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



Wear What Scares You

This month marks the fourth anniversary of the MN T-Girls.  As time passes I tend to look back more and reflect on how much things have changed, how far things have progressed or, in some cases, regressed.

At its heart, the MN T-Girls exists as a social and support group.  I wanted to create a group that socialized, that went out and did everyday things, such as having a nice dinner or going to the mall.  It is a group where one can feel safe when going out into the real world.  Many of us felt a mixture of emotions the first, or even the fiftieth time we left the house presenting as the gender we identified as.

I knew those emotions because I felt, and sometimes still do, feel them.  For years I was afraid to leave the house.  What was I afraid of?  A million things.  Afraid of my car breaking down and being stranded somewhere.  Afraid of being recognized, afraid of being harassed, threatened, laughed at, or worse.

I was afraid I was not beautiful.

There is a vague, unattainable goal of “passing” for some in our community.  Passing is when we, as transwomen, are seen as cis-women.  Although I can have flawless makeup and wear a beautiful dress, I still have wide shoulders, large hands and a deep voice.  In short, I have many physical characteristics that are normally associated with men.  Some of us want to pass because it’s validation and confirmation that our presentation is so amazing that most people would think we were born as females.  Some of us look at passing in a desire to be unrecognizable to people that we know who might see us.  Some of us just want to pass because it means we are as beautiful as the gender we identify as.

But passing is unattainable and vague, and it’s unattainable because it is so vague.  There is not a set of standards that one has to meet in order to be female, or to be beautiful.  Yes, I am tall (I am even taller in four inch heels), and height is often viewed as a male characteristic and thus “gives me away”.   But I have met cis-women who are taller than me.  I have met cis-women who have deeper voices than myself.  I have met cis-women with facial hair.

Are they not women because of those characteristics?  What decides what is feminine?  Who decides what is beauty?  Who decides who is beautiful?

No one.

Well, you do.

It’s not for anyone else to decide.  Once I realized that there was no such thing as passing, that there is no standard I had to meet in order to be beautiful, then my whole world change.  I was ready to go out.

16I was still nervous about the same things as before, with the exception of not feeling beautiful enough.  Instead of striving to pass, I wanted to blend in.  I did my best to blend in the first time I went out, which was about six years ago.  I was still learning makeup but my confidence was growing with each day.  I was tired of sitting around my living room and was ready to get out into the real world.  So, one Friday morning I woke up, did my makeup, got dressed and left the house.  The photo on the left is what I wore when I went out for the first time…a cute skirt, a colorful top, cardigan and black stockings.  I thought it was a perfect outfit for running errands.  For the next few months, I picked out outfits that, in my opinion, helped me blend in.  Blending in, I thought, was a form of protection.  There are those who have a fear and hatred of people who identify as transgender, and I didn’t want to draw a lot of attention to myself, lest I became a target for ridicule, violence, or worse.  Blending in became a sort of camouflage, in a way.

As I went out on a more regular basis, I realized that the world wasn’t as scary as I thought it would be.  If I was being laughed at and pointed towards, I didn’t notice it.  People were kind to me.  People complimented my outfit or the skill I had when it came to walking in heels.  My confidence grew.  My self-esteem grew.  Blending in, in those early days, gave me an opportunity to experience life as incognito as possible, considering I am a six foot tall (and taller in heels) transgirl.

As my wardrobe grew, I noticed the clothes I was buying were reflecting my growing confidence and courage.   I was buying less clothes that I felt helped me blend in and more clothes that, in the corner of mind, I would wear in public when I felt bolder.  It would take another year or so until the outfits I wore outside of the house moved from blending in to being bolder.  My wardrobe was expanding and was soon filling up with bright colors, bold patterns, higher heels and skirts that showed off all the hard work I put into on the Stairmaster at the gym.

Then one day I was done blending in.  I am not sure what triggered it, perhaps it was a beautiful day, or a new dress I couldn’t wait to wear.  Soon I was at the mall, at the art museum, getting makeovers and having coffee wearing dresses that I never thought I’d have the courage to wear in the real world.  Dresses with bright patterns, eye-catching designs and flowers.

A LOT of flowers.

I remember the day I wore the outfit pictured above. I was feeling particularly bold that afternoon and opted for a bright, tight pink dress with matching pink heels.  I looked at myself in every mirror I saw at the mall that day and marveled how it didn’t seem that long ago when I tried so hard to blend in, to not be noticed.  This outfit was about as far away as incognito as one could get.

These days I no longer try to blend in.  There’s not much in my closet that I am not comfortable wearing.  Of course, I still believe in dressing appropriately, I am not going to wear my leather dress and five inch stilettos to the grocery store, for example.

slit dress 3005701030035039

Looking back at these photos and remembering the past few years, I am amazed at the confidence I’ve gained in such a short time.  One of the reasons I formed the MN T-Girls was to show other transwomen that the world can be scary at first, but it’s really quite wonderful once you are out in it.  I understand the need and instinct to want to blend in, but standing out is liberating and amazing.  You may be surprised by how the world reacts and even embraces you.


There is a hashtag that I saw the other day that reads #wearwhatscaresyou and I really like that idea.  The idea of wearing a bright pink dress with sky-high heels terrified me a few years ago, but it’s one of my favorite outfits.  To me it screams confidence.

