Ease Into Crossdressing - The Crossdresser Report

Ease into Crossdressing

Are you someone who has just started thinking about trying crossdressing? Perhaps it is something that has intrigued you, but you don’t know where to start. I ran across an interesting video (sadly it is no longer up to view…) that I wish I had seen when I first gave crossdressing a try. It would have helped me to become comfortable with crossdressing much sooner. Continue reading for the step-by-step guide for easing into crossdressing.

Step 1: Buy Women’s Versions of What You Already Wear

Regardless of how slow or fast you want to experiment with crossdressing, especially in public, it all comes to answering a single question: How does one become comfortable doing it? For most people, it is a matter of taking it slowly, easing into crossdressing.

I think the easiest way to become comfortable is something that for many is difficult the first few times. This is to shop in the women’s clothing department. If you haven’t tried this yet and are like me, you will be more nervous than you were the first time you asked someone out on a date! As someone who has successfully navigated the women’s department, I can say with certainty that you will eventually become comfortable walking through that section of the store. I talk about this a bit in another article about The Power of One.

Your eventual goal isn’t only to walk through that section, though. Try buying something that looks like something you would wear as a male anyway. Go over to the sock section and buy a pair of athletic socks, for example. If you like wearing jeans, check out that section for ideas. You will be able to find jeans that look almost identical to what you already wear. Take them to the men’s changing room and see if they fit. Trust me, you’ll make it out alive!

Your goal, whether it takes a few days or many months, is to become comfortable buying and wearing in public items that you would be wearing anyway. Once you get to the point where you aren’t worried about drawing unwanted attention, you will be ready for the next step!

Step 2: Ease into Crossdressing by Wearing Casual Clothes

Now that you are comfortable shopping for women’s clothes and publicly wearing female versions of what you already wear, you are ready for the next big step. This is wearing women’s versions of what you already wear. These are items that look almost like wearing men’s clothes, but are slightly different.

An obvious example is t-shirts. You can find t-shirts that are almost, but not quite, identical between the men’s and women’s versions. For example, the end of the sleeve on a t-shirt for men is usually cut straight across. On a women’s t-shirt, it is slightly angled.

Men’s t-shirt with straight sleeves. Click to buy on Amazon
Women’s t-shirt with angled sleeves. Click to buy on Amazon

This is just one example of easing into crossdressing by replacing your casual male wardrobe with a slightly more feminine one, allowing yourself to become more comfortable wearing women’s clothes in public.

Step 3: Getting a Little Girly!

Once you have reached a level of comfort with wearing styles that are slightly more feminine than the male counterparts, you are ready to experiment with a girlier look. At first glance, these are still not super different than men’s clothing. They are definitely more girly though! But remember, you’ve already gotten comfortable with the clothes in step 2. The next step isn’t that much more difficult.

V-neck blouse for a slightly girlier look. Click to buy on Amazon
3/4 sleeve for a slightly girlier look. Click to buy on Amazon

There are several styles you can try. For example, you can wear a top that has a deeper v-neck. Notice in the example shown above that the hemline is a little longer on one side than the other. Both of these are feminine features, but the top isn’t overly different than what you’ve already become accustomed to wearing in step 2.

Another example of a girlier style is a blouse with 3/4 sleeves. Men’s clothes are usually either without sleeves (a tank top), have short sleeves (a t-shirt), or long sleeves (a dress shirt). A 3/4 sleeve is different than most men’s clothes, yet it really doesn’t look too different. For easing into crossdressing, this is one of my favorite styles when I want to go out in public while still presenting as a male.

Step 4: Feminine Casual Clothing

Now you are ready to try casual clothing for which there really isn’t a male counterpart. The fashions may be different because of the fabric, the cut, the color, or even the type of clothing. You may or may not feel comfortable wearing these in public without a wig, shapewear, or makeup. These will definitely draw attention to yourself if you present yourself otherwise as a male.

For example, you can ease into crossdressing by trying something that is from step 3, but rather than cotton fabric, you choose a velvet fabric. I have a velvet v-neck that it definitely looks feminine. To be truthful, I haven’t tried wearing this top in public because I am not quite ready yet. I can see myself giving it a try eventually.

