Ask Hannah!

Hi there Hannah. Just wanted to start out and say thank you for all you do. I am 31 male but I am finally starting to embrace that I enjoy dressing and possibly being female/transgender. Still unsure of some things as I am finally starting to talk about this and I am seeing a great therapist to help work things out. My questions is I am starting to actually dress and not just fantasize about it and just wondering what some good resources are to help learn how to dress and look more feminine? YouTube is great for somethings but like buying a wig and all the styles and different kinds also knowing how to do make up for my face it’s hard for me to know what would be good for me as everyone is so different? The great thing is I am also from MN so I think your insight would be amazing. Again thank you for all you do and for any advice.

Coming into your look is all about trial and error.  Coming into your look takes time, practice, mistakes and money.  It’s about discovering yourself.  It’s about finding what you like, what you are comfortable wearing and uncovering that part of you that might not get out very much.  It takes time and patience.  No one expects the first time they paint something that it will be a masterpiece.  Be easy on yourself the first (or even the fiftieth) time you dress up or apply makeup.  You might not look as fabulous as you want, but you’re getting there.

This is something you learn by doing.

Everyone has a different perspective on what is and what is not feminine.  The best, and the only way for you to find out what you like to wear is to try on a lot of clothes.  Some things you’ll try and like, others you won’t.  Some dresses make me feel like the prettiest girl in the mall, some make me feel like a man in a dress.  The important thing is for you to wear what you like.

A wig is not much different.  I tried a lot of different styles before I found the style that I like.  I’ve tried wavy styles, longer styles, styles with and without bangs before I found a style that is *me*.  It’s true there are resources out there that will help suggest what style may be best for your face, but really, who cares?  All that matters is what you like.  So, like clothing, try on a lot of different styles and you’ll find what works for you and what you like.

Makeup, like hair and clothes, also takes trial and error.  It took YEARS until I was happy with my look.  It took a lot of practice.  I made a lot of mistakes.  I spent a lot of money. Again, you achieve your look by doing.

So, here’s how you learn makeup. You could watch YouTube videos and learn from them but like buying clothes, everyone is different.  Everyone has different skin, different color, different tone.  What works for me might not work for you.  The easiest way to learn makeup is to have someone teach you.

Makeup is hard to get right.  There are still times when my eyeliner doesn’t look straight or my color correcting is a little off.  The best way to learn makeup is to schedule a makeover.  I know that sounds like the scariest thing in the world, and it is, but it’s the best way to start mastering your look.  Go to the experts, they will show you which products to use, which tones are best for your skin color and they will teach you how to apply makeup.  I’ve been doing my makeup for years and I probably had ten makeovers in the last twelve months and I still learn something new each time.  Remember, you aren’t the first or last t-girl your makeup artist will ever have. They are trained to help girls like us.  Makeup artists are also trained with advanced techniques, like contouring, which totally changed my life.

I have written pretty extensively about getting started and you can read about it here.  I cover topics like shaving, finding your measurements and more.

Since you live in Minnesota, I highly recommend you making a trip to Midwest Makeup Supply in Minneapolis and scheduling a makeup lesson.  While you’re there, I also suggest crossing the street to visit Sunny’s Hair and Wigs.  Both stores are very t-girl friendly.  I have other resources in Minnesota here, and I’d also encourage you to join the MN T-Girls.

Have fun, be safe!

Love, Hannah