Ask Hannah!

I have been crossdressing in my mind since I was 15. I am now 45. I have been in clothes from time to time. I have been I a relationship for 8 months and I have told her everything. She is totally on board and thinks this will be really fun. I have never had any support and of course she doesn’t know where we should begin. We both agree we aren’t ready to hit dressing rooms to find my clothes. The thing I’m struggling with is my size. I’m 6’1 and 260. Definitely not a feminine figure but we want to get the ball rolling. My dream is to get to wear skirts and blouses. Can you help us out with this?

Congratulations on taking this step!  I am very excited for you, and I am very happy you were upfront and honest in your relationship.

Just a reminder, that there is no standard you must meet in order to be feminine.  No one is too tall, too short, too thin, too masculine, too… anything, to be beautiful.  Being comfortable and happy with who you are has more to do with how you feel than with how you look.  We all know women, whether they are cis or trans, who are all shapes and sizes and every single one of us is drop-dead gorgeous.

And you are too.

When you are ready to start building your wardrobe, you’ll find that determining your measurements is the most important thing you can know.


When I purchase “male” clothes (please note I don’t think there are such a thing as “male” clothes or “female” clothes, they’re just clothes), I purchase shirts that fit my shoulders and pants that are long enough and are the proper waist size. It’s pretty straightforward. Dresses are a different story. I have dresses that fit perfectly around my hips and waist, but don’t fit my shoulders and chest as I am wider on top than my middle. And of course every dressmaker has different sizing standards, as well. When shopping, you need to know your measurements, and yes, sometimes it is a flip of the coin when it comes to deciding to order based off of hips or waist measurements.

And remember, as the two embark on this… (ugh), journey, and it IS a journey, no matter how much I hate that word, you will both feel different things at different times and it is easy to let this overwhelm someone.  I write a lot about relationships on this site, but if you take anything from my writing, just be worth it and beware the fog.

Love, Hannah



9 thoughts on “Ask Hannah!

  1. to this person I am your same size and if you would like to cantact me about clothing sizes email me I am more than willing to help another girl on her journey.


  2. You were a crossdreamer, and now you are making your dreams come true! I was turned into a crossdreamer at age 3 and am now engaged in HRT. Congratulations to both of us! Ian Elliott


  3. I was walking with my dad and as we turned a corner, he stopped and said “I understand you’ve been playing with yourself down there. Better stop, or you’ll turn into a girl. That started my crossdreaming for life.


  4. Like Nicole above, I’m about your size. And I have no issues going out in public and doing what I want – shopping, dining, shows, etc. It does take practice, experience, and above all else confidence. But when the times comes, you’ll have to start developing the confidence from actually going out.

    Initially I was ordering on-line. I had a fair amount of success with JCPenney and their tall sizes. Just get your measurements as Hannah suggests and check the on-line size guide when you are shopping. And check the guide for each item you order – women’s sizes are not known for following any standards.

    One thing to remember is that for the same height, AMAB folks tend to have a longer torso and arms than an AFAB person, so watch sleeve (and to an extent body) length.

    Enjoy, and I hope to see you out at events in the future.


  5. hi, yes the brands are have diffrent sizes. for me being a full time t girl i get to be out and shop . but many times i have bought outfits that after i got home i was like what was i thinking. but i pass things on to others and shop at thrift stores so at least i dont have to pay full price and then its not such a big deal to pass them. i once lived cd life so i do understand.getting the confidence to be out. and i try to help my sisters out weather cd or t . and it helps when other have your back. all this online stuff and others i personly know have and are still helping me with my transition. always …maria


  6. Shopping for clothes has been a long evolution for me. I started in the thrift stores. If I found something I thought would fit, I never tried it on in the store. I’d just buy it hoping it would fit. I’d only approach the checkout if the cashier was young and female because I thought they were least likely to judge me. Nevertheless, I always had a story ready about it being “a gift for my girlfriend”.
    Thirty years later, I’m not sure if the world has changed but certainly I have. I shop in both boy and girl mode, try stuff on in the dressing rooms. I highly recommend Lane Bryant and Torrid. Not only do they have pretty things in sizes that accommodate people like us, but I’m sure I’m not the first male to go try on a pretty floral print ruffled frock there. Every salesclerk has welcomed me as just another “skirt enthusiast” (as I categorize myself), never as some sick pervert.
    I still have a story ready to tell, but now the stories are about the garden party where all the guests are in floral print maxi dresses or the Oscar party where everyone is in a cocktail frock.
    I hope you can let yourself be you! The agony of becoming that person is much easier than the agony of bottling up those feelings for half your life or longer!


  7. I got frustrated trying to find a dress that fit, so I decided to go with skirts and tops. You only need to fit half of you at a time. Making things match can be a challenge, but I figure “do not do two prints at the same time and you will be OK”. I have managed to find two dresses now – I will see what the future holds.


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