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Let’s talk about sissy style in general and, in particular, your fashion choices. Do you ever worry about how you look? If you do, I hope this blog post can help you relax a bit. You’re not alone. I’ve noticed that many girls have a common concern about style and fashion.

Here are some questions for you to consider:

  • What is the right look for a crossdresser, sissy or submissive transwoman?
  • Who decides the perfect sissy look?
  • How can you develop a fashion style that is right for you?

What is the ideal feminine appearance?Experienced Mistress Olivia Feminization and sissy training 1-800-601-6975

That’s a common concern, and I get it. No matter how you identify, it’s easy to fall into the “I need to look a certain way” kind of mindset. What do you do? Here are some things to think about as you consider your feminized ideal, what you should wear, and who can help with your style questions.

Clothing choices can signal all kinds of things about who you are and how you want to be treated. For example, think about what image you see in your mind when you hear the terms sissy slut or filly sissy. What about these terms: beautiful bride, feminized secretary, or sissy maid?

Figuring out your sissy style is an important part of any feminization journey. I think this trial and error is part of the fun of being feminine. Oh sure, you might get frustrated when you buy something that you think will look great only to find out you don’t like it. Don’t worry, this is part of the process of creating your look.

Who decides what a sissy should wear?

sissy style by Experienced Mistress Olivia 1-800-601-6975Do you ever feel compelled to conform to the sissy style seen in porn or feminization memes? Is there one right sissy style? Who gets to decide what the right look is for someone who is being transformed from male to female?

Your Mistress might tell you what to wear. I will pick out clothes for some ladies, but more often than not, I will help her develop her own sense of style. It’s okay if your style changes over time. My fashion choices continue to evolve. That’s part of the fun of fashion! How you look can (and should) change!

Sissy style questions and answers

Many sissy style questions are answered on my personal blog, Experienced Mistress, here on Sissy Style Magazine, and other places like the podcast I do with Ms Erika. It’s called The Weekly Hot Spot podcast.

I want to bring your attention to this question by a sissy: Why are skirts, heels, and frills considered traditionally feminine? Ms. Fiona joins us for the episode called Do you have this common worry about your sissy or femme style? These are some of the questions we want you to consider as you look at your style options.

Advice from a feminization Mistress

Ysissy slut training by Experienced Mistress Olivia 1-800-601-6975ou might already know exactly what you want to wear. Good for you! It’s still fun to have someone else with you; someone who loves to see what you buy and even go shopping with you. Remember, you don’t have to figure out what looks great on you on your own. A Mistress who understands your special circumstances can help with everything, including where to shop, how to buy your clothes discreetly, and even where to find cute shoes that fit!

You are not alone in your feminization

As you think about your ideal appearance, it’s always fun to have girl talk with someone who understands and encourages you. This sense of community is important for all of us. Sissy Kylie is a fan of The Weekly Hot Spot podcast, and she says:

“You and Ms. Erika make it so fun to be a sissy. You talk about practical things that really help! Thanks so much for being so awesome!”

Whether you know exactly what you want to wear or whether you’d like some fashion advice from your own personal shopper, you can get all the support you need from us. Don’t fall into the trap of looking at a sissy meme or image and thinking you have to have that exact look. It’s okay to develop your own sense of style, and a sissy Mistress can help!

Feel free to reach out to me. Send an email to: Olivia @ or give a call when you see me online. Let’s go shopping and have some fun!

Your Experienced Mistress,

Ms Olivia

Click above to hear Ms. Olivia