Crossdressing Mistakes That You Should Avoid


Crossdressing is a process that takes a long time to perfect, especially for the novice. Being in a hurry to master the art of crossdressing will only lead to mistakes that could end up in failure or ruin the fun of crossdressing for you.


Among many things that people generally get confused about is how to dress appropriately while crossdressing.


Crossdressers wanting to present their female side in a good way typically go out and purchase the first girl clothes they see in the store.


While you are trying to go out and get yourself some pretty women’s clothing, make sure that you avoid making the crossdressing mistakes addressed in this article.


The trick is to match clothing in terms of color, material, and fit.


Crossdressing Mistakes That You Should Avoid


A mistake that you could make is not caring enough about the fit of your new outfits.


When you purchase women’s clothing, you need to ensure that the clothes fit them to complement your new look.


Before buying any woman’s dress, you should try it to avoid ill-fitting clothes, which can ruin your whole plan depending on how revealing or attractive they are.


Before buying a dress, you should first ensure that it fits your body perfectly.


Another common mistake crossdressers make while dressing up as women is trying to wear clothes that are too revealing or attractive for them to wear.


While you want your outfits to be beautiful, you need to ensure they are not too revealing.


Follow the fashion trends when dressing up as a woman.




We have outlined and discussed some of the crossdressing mistakes that crossdressers generally make.


This article should guide crossdressers who do not know how to dress up or what to wear while dressing up as a woman.


Crossdressing does not need any elaborate preparations and can be a fun and exciting adventure for you if you make sure to avoid the common crossdressing mistakes pointed out in this article.



1. Crossdressing Mistakes- Wearing too much makeup


Wearing too much makeup is one of the common crossdressing mistakes that crossdressers make.


While you need to look feminine while dressed in your women’s clothing, you need to apply it in moderation.


Contrary to popular belief, not all women wear makeup every day.


Crossdressing Mistakes That You Should Avoid


Makeup should only compliment your look and never be the main thing on your face.


Therefore, it is advisable to use a light foundation to cover any blemishes or other skin problems before applying your lipstick and eye shadow.


Remember that you are not trying to make a fashion statement; you want to look like a real woman, and you can only achieve this if you take care of the lighting and makeup.




Adding too much makeup can lead to people making fun of you and looking at you differently if they see you in public.


It will also distract your friends and family members from looking at you for the first time.


2. Crossdressing Mistakes- Buying the wrong outfits


This is another common crossdressing mistake that people make while they are out shopping for women’s clothes.


When choosing clothes, you need to be careful not to buy something too revealing or attractive for yourself.


It is said that some male crossdressers throw on some women’s clothes and head onto the streets without considering how embarrassing their outfits look.


Crossdressing Mistakes That You Should Avoid


One of the most common mistakes you should avoid when dressing up as a woman is buying too tight clothes or clinging to your body, which shows off private parts of your body.


You need to make sure that your outfit is pretty and attractive but not too revealing.


Buying the wrong outfits can be embarrassing and can make you look like a clown in public.


When shopping, it is advisable to choose the right outfit that complements your body.


Be cautious of the color, material, and fit of the outfit that you want to buy.


3. Crossdressing Mistakes- Not being careful with heels


Heels are a challenge for not only men but even women.


Avoiding heel blisters and other foot pains is a big question that people have been asking for years.


Experts agree that footwear should be comfortable from the time you wear them from store shelves.


Heels are good for your grace and posture, but they can be challenging to walk in if you do not know how to balance yourself properly when wearing high heels.




It is advisable to practice walking in heels before dressing as a woman to avoid any embarrassing situations.


The first step before wearing heels is to wear socks until your feet are used to them.


Choosing the right heels is also very important.


It would help ensure that the shoes were comfortable and fit your feet correctly before wearing them.


It is advisable to go for round-shaped heels that are not too high to avoid any embarrassing situations when wearing high-heeled shoes.


Crossdressing Mistakes That You Should Avoid


You should avoid putting your foot gently into the heel of your shoe but instead, slide it slowly into place.


You should then tighten the straps around your feet and stand up.


If you feel like your ankles are about to give way, it is advisable to sit down and adjust the straps again until they fit correctly.


Walk around a little bit on your toes before you start walking with heels on the ground.


This will allow your feet to adjust to such high shoes before you try walking long distances or standing still.


4. Crossdressing Mistakes- Not considering the weather


When you are dressing up, it is vital to consider the weather conditions.


Make sure you choose adequate clothes to avoid being too cold or hot while out on the streets.


Make sure always to pay attention to details, like, in this case, the color of clothes that you choose.


Dark colors attract more heat, and you might not feel comfortable wearing them during summer.


Crossdressing Mistakes That You Should Avoid


On the other hand, bright colors attract too much sun and can cause skin irritation on your skin if worn for long hours.


It is advisable to go for lighter-colored clothes for daytime and dark-colored clothes for nighttime.


You should also avoid wearing plastic or vinyl clothing during the summer season, but instead, choose cotton clothes since they are more comfortable to wear in all seasons.


5. Crossdressing Mistakes- Forgetting to shave legs and underarms


As a beginner crossdresser, shaving legs and underarms can be an ordeal.