Wearing what scares you is a big step, and it took me a couple years to gain the confidence that I needed to do so.  But, like wearing high heels, it takes baby steps.  Getting a little push doesn’t hurt either.  I remember going to Pride and having to stop at the grocery store beforehand.  I was wearing a bright pink, polka dot dress to the festival and walking into the store wearing such a eye-catching outfit was a little scary at first.  The dress was perfect for a hot summer day at Pride, but very bold for a grocery store visit at 6:30am.  However, doing that was one of the little pushes I needed.

If you’re looking for a push, you may want to consider ‘Try-Day Friday’, a challenge that was started by Dia & Co, an online clothing company that provides their customers with new outfits that are designed to create confidence and help take fashion risks.

Despite many things happening in our country, I am feeling optimistic for our community.  We are making progress, socially and politically.  It’s not always been easy, but baby steps, you know?

I am also excited about your growing confidence.  Yes, yours.  Do something that scares you, wear something that scares you.

Love, Hannah










This Beautiful Season

0007Every year, as the end of spring begins to flirt with the first breath of summer, you see beauty everywhere.  The blossoming of flowers, the bluest sky imaginable and breathtaking sunsets.

This time of year you see girls getting ready for prom or to be in a wedding.  This season stirs up the desire to be beautiful, the intense pangs of jealousy.  When I was in high school I would see my female friends at a formal dance and couldn’t decide if I wanted to in love with them or if I wanted to look like them.  It was an intense…awakening, a turning point in my life.  Ultimately I would choose both.

This longing to pick out a beautiful gown, to find the perfect heels and to have an amazing makeover doesn’t ever go away.  It’s always there…but it’s never stronger or louder than right now.  I didn’t go to prom when I was a senior, but I wanted to.  I was dating a girl but we broke up a few weeks before the dance.  We had planned to go, and I lived vicariously through her as she recounted her experiences of shopping for the gown she ultimately would not wear.  If I was honest with myself,  I wanted to go to prom as a girl.  I wanted to spend weeks looking for a dress, the shoes and accessories.  I wanted the makeup and hair appointment, I wanted the photos, the going out to dinner at an upscale restaurant, the limo…everything.  I didn’t even want to go with someone, it would have been enough to just go, to be my own date.

When my high school days passed I had hopes of being a bridesmaid.  I wanted to experience going dress shopping with other girls, trying on countless gowns…just thinking about it makes me smile.

I am lucky to have experienced so many moments as Hannah, but it also hits me on occasion knowing that there are so many things that I likely never will.  I’ve had many makeovers, many photographs taken, and I have a beautiful wardrobe.  But being the most beautiful girl at a gala, in the room, the center of a dance floor, or a wedding photograph feels impossible.

I think you all know what I feel.

Love, Hannah

Saying Yes to the Dress, the Heels, the Skirts…

Is there anyone on the planet that has a bigger, more emotional relationship with clothes than a crossdresser?

As far back as I can remember, I remember the pangs of seeing a beautiful dress and just yearning to wear it.  As I got older the feeling just grew.  There was always a longing in my heart when I heard of girls in high school shopping for a prom dress, and later, listening to my friends talk about wedding gowns and bridesmaid dresses.

I think every one of us remembers the first time we wore a dress, the first time we walked in high heels, the first time we wore…anything and everything.

As I grew up and started to buy my own clothes, I remember the thrill of actually owning my own pair of panties, my first pair of heels.  Of course when I first moved out my wardrobe started to expand…and like many of us, the wardrobe ended up in the trash a short time later.  When we purged we all felt that this was it, we were never going to dress up again.  We could beat this, we could live without this.

Of course, we were all fooling ourselves.  It wasn’t long until we regretted the purge or until we were back at the mall, shopping all over again.  I purged more times than I would like to remember.  I have thrown away so many dresses and heels that I regret.

When I was in mid-20’s, I realized I was never going to change and I finally accepted that this is who I am.  My wardrobe started to steadily grow over the next few years and then I met the girl I married.  After a few months of dating, I told her about everything.  It was a shock to her but I was glad I was honest with her.  I knew I wanted to marry her and I knew I had to be upfront with her.  A few days before we moved in with each other, I purged for the last time.

Of course, it wasn’t long until I started buying panties again, but I was honest with her.  Soon I started to grow a wardrobe again and I never purged again.

Until tonight.

Kind of.

A little over two years ago, I decided it was time to make some changes and I cut back drastically on my drinking, started to exercise more and lost fifty pounds and I have kept it over since then.  I also dropped from a size 20 to a size 12.  I needed new clothes and my wardrobe started to grow again.

I cleared out my closet and I wondered what I should do with the clothes that didn’t fit anymore.  I finally found a perfect home for the clothes and I am excited it will help other t-girls.  More on this later.

Tonight I sorted the clothes that were going to be donated and it was very emotional.  I found the first dress that I bought years ago when I started my wardrobe for the final time, I found the dress I wore the first night I went out, the skirt I wore when I went out for the first time I went out during the day, the first dress my wife bought for me…

I am lucky to have the life, the wife and the clothes I have.  I am glad these clothes will go to other t-girls that will love them as much as I do.   I wanted to take a look back on some of these outfits and reflect on how important they were in helping me become…ME.  These clothes are a part of me and I truly loved them.

Love, Hannah