Crossdressing Basic Tips - How to Dress Appropriately

Do You Dress Appropriately?

When you present yourself as a woman, your first impression is EVERYTHING.

What's the first thing people notice? It's not your face, your hair, or your breasts.

It's your CLOTHES.

In fact, clothes are the most important factor in the way people perceive you.

It’s much easier to change your clothes than it is to change your face or the size and shape of your body. But you can't just throw on a dress and expect results.

Wearing women's clothes isn't always that simple. Men’s and transitioning trans bodies are often much different than that of the average woman. We have wider shoulders, longer arms, bigger hands and feet, an Adam's Apple, and sometimes a beer belly. But, there are ways to get around our "flaws" and create an image that we can be proud to present in public.

When many of my friends dress, they are really afraid they will be “read”.

I want to be read and so should you. Why? Because I want other people to read me as the woman I am, not a man in a dress. And to accomplish my goal, it is so important to dress appropriately.

When dressed for public, it is important to think of yourself not as a drag queen, transgendered (although you may be ambigendered), or a crossdresser. You want to be a woman so you should look, act, and think like a woman. You want to be "read" – as female.

You want everyone who observes you, whether from near or from afar, to perceive you as an attractive, well-dressed, well-groomed woman, who is a credit to womanhood. You don't have to be perfect, just presentable.

The most important thing to remember is to wear clothes that flatter your body, clothes that DO NOT call attention to what you want to hide. One of the tricks of a well-dressed woman is that she is always aware of which clothes flatter her figure and which don't. Fashion is all about creating an illusion that is better than reality.

A genetic male, when dressed as a woman, has very special fashion needs. Some of the body challenges one might face include small hips and a flat rear end, a thick waist, broad shoulders, a wide chest and above average height. Let's look at a few ways to solve these problems.

Small Hips and a Flat Butt

I wear a padded undergarment to solve this dilemma. En Femme has a great solution to round out your curves, their Hip and Butt Padded Girdle. For those on a stricter budget, an alternative is to design your own padding using foam rubber you can buy at most any fabric shop. Padding or no padding, remember that light colors make your upper areas look bigger. Wear dark-colored tops and light colors on the bottom to balance out your figure. When wearing a skirt, try an A-line that flares out at the sides, which will make your hips appear bigger. And, buy skirts and dresses with gathers at the waist to create a look of fullness in the hips

A Thick Waist or Beer Belly

Hide your waist by wearing styles with a raised or lowered waistline, such as baby-doll tops or drop-waist dresses. By all means, avoid tucked-in tops. And, don't be afraid to buy clothes in the maternity section if you are having problems finding clothes to fit over your stomach. And, a corset or body shaper will also help.

A Wide Chest

Wear tops and dresses with deep necklines which will create vertical lines and a slimming effect on your torso. Jackets and cardigan sweaters (open or closed) will help break up a broad-looking chest. Remember to wear dark colors as this visually makes your chest look smaller. And, above all, wear proportionate breast forms or enhancers. You don't want your breasts so large that they overemphasize your chest.

Broad Shoulders

Try to avoid wearing tops that cut off at the shoulders (like muscle tees). Instead, opt for short-sleeved sweaters or blouses that fall a few inches from your shoulders. Stay away from puffy or structured sleeves that stand away from your natural shoulder line. If you are wearing a sleeveless or strapless dress, throw on a shawl or a shrug to hide your shoulders. 

Too Tall

Stay away from a monochromatic look (one color or shades of one color) because it will emphasize your height. Choose colors with fullness and gathers to make you look less vertical. Big prints will make you look shorter, as well as contrasting colors on top and bottom, to break up your figure.

Adam's Apple

Unfortunately, all men are burdened with this flaw, even though not all are visible. The best way to overcome the problem is to wear a high-collared blouse, a turtleneck sweater, a scarf, or choker-style jewelry to cover the area. A little bit of base makeup or a touch of bronzer in a darker shade can also minimize the bulge.

Breast Forms and Undergarments

How your outer garments are to drape or hang, how they are going to fit, how they are going to feel and how they will look will depend in a very large measure on what you wear underneath. The right bra and breast forms that are proportionate to your height, weight and figure are essential. The same philosophy goes with your hip pads.

Very few dresses, skirts or blouses in a typical women's department hang correctly on a male body without a layer underneath. "Pull in" or "pad out," whichever you need to do. You don't need to create the "hourglass" curves of a Cinderella, but you want to look balanced on top and on the bottom. If you're 5-foot-3 and are wearing size D forms, cutting back to a C may give you a more proportionate figure. On the other hand, if you are 6 feet tall and wear a B cup, you might want to try going larger. This will depend on your build as well. Think "proportion" at all times.

