is definitely the way to go. It creates the natural outline of a woman's body easier, and helps you create the full illusion. Whether it be dresses, skirts, pants or tops, clothing cut close to the body works best.
  • Embrace darker colors, and be cautious with light or bold ones. Darker colors are going to easily conceal the more masculine elements of your body, thus creating a more convincing illusion. Lighter shades should really be worn with caution because you can't hide anything when the color you're wearing is especially light. Bold colors are more forgiving than light ones, but they also tend to draw a lot of attention, so be aware before you buy.
  • Dress your body as though you were a woman. This bascially means that the way you dress as a man does not apply to the way you dress as a woman. You need to know what female body type you have, and dress it accordingly for the most flattering look. The way to do this is to do a little research on female body shapes and see which one you best fit into, and then style your clothing as such.

Sizing Information

An advantage of online cross-dressing sites is that most of them offer merchandise that is specifically made for men dressing as women, so the fit is exact. However, if you are new to dressing as a female, you may be overwhelmed and not know exactly where to begin with sizes.

When ordering online obviously you can't try things on, but you can have your measurements taken and then you can send them electronically to the seller, who will then help you translate your proper size. If you plan to be in your cross-dressing apparel for extended periods of time you want to purchase foundation garments that are an exact fit to ensure that you're not uncomfortable of tugging at your clothing constantly.

Tips for Lingerie/Foundation Garments

If you are planning to carry out this tricky endeavor, try these important tips to help create a lady-like look:

  • A cross-dressing bra is essential; it provides the foundation of a feminine ensemble. In order to convince the rest of the world that you're a woman, you're going to need an eye-catching bosom.
  • Plan on stuffing this bra with breast form inserts to create a firm and shapely chest. A specialty bra will also provide the contour shaping needed to create the coveted hourglass shape.
  • After the bra is stuffed, it's time to squeeze into a proper fitting pair of underwear. Men will need to conceal their attributes while creating a round and lifted backside.
  • Invest in rear padding to create the illusion of a round and voluptuous booty. Discreet online retailers who specialize in transvestite apparel make specialty panties available, and men can choose from a variety of sexy lingerie options such as thongs, lacy briefs, and boy shorts.

Shopping for Cross Dressing Clothing

An important part of convincingly dressing a male as a female is knowing the best places to shop for cross dressing apparel to create a fitting ensemble. Take a look at some of the places that specialize in cross dressing clothing:

  • CrossDresser - This online site offers casual dresses, full-length gowns, gaff underwear and shoes. It is focused on the glamour and allure of dressing in a female persona.
  • Cross-Dress - From the foundation essentials like breast forms and padded bodysuits to fantasy costumes and lingerie, you are sure to find a host of apparel options to craft a killer look.
  • Crossdresser Closet - When you want to keep things as sexy as possible, this is the place to shop. While you will mostly find items such as extreme lingerie, hosiery, costumes and clubwear, their variety is still enough to make this a worthy shopping destination.
  • Drag-Queen - This site is specifically for drag queens, so you can be certain that everything you need to transform yourself is right at your fingertips. Choose from a wide variety of wigs, evening gowns, shoes and foundation garments.
  • Cross Dress USA - Here, they have more niche items for purchase. Examples include garments made for the leather enthusiast, custom-made gowns and casual dresses, and lingerie that guaranteed to fit like a glove.

The Finished Product

One of the most important elements for men who want to dress as a female is that the finished product is not only convincing, but also beautiful. Selecting the right clothing is essential. While you may not look like a supermodel, you can certainly look like the glamorous twin sister that you never had.

Dressing a Male as a Female