Ask Hannah!

I’m trying to figure out how to dress the best I can, I have had a little practice but I would like some guidance

Presenting en femme is… well, hm. It can mean a million tiny things.

You need to be prepared mentally, emotionally and yes, financially. Crossdressing takes time, money, and patience.

The first time you put on a wig may not be the magical transformation your heart is longing for. The first pair of panties you wear may not fit. The first step in stilettos may result in a tumble. Be patient and be kind to yourself.

But you also need to be specific. What are your goals? Are you looking for guidance on how to find breast forms? Do you need help with blending your foundation? Are you looking for stores to buy heels? Do you need to be taught the differences between a heat-resistant wig and a synthetic blend wig? Are you needing guidance on how to shave your legs?

When it comes to crossdressing technically anything you wear that is traditionally not associated with “boy clothes” is crossdressing. This could include painting your toenails or wearing panties or dressing wig to heels.

If someone needs help I am happy to assist. You may find this helpful. But the best way I can offer guidance is if I know what someone needs help with specifically.

If someone needs help with “all of it”, then girl you better be ready to work. You better be ready to strut out of your comfort zone. You better be financially ready. You better be ready to commit. Breast forms, quality wigs, makeup, a wardrobe, shapewear… none of these things are cheap. And for a lot of these things you get what you pay for.

But of course, makeup, dresses, curves… none of these things are necessary to be femme. Girls can wear whatever they want, whether it is winged eyeliner and a pink dress or comfy clothes and no makeup.

If you are just starting out, I will absolutely encourage you to go slooooooow. Beware the PINK FOG. Crossdressing can absolutely bankrupt you if you are not thinking clearly. Do not hop online and spend hundreds of dollars on everything you think you need.

When it comes to clothes, you will absolutely want to know your measurements. You might wear a men’s large t-shirt, but what does that mean when it comes to your dress size? Dress sizes are all over. Some designers think I am a ‘medium’, but Forever 21 says I am a size 20.

I do not like Forever 21.

You may find this visual helpful.

I also wear different sizes depending on my forms. I have some dresses that zip up easy-peasy, but it’s not so easy-peasy when I am wearing my breast forms. Stockings glide up my legs, but if I am wearing my thigh pads, I need to go with a larger size.

As I strutted and stumbled along my gender journey I have had to leave my comfort zone sooooo many times. I still do. But… well, I HAD to if I wanted to learn what I wanted to learn. Whether it was a bra fitting or a makeup lesson or even just stopping at the gas station, I have done so many things and had so many interactions I never thought I would have.

Your journey begins the moment you are willing to step out of your comfort zone. Never before. If you think “I can’t do *that*”, well, you’re right.

At least not yet.

Getting out of your comfort zone doesn’t always mean going to the mall en femme. This can be something as small as saying out loud (even if no one hears) “I am a crossdresser.” Sometimes your journey begins with buying a single pair of panties. It’s such a cliché but adventures begin with a small, humble step.

It would be nice if someone came to your house and showed you how to do makeup but that’s not very realistic. It would be wonderful if every dress you saw fit, but you may find yourself needing to use a dressing room before you buy an outfit.

Crossdressing/changing your gender presentation is…. HUGE. It’s a lot of tiny and giant steps. Think about what you want to learn. Be specific. Be realistic. Be patient. Be kind to yourself.

And goddammit, have the time of your life. 🙂

Love, Hannah

Have a question for me?  Oh yes you do.  Ask me here!

2 thoughts on “Ask Hannah!

  1. Hello Hanna i just love all your post, gives me ideas and hope and what to wear and not wear. yes it is not cheap to buy female clothing or breast forms, make up, wig, nylons, panties, perfume, ear rings. heels, nail polish, cover up and foundation. lots of colors to choose from but has to be the color of your skin to match. when dressing up its dressing up to blend in. and yes society is not to keen on cross dressers still but slowly society is. i am still in the closet but i did go out dressed up to a Buffalo Bells meeting years ago and i had a hell of a time being the real me. thanks for reading my post Lucinda

    Liked by 1 person

  2. My first advice is “people watch”. Go to the places you might want to go as a woman and observe. What are the women around your age wearing? Look at their purses and accessories. Look at their hair and makeup.

    Try on a lot of outfits. Go to a thrift store or JC Penneys or Macy’s and just try stuff on. If you have a female friend even better. Just see how things fit and what styles and colors lok good on you. You dont have to buy everything (or sometimes anything!!); just see how things look on you.

    Get a makeover. Ask you makeup artist what products they are using, the shade, and what tools and techniques they are using to apply. Take notes!!

    Remember, all those GG ladies out there have been learning makeup, and style and fashion since childhood.

    Liked by 1 person

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