Lingerie can be important depending on what you are wearing. Your panties will affect your pants silhouette. A soft full or half slip will even out your dress or skirt. Here again, it is not necessary to coordinate between price and value. Hone your shopping skills, but always remember lingerie can be the key. A full slip, in black, white or cream, is one of the most feminine garments any woman can wear. You can even get specialty Pocket bra lingerie, which have pockets to hold your breast forms in place.

Your Body

It is also important for you to study your body and your bodylines. Using a camera on a tripod, photograph yourself from every angle. You should be your own worst critic. Analyze your pictures and determine what improvements, if any, can be made. Identify your body type and decide what works for you and what doesn't. Also, experiment with fabrics and cuts. Not every style will work with every body type. It won't take long to determine what is best for you. If you work at this in an easy, yet systematic way, you will be more knowledgeable and better dressed than most women.

Legs and Feet

Unless nature has blessed you with very attractive legs, you are going to need and want to wear hosiery. Pantyhose are a great choice for everyday, but stockings are much more flattering, feminine and sexy for special occasions. Wearing a corset or a garter belt can maximize the female experience. I love Sheer Elegance stockings, but they maybe out of the affordable price range for many girls. For regular use, any standard brand works very well. Again, there is no correlation between quality and price. Experiment with the brand, the color, the shade and the texture that works best for you. Coordinate your hosiery color with your outfit.


Shoes can make or break an outfit. The biggest question is: "How do my shoes really, truly and objectively look ON ME?" Once again, pictures of your shoes with different outfits will help you decide what looks best for you.

Remember, stiletto heels are not always a necessity with a skirt or a dress. Often, lower heels or even flats will look and work just as well. On the opposite side, heels with jeans can add that little extra to an outfit. It's up to you and how you feel. At times, I can feel just as good in a pair of flats as in 4-inch heels.


Nothing is more important and will have a greater impact on your womanhood. Identify the major department stores, specialty stores or consignment shops that you will feel comfortable frequenting. Develop an "eye" for items that have your name on them. Train yourself to spot a garment or shoes “at 50 feet” that shouts "You!!!"

It’s also fun to shop with a friend or a spouse whenever possible. Not only does it result in a girl’s day out, but also it allows you to "bounce" the item off your companion before purchasing. Just because an item is the latest fad, doesn’t mean that fad is you.

Know Your Environment

What I mean, is when you are dressed, you must know where you are and where you are going. Check out the mall, restaurant, movie theatre, etc…wherever you are going in advance. See what the other girls are wearing so you can get an idea of what you should wear that is appropriate.

Act You Age

Wear clothing that is age appropriate. Simply said, wear an outfit that somebody your age would wear. If you’re 50, would you wear something a teenager would wear? Probably not. On the other hand, if you’re 30 would you wear a granny dress?

Update Your Look

Always be alert for the latest fashions, but remember to use fashion-sense as well. Some clothes stay in style for years, especially the classics like a little black dress or a nice pair of jeans. Some styles recycle every few years. See what the other girls are wearing and find what fits your desires. A Design House like En Femme does a great job at keeping up to date with current fashions and trends and making styles to fit the biological male form – their styles tend to be classically feminine.


Remember these letters and words. Explore, Nurture and Develop. There is not another woman on earth exactly like you. Buy things that work for you and not someone else. All this might take time, but it sure is worth it. Enjoy yourself.


  • Wlliam


  • Elena

    Me too, Patricia. It's the way that nobody pay me attention, because they feel that I'm a ordinary woman and there's nothing to take attraction.
    Appropriate and discreet.
    See you.

  • Elon

    When I go out, I always check out the area I'm in. If i'm in the city I wear dress and heels. But if Im in the burbs I will wear jeans, sweatsuit,sneakers. If I go to A.C. I have a jogging outfit, and jog on the boardwalk. No problems.

  • Patricia Kay

    This is such a great article. It is short but straight to the point and well written.
    I can only speak for myself but I tend to dress much more conservatively and in more of a classic or business appropriate style when I'm going out in public. In public I want to blend in and just be another woman. In private, that may be a totally different matter. In private, or with friends I may dress in a more sexy or provocative style that would be totally inappropriate in public but can be a lot of fun in private or hanging with friends.

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