Velvet V-Neck Blouse. Click to buy on Amazon
Leopard Print V-Neck Blouse. Click to buy on Amazon

For an example of a different cut, think about when you see women dressed for the winter. Much female outerwear is cut differently than men’s jackets. There is a tailored look to the waist, whereas men’s coats are straight up and down. The lapels may look longer and wider, and the coat itself longer. Sometimes they are lined with colorful fabric, and the hood may have fluffy fur around its edge. I have worn coats like this in public this winter, and I have gotten compliments from others.

Hooded Jacket with Tailored Waist. Click to buy on Amazon
Faux Leather Jacket. Click to buy on Amazon

The differences in color are easy to see. Pink and purple are obvious choices. For types of clothing that are different, think of leggings or capris with fancy pockets as examples.

Step 5: Fully Crossdressed

After going through the previous four steps, you are ready to venture into the world as a fully-dressed woman. Dresses, skirts, heels, hosiery, makeup, forms, and wigs – go for it, gal!

For myself, each of these steps was a source of fear and trepidation, followed by relief and enjoyment. The key is to take your time and push yourself to venture a little out of your comfort zone. By being successful over time, you’ll gain the confidence necessary to do anything you want!

How Will You Step into Crossdressing?

There you have it! Wherever you are in your crossdressing journey, you should be able to find a spot in these steps where you feel comfortable at the moment. If you are just getting started, wander into the women’s department and find yourself some basic women’s jeans to try. Already have some jeans? See if you can find some basic t-shirts that fit your personality. Just ease into crossdressing by gradually adding to your wardrobe, getting things that are a little more girly as you go along. Keep trying things that make you feel a little uncomfortable, and wear them until you don’t give it a second thought. You’ll be amazed at the progress you’ll make over the course of a year!

xoxoxo Sami

p.s., Here are some of other articles that can help you find the fashions you want.

What did you think about this article? How far are you along these crossdressing steps?  Leave a comment.

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Posted by Sami

Sami has been a part-time crossdresser for about 5 years. Although she still has a lot to learn herself, she is enjoying teaching new crossdressers tips that will hopefully help them on their adventure.
Besides enjoying her time with her family and working as a web developer, Sami loves to travel, make home improvements, and create jewelry in her spare time.
Read more about Sami by clicking her name.

12 thoughts on “Ease into Crossdressing”

  1. I support the baby step approach. I wear pantyhose daily. A few years ago I started to wear them under slacks without socks. Now I frequently wear pantyhose under my shorts.

  2. Yea I wear a size 6 pair of jeans because it’s difficult to find a pair of 27 inch waist in the mens department!!!

  3. i have just started thinking about crossdressing. I have been wearing women’s panties “for comfort” for a few months. (Small start) I need some courage to go the next step. My wife will not like or understand it so I have to remain the closet. Do I just have to give up or can I make it work?

    1. The general consensus is that one can try to give it up, but doing so doesn’t make life any easier. The urge to crossdress is always there in the background for most. In the long run it probably won’t be something you will want or be able to give up.

      Having said that, it is also true that many wives or girlfriends have a really hard time dealing with it. Being in the closet is probably the best thing to do for now.

      Be patient and bring up related topics from time to time. Who knows, perhaps over time she may become open minded enough to tolerate it. The key is to take it slowly. You didn’t realize this aspect of yourself overnight, so you can’t expect her to change overnight either.

      I am not a counselor, so your best bet is to seek one to help you through these issues. You can also try the workbook written by Dara Hoffman-Fox. Check it out at http://discoveryourgenderidentity.com

      Good luck to you!


      1. Alicia, I used a combination of trial & error and measurements. This is partly because each clothing manufacturer has different measurements for each size.

        The best thing is to be able to try on whatever it is you are wanting. That is hard to do nowadays due to the pandemic. If you are buying online, try to shop with sellers that show the measurements for each size. I really like eBay for this. Probably more than half do not post the measurements, but those that do are usually correct. Buy from those who have a return policy in case it doesn’t fit. When you finally find something that fits, take the measurements and use those when you shop online in the future.

  4. I love this idea ! I’ve been wanting to get started crossdressing for a few years but didn’t know where to start. I just ordered some woman’s tee shirts, shorts and jeans online to get started ! Thanks for the great article

  5. hi i love your site i was just wondering if you know of any organizations that offer financial help for crossdressers

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