How to Take That First Step of Gathering Everything You Need to Crossdress

Now, where to start? In this article, I will be going over the very first steps that I and many others will have taken when adventuring in crossdressing. My first steps will not be the same as yours or anyone else’s, so please take your own pace rather than following this article as a rigid ‘To-Do’ list.

I have decided to organize things neatly across various areas, which, when understood together, will help you achieve your perfect crossdressing look. I would recommend taking the time to go through each step until you’re happy and confident moving on to the next; it’s not a race, and never will be, sis.

Styles

Stepping into crossdressing means you’re now free to look at any fashion trends throughout history and find one that appeals to you. Though there are a lot of crossdressers who will aim for a modern look, nothing is stopping you from stepping into home, 60s polka dot dresses, or 90s pencil skirts! I would even implore you to explore fashion through the ages!

But it is not only fashion that changes, but also the people who follow it. By this, I mean those societal groups that are well-known for expressing their personality. From goths to E-girls, there are so many to choose from. I find myself drawn to the sharper angles of the 2000s.

Bodysuits/Breast Plates

As I am not personally blessed with a female figure, I use both hip pads and a Roanyer breastplate to enhance it. In my humble opinion, these items are essential for achieving a truly feminine look. I use an E cup silicone breastplate from Royaner, and I’ve never looked back since. It bounces well and looks incredibly realistic! I also have some pretty basic foam hip pads, which I plan to upgrade to Roanyer ones soon.

When choosing your own, it’s good to consider your figure and cup size. I like to have a cup size that fits my size. I am also looking to acquire a C-cup so I have more options when it comes to putting uniforms together.

Wigs

Now we get to one of my favourite parts, wigs! There are thousands of styles, colours, lengths, and more to choose from. As I’m impatient, I prefer to get mine from Amazon because of the clear delivery times, though I think it’s also important to explore other providers. You must allocate a reasonable budget for all sections of this article, but especially for this part. A cheap wig can last 1 or 2 nights at most, so don’t waste your money on one that’s under £ 20, in my opinion.

I am naturally dark brown, so I gravitate towards those colours in wigs, though this does not mean that’s all I have. I’ve experimented with success with blonde with brown roots and dark ginger in the past. With and without bangs, though I think I prefer the ‘girl next door’ look, which bangs give you.

Make-Up

Now, let’s move on to another key section: makeup. I highly recommend purchasing a basic makeup set online, as many include all the essentials you’ll need to get started. A foundation, contour/highlight, blush, eyeliner, lipstick, and more are all necessary. 

Now, this article is not a tutorial on applying makeup, but there are thousands out there to read or watch online. Get yourself some free time, a good mirror, your makeup, and a lot of makeup wipes. Spend some good time practicing, though you will learn a lot naturally as you apply it each time you put everything together.

Some must-haves are the following (In my opinion, of course, haha):

• Liquid eyeliner- So much easier to apply than drawn-on eyeliner and a lot less painful!
• A glossy lipstick- Looks amazing in photographs
• Freckle pen- Easy to apply and really gives off that feminine energy 
• Many, many, many makeup sponges- just trust me on this one

Clothing

Now, let’s consider where you want to source your clothes from. I would say the first thing to do is take your measurements while you’ve your hip pads and breast plate on, so that you can determine your women’s size. However, this won’t be as simple as women’s sizes, which tend to vary from shop to shop.

As with my comment about buying wigs, you want to find a nice middle ground between price and quality. You don’t want cheap Halloween outfits, but you also don’t want to spend a lot on a single dress if you’re not sure of your style yet. Once you’re happy with your style and size, you can choose to spend more on outfits.

Again, I started by ordering on Amazon, as it’s easy to obtain and even easier to return if the clothes don’t fit. I’ve already put together some cute summer outfits from various items I bought online, and knowing returns are simple really helps.

Accessories

Accessories can significantly enhance your look in numerous ways. This can be anything from fake earrings to heart stamps and more. I adore my fake gold hoop earrings because I don’t have my ears pierced, and they look so relaxed when worn. Hair clips and scrunchies can also make your wig feel and look more real.

Belts and rings can also be useful. It’s always good to check what they match, as gold and silver pair amazingly with different colours, so don’t get caught out! Or do! It’s your choice at the end of the day! I’m a big fan of pastels myself.

Thigh-high socks and stockings/tights always pair well with a multitude of dresses, so it’s best to pick up a few in different colors to have options. And never forget that fishnet stockings always go down a treat. You literally can’t go wrong with them, trust me!

Conclusion

In conclusion, sisters, you should now hopefully have a simple guide to follow for those ready to dip their toes into crossdressing, finally. I know you might still feel nervous or have a racing heart just being here and reading this, but there’s nothing wrong with wanting to do this, and it’s clear your own heart has pulled you here.

Now, gather everything you need, put on some music or background noise, grab a cup of tea, and have some wipes handy. Spend a good few hours having guilt-free fun.