Why You Should Try Different Outfits for Cross-Dressing


The very first thing we buy once we find out we like dressing up is to buy feminine clothes.


I’m talking about stuff such as dresses, skirts, and the typical female attire.


These are stereotypical for sure, but they feminize us to a great effect once worn.


But we should be careful not to fall into the monotony of wearing the same outfits over and over again.


Some cross-dressers, especially those who dress up in secret and not so often, tend to keep a small selection of clothes for this purpose.


But this can prove itself to be a mistake since you may become tired of those clothes and lose interest in cross-dressing altogether.


 Why you should try different outfits for cross-dressing


Trying different outfits, on the other hand, may help you keep things interesting.


New combinations allow you to discover new sides of your feminine persona and improve your overall experience.


This way, you add a degree of variance to your hobby and become unlikely to get tired of it.


Besides that, you may be able to express this side of yours more efficiently than you would if you were to limit your options.




With that in mind, my goal here is to make it clear how many benefits you get from trying out new ways to cross-dress.


I’ll also be giving you some tips on how to keep your experience varied and a few outfit suggestions to encourage you even further.


I hope that will help you be yourself for longer.



1. The importance of trying new outfits


 Why you should try different outfits for cross-dressing


We tend to form a certain emotional attachment to our first feminine outfits.


After all, those were the ones who first introduced us to this whole cross-dressing experience.


And it’s ok to keep and even wear them regularly.


However, limiting yourself during your dress-up sessions may cause it to become boring.


And we all know that cross-dressing is meant to be an enjoyable thing.


I mean, what is even the point of doing something you no longer have fun doing?


With that in mind, some of our sisters give up on cross-dressing as they no longer find it to be satisfying.


But that doesn’t solve the problem at all since repressing your true nature only causes more suffering.


 Why you should try different outfits for cross-dressing


One of the explanations for this is that the longer you see yourself in a single outfit, the more flaws you notice about it.


With time, the initial awe you felt during the first time you tried starts to vanish.


You get used to it, and the sight that once caused euphoria now bores you out.


Instead of admiring your feminine self, you start to criticize it, even if there’s nothing wrong with it.


I’ve seen some of your sisters feel that way, even if they passed so well that no one could tell them apart from cisgender women.


It’s more of a psychological burden, as the monotony reduces both our confidence and self-esteem.


 Why you should try different outfits for cross-dressing


But how wearing new outfits can help us out?


Well, once you add a little variance to your cross-dressing wardrobe, you’ll be renewing your looks. It breaks the sensation of monotony and brings back that initial awe.


This is even more effective if you try out outfits of varied styles so you can have a glimpse of how you look in them.


And to add yet another layer of variance, match your style with a makeup design as well.


After all, what matters is to keep exercising your creativity and expressing who you are.


That, without falling into a monotonous routine.


2. Expanding your wardrobe


 Why you should try different outfits for cross-dressing


Purchasing our first clothes is relatively easy to do since the only requirements are that they fit our size and look feminine.


But how do you decide upon what to buy after that?


Well, it’s a matter of understanding your necessities and what would be beneficial for your experience.


For example, if you want more curves, try defined outfits in darker colors to outline your silhouette.


Want to show your cleavage? Try a dress with a bigger opening on the top.


And if your objective is to conceal shapewear, give preference to thicker fabrics.


There are many tutorials on how to choose the just right, but they frequently miss out on an important tip.


And that would be: Avoid buying stuff similar to what you have.


It does nothing else than enforce the feeling of monotony, no matter how many new outfits you buy.


 Why you should try different outfits for cross-dressing


What I want to encourage you to do is take risks with stuff you wouldn’t normally buy.


Experimentation is the key to keeping your cross-dressing experience enjoyable and fresh.


If you use mostly darker outfits, try something with a bit more color, and vice-versa.


Keep not only skirts and dresses but skinny jeans and feminine shorts as well.


Why you should try different outfits for cross-dressing


Make sure you are always trying something new that you haven’t tried before.


And you don’t even have to risk yourself doing so, as the internet allows you to buy stuff almost anonymously.


Besides that, it also helps you find a near-infinite range of outfits, expanding your possibilities.


3. Trying combinations


Why you should try different outfits for cross-dressing


You may also combine different outfits of yours to create something unique.


The bigger and the more varied your wardrobe is, the more combinations you can create.


It is a good exercise of creativity and allows you to create various new looks with little to no cost.


Some shirts are made to be used with a specific skirt or set of clothes.


But nothing may stop you from using it with something completely different.


Who knows how it’s going to look? The trick is to think outside of the books so you can see possibilities no one else thought of before.


Why you should try different outfits for cross-dressing


Another thing I’ve learned in my journey as a gender-fluid cross-dresser is that your hairstyle has a great effect on your overall look.


With that in mind, I recommend you keep at least a few different wigs at your cross-dressing place so as to pair them with different styles of outfits.


And I mean not only the way your hair is styled. But also the color and length of it.


When you think about it, you’ll notice that there are many other possibilities for you to vary your looks by simply changing your hair.


Why you should try different outfits for cross-dressing


4. Maintaining your new purchases


Why you should try different outfits for cross-dressing


Keeping a small selection of outfits still has a certain advantage when compared to the larger ones I’m recommending.


They are easier to hide if you want to keep your cross-dressing a secret.


But I still want to encourage you to keep on expanding your wardrobe, or so to speak.


You may try getting rid of your old clothes so that you can arrange more space for the new stuff.


I recommend you do so every time you feel like you’re tired of a certain outfit and that it has become something monotonous to wear.


But, of course, it works best for those who didn’t form any kind of emotional attachment to their previous outfit.


The problem is that it happens quite often.


Why you should try different outfits for cross-dressing


With that in mind, if you feel like you don’t want to get rid of them, you must figure out where to hide your new stuff.


It may be in the same place you hide your previous stuff, at least until there’s not enough room anymore.


To expand your hiding spot, consider leaving a backpack with your new clothes in a spot no one else but you would bother to check.


That may be inside your closet, on the trunk of your car, or even in the basement.


Why you should try different outfits for cross-dressing


Open cross-dressers tend to keep them with their male clothes to preserve them, but this may not be your case if you’re reading this section.


Clothes that you hide tend to end up wrinkled and require further care.


Make sure you take them to a laundry house at least once a month so they don’t go to waste too soon.


5. Getting inspiration


Why you should try different outfits for cross-dressing


If you feel uninspired, you may struggle to come up with a new idea of outfit to break the monotony.


But I happen to have some tips to help you overcome that. First, go for a walk.


Please take a look at the people you come across on the street, and try to notice the clothes they wear.


It tends to be a good source of inspiration for everyday outfits you may try to replicate later.


But for a more artistic approach, look up a few cross-dressing vloggers or female celebrities.


They tend to give lots of fashion tips and inspire you to do something you wouldn’t think of by yourself.


Why you should try different outfits for cross-dressing


As with any other hobby, cross-dressing is meant to be enjoyable.


But if you do the same thing for too long without variation, all of the excitement will be gone.


Whenever something turns into a routine, it loses the thrill and starts to make us bored.


Thinking of that, it would be smart to try out a few different styles and buy some new outfits.


It will help you keep enjoying your experience as a cross-dresser, with a promise of new adventures and experimentation.


Have you ever felt something like that? Leave your experience in the comments, sharing with our sisters how you’ve managed to innovate.






After reading the article, which of these do you think is the major reason for you to vary your outfits?

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