Many girls wonder what they need to get started with their crossdressing wardrobe. I’m here to give you a few ideas. Not how I started, but more so on where you might take those first steps as a beginner who’s hooked on the thrill of crossdressing.

I would look to begin, regarding the wardrobe worn on the exterior, with a little black dress (a girl’s essential) and a pair of black ankle strapped closed-toe pumps which could also be dressed up with other dresses or down with jeans.

Speaking of jeans, purchase a dark-washed pair of jeans. As dark as you can possibly find – why, you ask? Because dark colored jeans never seem to go out of style, and they just have a very classy look to them. Make sure they are extremely tapered at the bottom of your legs and come with plenty of spandex or elastane for the stretch and fit factor. Also, try to find a high-waisted jean, which is long enough at the bottom to roll up a notch or two for another optional, sexy look. The high-waisted jeans, which are getting harder and harder to find, are the ones that will enhance your figure, especially when wearing butt or hip pads underneath.

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You’ll want have on hand both a white girly top/blouse and a black one as well, which have a design to them so they can be dressed-up with skirts or dressed-down with jeans or shorts. They work best if solid in color so as to make them as versatile as possible.

A plaid pencil skirt, slightly above the knee is essential to any lady’s wardrobe. Most of the time, these skirts are to be paired with a black or white top, jet black hose, and those black ankle strapped pumps noted above.

For your first selection of fall and winter clothing as a girl, I would suggest a black wool skater skirt worn with black opaque tights. This type skirt and these tights can hide a myriad of flaws you may have in your legs or midsection. Pair the above two essentials with a firm fitting turtleneck or crew neck top, and then try to find a wide elastic belt to complete the look and add to the curves! As far as pairing footwear in the winter with this style of outfit, it’s hard to beat a black suede pair of ankle booties. They are not only cute and sexy; they are also comfy and easy to walk in!

Two last items to add to the essentials in the beginning are a button up top – preferably solid white or black with or without polka dots. This type of top can be dressed up with any type of skirt or dressed down with jeans or slacks. And speaking of slacks, a pair of nice fitting solid black slacks with tapered legs narrowing at the bottom would be the last of the essential items I would add to the beginnings of a cute, classy, and pretty new wardrobe.

I won’t be addressing underwear or panties in this article. I will tell you once you get hooked on your favorite style and brand name of panties, you won’t be able to stop buying them! Panties are highly addictive and so comfortable when compared to men’s underwear! I haven’t worn a pair of men’s underwear in over eight years! My two favorite brands are Ellen Tracy and Vince Camuto.  

Well girls, that’s my suggestions for the essentials in building a beginning wardrobe. I’m sure you have plenty of questions regarding this topic or other wardrobe help needs in general. If you have any questions, please feel free to send them to me in a private message!


Love y’all! XOXOXO Scarlett

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I love the thrill of cross dressing and based on the CDH girls' comments in response to my posted photos, I must be pretty good at exploring the feminine side of myself. I find it sexy, sensual, exciting, challenging, and ever changing. I'm so very blessed now to have as much money as I want to spend on Scarlett and can now, for the very first time in fifteen years, actually purchase dresses, tops, and skirts while shopping with my wife! I never thought that would ever come to fruition! I can now store all of Scarlett's things in our huge dream home when just a short period of time ago, it would all have to be kept in a temperature controlled storage unit. I love Crossdressing Heaven and know it's the classiest and most tasteful cross dressing site on line. All the girls are full of support and encouragement and if folks come to the site with alternate motives that aren't in line with our founders rules and regulations, they are quickly deleted from our site. Vanessa Law, our founder, keeps this site classy at all times. She has much help from her Ambassadors, Chat Room Monitors, Photo Monitors, Article Editors, and many more personnel to keep this site classy, encouraging, and supportive.
  1. Author
    Scarlett398 2 months ago

    Abby, compliments and comments like yours and so many other girls her on CDH make the time, effort, and energy to accomplish those long winded photo shoots by myself here in our dream home well worth the effort. You wouldn’t believe what goes into my photo shoots but it’s a heck of a lot of work! Usually it takes close to between 12 and 14 hours to complete a session with between 200 and 500 photos taken during each shoot. I take my cross dressing very seriously but have a blast doing it! You can tell by my ear to ear smiles in my photos how much pleasure I get out of being Scarlett whenever I can. I love being a girl and only have an opportunity to get my total girl on as Scarlett one a week or once every other week. And I can’t do it while in the presence of my sexy redhead wife. She’s come miles forward with her acceptance of the femme side of me but she much prefers the “Handsome Husband” side of me rather than the “Cute, Sexy, Pretty, and Classy Scarlett” side of me. Abby, I actually think she’s a bit jealous of Scarlett. Because she doesn’t even want to see any photos of Scarlett and I think she thinks Scarlett is actually prettier than she is even though she’s gorgeous and we both have the exact same style of clothing, makeup, footwear, and jewelry! If you went into her closets and then went into Scarlett’s closets, you couldn’t tell which ones belonged to Scarlett and which ones belonged to her!

    You, Abby, and the other girls on this site inspire me to write and edit those articles in the Article Section in addition to my photo shoots. You can’t tell which ones I edited because my name doesn’t appear in or near the article if I was the editor, however, they are articles that usually generate a generous supply of responses from our CDH readers.

    The articles I personally write are usually instructional articles filled with knowledge and tips I share with the CDH girls based on my decades of experience, trial and error, and hours of studying makeup videos through Google which takes you to You Tube videos where I learned every single bit of my makeup skills. You see, Abby, I’ve never been to a pro makeup artist in person for a professional makeover. I respect all of the girls who go there and do that. However, everything you ever wanted to know about the application of any type of makeup and the use of all of those makeup brushes critical to turning out a professional job on your face with the application process – it’s all on line and the videos are very short and exceptionally valuable.

    Now Abby, I can tell from your short and lovely note to me that Abby has some formal education behind her. It seems as though you have an astute command of the English Language. I want to know more about you like how much formal education you have, where did you accomplish the education, and what type of careers you were involved with throughout your working life. I love learning more about the girls I serve as an inspiration to. I love hearing that I’m the reason they are inspired to no longer have feelings of guilt or shame associated with this wonderful thrill of cross dressing of ours. And you know from cross dressing as long as we have, once you start it’s almost impossible to stop!

    Thanks again for the friend request and this sweet note you sent to me. Send me a private message anytime you have a question about cross dressing or my background. My entire life is an open and extremely interesting one that’s still making new chapters at age 64!

    Have a super weekend, Girl Friend!

    XOXOXO Scarlett

  2. Nicole Dalton 2 months ago

    Great ideas Scarlett!

    • Author
      Scarlett398 2 months ago

      Thanks Nicole! It really works for me and the girls I show my photos too can’t wait till they see the next batch!

      I can’t go to their place of work without a batch of Scarlett photos!

      XOXOXO Scarlett

  3. Yael Lyons 2 months ago

    Thank you for the post Scarlett,

    All I can say is Wow. That is a lot of great information.

    By the way that is a great outfit.


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