If you’re just starting your crossdressing journey, it can be an exciting and intimidating time.
There are so many things to consider… from choosing the right clothes, to learning how to do your makeup, to figuring out how to express your female self in a way that feels right to you.
In this blog post, I share 10 tips for beginner crossdressers to help you look and feel your best. Read on to learn more!
1. Invest In a Good Wig
Investing in a good wig is a great first step for any beginner crossdresser.
A wig can instantly transform your appearance, and it also gives you the opportunity to try out different hairstyles and looks.
Investing in a good wig is a great first step for any beginner crossdresser.
A wig can instantly transform your appearance, and it also gives you the opportunity to try out different hairstyles and looks.
2. Learn Basic Makeup Skills
If you’re just getting started, makeup can seem overwhelming. But hang in there because makeup is one of the most important tools for feminizing your appearance.
Fortunately, there are lots of online tutorials that can guide you.
Don’t worry about complicated makeup techniques (like false eyelashes or contouring) in the beginning. Instead, focus on lipstick and simple eye makeup, such as eyeshadow and mascara.
These are easy to apply and will glamorize your appearance – even if your technique isn’t perfect.
3. Get a Clean Shave
Shaving your face is important to looking feminine as feminine as possible. Use a good razor and shave right before getting dressed so you can have a fresh, clean face with no trace of stubble.
Obviously, it would be ideal to shave your body as well. You’ll look more feminine, plus female clothing feels softer against smooth, shaved skin.
Since hair removal is one of those areas that can easily go wrong, be sure to check out my article on 5 Male to Female Hair Removal Mistakes to Avoid.
4. Create Feminine Curves
Feminine curves are undeniably appealing. That’s why most every crossdresser will want to begin their journey with breast forms.
Invest in a pair of breast forms that are appropriate for your body proportions. (Not too big and not too small.)
Silicone breast forms can cost hundreds of dollars, but if you’re just getting started, look for an inexpensive pair of breast forms on Amazon or Ebay.
Hip and butt pads are the key to creating lower body curves, but this is something that you can invest in later down the line.
5. Know Your Measurements
If you prefer to shop online, as many beginner crossdressers do, then knowing your body measurements is crucial.
Men’s and women’s clothing is sized differently. Plus, sizing varies between brands. If you know your body measurements, you can check sizing charts before ordering clothing online. This will save you from many sizing mistakes.
To get your measurements, use a measuring tape and measure the following areas:
Bust (with and without breast forms)
Chest
Waist
Hips
Here are some additional tips to ensure that you are taking accurate body measurements:
The tape measure should be held snug, but not too tight.
Be sure to keep the tape measure parallel to the floor.
Take your measurements in front of a mirror to ensure the tape measure is level.
Even better, have somebody else take your measurements for you.
6. Wear Clothes That Make You Feel Good
Now for the fun part – shopping!
When you are starting crossdressing, it’s all about experimenting so look for clothes that appeal to you. Don’t buy anything boring or blah just because it’s what you think you “should” wear.
Also, don’t overspend on expensive clothing while you are still figuring out your style. Thrift stores, consignment shops, and Ebay are great options for inexpensive clothes.
Feeling good also has to do with being comfortable, so don’t wear super tight corsets, 5 inch stilettos, or anything else that feels like torture. (Unless, of course, you want to!)
7. Choose The Right Shoes
Shoes are important for completing your look. High heels can instantly make you feel. more feminine and attractive, even if you are just staying in the house.
Aside from their obvious sex appeal, heels also have an effect on your posture and give you a more feminine hip sway when you walk.
If you’re on a limited budget, invest in a pair of basic black or nude pumps that will go with everything. Heels below 3″ tend to be easier to walk in if you’re just getting started.
Finding women’s shoes in your size can be challenging. Check out my post on Transgender / Crossdressing Shoes: Top Places to Find Women’s Shoes in Your Size for my top shoe shopping recommendations.
8. Step Out Confidently (When You’re Ready)
If you are like most beginner crossdressers, your journey will start in the privacy of your own home.
But eventually, you might reach a point where you want to step out publicly. This is an exciting step and can be great validation for your female self.
Plan ahead to ensure that it’s a good experience. If it’s your first time out, go somewhere where people are used to seeing crossdressers and transgender women (like an LGTBQ friendly bar). You may also want to bring a friend or spouse for support.
9. Don’t Worry About Passing
“Passing as a woman” is seen as the holy grail for many crossdressers and transgender women – however, this simply isn’t practical for most people.
Instead, your goal should be to feel comfortable in your own skin. It’s ok to want to look your best as a woman, but this doesn’t mean you have to look exactly like a cisgender woman.
I believe you should be proud to be seen as an attractive and stylish crossdresser!
10. Experiment And Have Fun
Above all, have fun as you begin your crossdressing journey! Realize that you will make mistakes. Your hair, makeup, and fashion skills might not be perfect on the first go and that’s ok.
You will get better as you practice and discover your own unique style. So, enjoy the process, experiment, and most of all, HAVE FUN!
Are you a beginner crossdresser?
I hope you found these tips helpful – and that they give you the confidence to express your fab femme self!
Love Sissy Family
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