Wednesday, June 12, 2024

The Right Dress for Success

What dress styles are best for crossdressing?

When it comes to crossdressing, choosing the right dress style can make all the difference. Here are some flattering options:

A-Line Dresses: A-line dresses gently flare out from the waist, creating a feminine silhouette. They’re versatile and suit most body types.

Wrap Dresses: These dresses wrap around your body, emphasizing the waist and creating an hourglass shape. They’re comfortable and flattering.

Empire-Waist Dresses: Empire-waist dresses have a high waistline just below the bust. They flow gracefully over the hips, making them ideal for crossdressers.

Fit-and-Flare Dresses. These dresses are fitted at the waist and flare out at the hips. They accentuate curves and create a feminine look.

Sheath Dresses: Sheath dresses are form-fitting and elegant. They hug your body, emphasizing your figure.

Remember, confidence is key! Choose styles that make you feel comfortable and beautiful.

A follow-up question: What age should a crossdresser stop wearing short skirts?

There’s no strict age limit for wearing short skirts—it’s all about personal comfort and style. Many crossdressers continue to wear short skirts well into their later years. Here are some perspectives:

Confidence Matters: If you feel confident and comfortable in short skirts, go ahead! Confidence is ageless.

Style and Occasion: Consider the context. Short skirts can be chic and stylish if paired with the right top and accessories. Opt for smart, age-appropriate combinations.

Safety: Be mindful of safety—especially when bending or sitting. Some crossdressers choose longer skirts for practical reasons.

Individual Choice: Ultimately, it’s your choice. If you love short skirts, wear them proudly, regardless of age.

Remember, fashion knows no boundaries!

Source: White House Black Market
A Fit-and-Flare dress from White House Black Market

Mrs. Fred Flintstone and Mrs. Barney Rubble!
Mrs. Fred Flintstone and Mrs. Barney Rubble!


  1. AnonymousJune 12, 2024

    I was once told I had lucky legs... Lucky they don't break..!
    You need good legs to wear short skirts so I always have mine either on or just below the knee.

  2. Last Sunday I wore a slightly above the knee dress with sandals to church. Some trouser wearing woman blurted out, "Nice legs, John".


  3. AnonymousJune 12, 2024

    Your narrative resonated with me. I grappled with buy a different style dress on Monday. I bought it and I love it. Now I might try some other styles.

    For lengths I am fortunate to be able to wear below knee, at knee and a “long”mini skirts.

  4. AnonymousJune 14, 2024

    My favorite dresses are all empire waists. They work best to obscure a not so feminine hour glass form. Length wise, it's knee length =/- an inch or two. Midi's are fine too. Once I was attracted to a display of ankle length empire waist sun dresses at Sears. I figured as a six footer the dresses would rise way up, but to my amazement they hit the top of my feet. If a five foot six/seven woman wore them, I am sure the ladies would have tripped in them or clean dust off the floor.