8 Must-Dos for the Beginner Crossdresser

I. Intro

Dipping your toes into discovering your femme side begins differently for all of us. Beginning this journey is challenging and is often accompanied by feelings of apprehension and caution.  Some of us start out feeling that our curiosity about looking and acting feminine is somehow wrong or naughty. Because of this, the mere act of seeking support or advice can be overwhelming. Many crossdressers end up making some ill-advised choices simply out of a lack of knowledge or preparation. Over time these can compound and leave you in a place that’s very different from where you envisioned.

We’re here to help you begin your exploration of your feminine side. With the right supplies, attitude, skills, and community you can be sure of some stunning results. There’s nothing wrong with being curious about this, so let’s discuss how to prepare yourself to embark on this journey of self-exploration.

II. In depth

a. Accept yourself

Gender, like many parts of our own identities, isn’t black and white. Often times torturing ourselves about a feeling we have inside that we perceive as wrong can cause more anguish than anything else. Believe me when I say that this anguish and mental tumult is more destructive than any consequence that exploring your inner self could have. 

Accepting this and taking your first steps can be difficult. An important thing to remember is that your journey can end wherever you’d like it to, and every crossdresser has different comfort levels. It’s fine to keep your hobby a secret, to share it with a partner or to be out, loud and proud.

b. Do some research

Being prepared is always a good first step when embarking on a new adventure. After all, if you were going on vacation, you’d read up on where to go and what there is to do when you arrive. Hardly anyone just shows up at the airport without a ticket and buys a ticket to any random destination. Nowadays, with more progressive attitudes towards gender and crossdressing becoming mainstream, it isn’t hard to locate good information to help you move forward.

Nearly every online retailer catering to the crossdressing community has an information section to help you learn about your new curiousity. If you’re more of a visual learner, a simple YouTube search will yield some good results. For those of us who learn by listening, there are also podcasts that discuss how to achieve femininity through crossdressing; I enjoy listening to “The Fox and The Phoenix” which is available on multiple platforms.

c. Choose your wardrobe

What’s your style? Do you see yourself as a buxom blonde or a more demure girl next door type? Figuring out the femme image you’d like to project is the first step to filling up your girl’s closet as well as inspiring the rest of your look. The world of women’s clothing is vast with so many styles and choices. Different clothing styles will emphasize or deemphasize certain aspect of your figure and help you present the feminine aura you’re hoping for. Nevertheless, there are some essentials every crossdresser should have; find some information about some essentials here. 

Something else to consider here is shapewear. If you see your femme alter ego in figure hugging cocktail dresses or short, tight skirts, you’re going to want to think about how to mold your figure to look your best. No crossdressers wardrobe is complete without something to add some curves to the usual male figure.  

d. Invest in a Wig

A woman’s hair can be their most defining feature. Just look at how often notable celebrities can transform their whole look with a new hairstyle. For this reason, it’s important to have a good quality wig to be the capstone of your transformation. When buying a wig, like many products, you’re paying for quality and spending the extra dollar will have results. A cheap wig will look cheap and unconvincing. They’ll also be made of substandard materials that could be uncomfortable and flimsy. Steer clear of costume shops and big box discount retail.

Investing in a medium or high quality wig is definitely money worth spending. Try searching for wig stores in your area online and I’m sure you’ll be surprised at how prevalent they are. The staff in these shops will likely have met a crossdresser before and won’t bat an eye when you walk through the door. In a safe environment like that, you’ll be free to try different styles and colors until you find the optimal wig for you. If you’re hesitant to go shopping in person, Roanyer has a great selection of wigs for sale in a range of sizes and colors. We also have some guidance about choosing the best wig here. 

e. Watch some make up tutorials

Cosmetics are really an amazing thing. By using the correct combinations of contour, foundation, eye shadow, and lipstick you can completely alter your appearance. An inexperienced crossdresser will make a lot of mistakes trying to learn by trial and error; moreover the whole world of cosmetics can be confusing and bewildering.

YouTube, Reddit, and blogs like ours offer a wealth of information to help you get started. I know plenty of skilled make up artists who are self taught by following step by step video tutorials. Here is a link to a video I found helpful; there are lots more on YouTube!

f. Practice

Depending on where you’re taking your crossdressing, just getting your clothing and make up correct won’t be enough. Feminine deportment is crucial when trying to present as female. Feminine mannerisms can be very hard to master because of the many differences between our innate movements and a woman’s. Even the simplest action, like sitting in a chair, can be challenging for an inexperienced crossdresser.

When I’m dressed up I like to feel womanly through and through; deportment and mannerisms are a large part of that. There are a number of exercises you can do to practice feminine movements. I think it’s important to practice these over and over when dressed so they can become second nature. Once these subtle changes have been engrained in ourselves, we can truly look upon our feminine self proudly and with confidence. 

g. Find-a-good-storage-place

Keeping your stuff stored properly and safely is important. There’s a bunch of reasons for this. If crossdressing is your secret, the most obvious reason is to keep your stash of girly things hidden and out of view. A secure storage location will prevent unwanted discoveries and possible confrontation.

The other reason is that a lot of items we need to dress up need to be cared for in order to be kept in peak condition. Wigs, breast forms, girdles, and some other items need specific storage conditions to last and make your investments worth the money. Generally, you’ll want to keep all of these items in a dark place, where there isn’t anything that will get piled on top of them. There’s not many worse things that can happen to a crossdresser then to open your stash to find your breast forms misshapen and you wig tangled and unusable.

I’d recommend getting a study box, cardboard just won’t do. Furniture shops like IKEA sell lots of storage options, but I think it’s possible to get a durable plastic storage unit or box for much less. Roanyer products also come in packaging suitable for long term storage of your favorite items. I keep my stash tucked away in a corner of my closet on the top shelf away from prying eyes. If you’d like more advice about keeping your crossdressing a secret, read Roanyer’s guidance here.

h. Reach out for support

If you’re comfortable sharing your crossdressing, try seeking out a supportive community in your area or online. There are a wealth of resources online to help you connect with like-minded folks. Most big cities will have a sizeable community of crossdressers; websites like meetup.com can help you find them. There will also be a good chance that there will be a bar or two that cater to clientele who share your interest or some variation of it.

There are also a good selection of professional make over services that can help you achieve a stunning transformation. I’ve taken advantage of these from time to time and I can attest to the results. The make up artists and stylists who run these services are familiar with all manner of crossdressers and generally can accommodate most requests. It’s also a wonderful learning experience if you’re looking to upskill yourself.

III. Summary

As we said earlier, having feminine desires and then starting to act on them can be daunting, but also exciting. Learning more about ourselves is an essential part to finding real happiness and confidence. Once we accept these feminine urges as a part of ourselves, each step forward becomes easier.

I sincerely hope that these tidbits of advice are constructive. Each one of our individual journeys is just that, an individual journey, and they are all different.  It’s important for all of us to support each other and share our experiences in hopes of assisting the next reader. Please share your own pieces of advice or your own experience with how you got started dressing and accepting yourself below.