You should not worry too much because it is possible to shave your legs and underarms the right way if you follow some tips.


To begin with, buy a good shaver with solid blades and change them now and then to prevent any infections caused by unshaven pubic hair.




You should also purchase shaving gel, soap, or cream designed for sensitive skin and use it with lukewarm water to soften the hair before shaving your legs.


This preparation will make the whole shaving process easier and faster.


You can then spread out a towel on the floor or stand in the bathtub for an easy shave.


Crossdressing Mistakes That You Should Avoid


You should make sure that you shave your legs in the opposite direction of hair growth to prevent any cuts and skin irritations after shaving.


It is advisable to apply a small quantity of moisturizing lotion on your legs after shaving them to keep the skin hydrated and smooth.


6. Crossdressing Mistakes- Wearing the wrong underwear for your outfit


It is crucial to consider the underwear you want to wear with your outfit before going out.


When choosing the right underwear, you need to remember that high heels are usually worn with thin panties made of silk.


On the other hand, loose-fitting pants are best matched with thick pantyhose made of cotton blends.


Crossdressing Mistakes That You Should Avoid


It would be best to choose underwear according to what you wear on top since some tops will expose your bra.


Some underwear is meant to be worn over your pantyhose or tights, while some only cover the crotch area.


If you are unsure what underwear to wear with what, it is advisable to wear a thong first and wear whatever looks good on top.




When shopping for underwear, you should first think of the occasion and the outfit you will wear.


You can then choose between new styles or an old favorite.


When selecting vintage lingerie, it is advisable to avoid panties with elastic bands since they stretch over time and might not fit properly after some time.


Make sure that all your underwear fits well enough to avoid any exposure during social occasions.


Crossdressing Mistakes That You Should Avoid


These are some underwear we recommend for crossdressers:

Strapless pantyhose


These are among the most popular choices among crossdressers because they come in various colors and prints.


They can be worn under short skirts or jeans.


Crossdressing Mistakes That You Should Avoid




These are also popular, especially for formal occasions where you need to wear high-heeled shoes.


Some slips are designed to hold breast forms in place and can be worn under dresses.


Slips are sexy, and they can also keep your whole dress in place.


Crossdressing Mistakes That You Should Avoid


Body shapers


These are also good for crossdressers who want to create hourglass curves on their bodies.


They create a shape that is in overall proportion, sexy, and attractive. They can also be worn with most outfits.


Crossdressing Mistakes That You Should Avoid


Lace enhancers for bra and panties


These are great for crossdressers who want to add a feminine touch to their underwear.


They come in a lot of different colors as well as styles and can be worn with most outfits.


Crossdressing Mistakes That You Should Avoid




These are used for securing your male part and keeping it in place.


There are a lot of colors and styles to match your lace or top.


These are also comfortable and can give you the kind of freedom you desire.


In their collection, there is always something to suit your taste and style.


Crossdressing Mistakes That You Should Avoid




These are perfect for crossdressers who want to wear sandals or high heels.


There are a lot of options to give you added confidence for intimate occasions.


Like lace and gaff, options are many as it relates to style, colors, and size.


Crossdressing Mistakes That You Should Avoid


String bikinis


These are another type of thing you can wear underneath short skirts or jeans.


There are colors, sizes, and styles for everyone.


You can either go for a high-waistline string bikini or a low-waistline one.


Crossdressing Mistakes That You Should Avoid


Garter belts


These can be worn with stockings to give a smooth look under short skirts or jeans.


Choose according to your style and color preference, not forgetting size as well.


Crossdressing Mistakes That You Should Avoid


7. Crossdressing Mistakes-Wearing shoes that don’t match your outfit


It’s important to match your shoes to your outfit.


This is because you need to consider the event, where you will be going, and the type of clothing you are wearing.


For example, if you want to wear a long evening gown, high heels or dressy flats will work best.


However, if you are not wearing a gown or going to an event that will allow you to wear flat shoes, it is advisable to choose flats.


Crossdressing Mistakes That You Should Avoid


Choosing shoes that match your outfit does not just have to do with footwear but also accessories such as socks, tights, and pantyhose.


For example, if you wear dark-colored stockings, you should wear shoes with dark colors and avoid wearing brightly colored or patterned pantyhose.


This is because when the socks and the pantyhose are different in color, your legs might look mismatched, and this will not leave a good impression on people who see you wearing them.


You can also combine your outfit and shoes by wearing jewelry such as bracelets, necklaces, and earrings.


Crossdressing Mistakes That You Should Avoid


The above points are the most critical factors you need to consider while choosing and wearing clothing and accessories.


It is really helpful in case you need to put on something new, then go ahead and try it out in front of a mirror to check whether everything fits well together while looking at your reflection.


Don’t forget to take pictures or make videos of yourself while crossdressing so that you can keep the memories and your experimentation process.


If you are unsure about the shoes that will match your outfit, ask for suggestions or advice from someone who knows fashion.


You can also check online for different clothing ideas and tips on buying and where to buy them.


Remember that crossdressing is all about having fun, sharing experiences with others, experimenting with fashion, and feeling comfortable about who you are.


Crossdressing Mistakes That You Should Avoid


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