Crossdressing Tips for Mature Crossdressers

04/29/2023 BY Clea

Are you a crossdresser who is about to reach the big age of 50 or up? If so, you’ll be happy to know that there are actually plenty of things you can do to ensure your continued pleasure in crossdressing.


 Crossdressing Tips for Mature Crossdressers


Crossdressing can be a rewarding and liberating experience for people of all ages, but it can also present unique challenges for mature crossdressers. Mature crossdressers who have been around the ropes and through the full circle of the swinging lifestyle will know the frustration of having their cross-dressing passion slowly declining. But that doesn’t have to happen! Remember that age is just a number!



Whether you’re just starting out or you’re a seasoned pro, here are some tips to help you feel confident and comfortable in your crossdressing journey.


Find the right clothes


 Crossdressing Tips for Mature Crossdressers


As a mature crossdresser, it’s important to find clothing that flatters your body type and makes you feel comfortable. Look for clothes that are tailored to your shape and size, and try to avoid anything that’s too tight or revealing. Classic styles like pencil skirts, blouses, and cardigans can be timeless and elegant, while more casual pieces like jeans and t-shirts can be dressed up with the right accessories. Clothing that is too tight or too loose can be unflattering and uncomfortable. Look for pieces that skim your body and accentuate your best features without clinging too tightly. You may also want to consider shapewear to smooth out any bumps or lumps and create a more streamlined silhouette.


 Crossdressing Tips for Mature Crossdressers


When it comes to style, opt for timeless pieces that will never go out of fashion. Classic pieces like tailored blazers, well-fitted trousers, and crisp white shirts are versatile and can be dressed up or down depending on the occasion. Additionally, don’t be afraid to experiment with color and prints, but stick to ones that suit your skin tone and personal style. Also, accessories can also be a great way to elevate your look as a mature crossdresser. Statement jewelry, scarves, and hats can add interest to even the simplest outfit. Finally, invest in good quality shoes that are comfortable and stylish. Flats, loafers, and low heels are all great options for mature crossdressers.


Choose the right makeup


Crossdressing Tips for Mature Crossdressers


Choosing the right makeup as a mature crossdresser is crucial for enhancing your natural beauty and feeling confident in your appearance. As we age, our skin changes and it’s important to adjust our makeup routine accordingly. Makeup can be a powerful tool for crossdressers, but it’s important to choose the right products and techniques for your age and skin type. Consider investing in high-quality skincare products to keep your skin looking fresh and youthful, and choose makeup that’s appropriate for your age and skin tone. Stick to natural-looking shades for a subtle and sophisticated look.


Crossdressing Tips for Mature Crossdressers


Start with a good skincare routine that includes moisturizing and sun protection. As we age, our skin becomes drier, so using a moisturizer daily can help keep your skin hydrated and prevent wrinkles. Sun protection is also important as it can help prevent further damage and keep your skin looking youthful. When it comes to makeup, opt for a lightweight foundation or tinted moisturizer that matches your skin tone. Avoid heavy powders or thick creams that can settle into fine lines and wrinkles. Instead, use a concealer to cover any blemishes or dark circles under the eyes. For eyes, stick to neutral eyeshadows and avoid glitter or shimmer, which can draw attention to fine lines and wrinkles. A neutral, matte eyeshadow can create a soft, natural look. Use a waterproof mascara to prevent smudging and flaking throughout the day. Lips should be kept soft and moisturized. As we age, our lips can become thinner and drier, so avoid matte or long-wearing lipsticks that can accentuate these changes. Instead, opt for a hydrating lip balm or gloss that adds a touch of color and shine


Practice good posture


 Crossdressing Tips for Mature Crossdressers


Good posture is key to looking confident and feminine as a crossdresser. Practice standing up straight with your shoulders back and your head held high. You can also try yoga or Pilates to improve your posture and flexibility. Practicing good posture is important for people of all ages, including crossdressers ages 50 and up. Good posture can help prevent a variety of health problems, including back pain, neck pain, and headaches, which can be particularly important for people who wear clothing that may not fit their body in a typical way.


 Crossdressing Tips for Mature Crossdressers


Mature crossdressers may also experience changes in their body as they age, such as decreased muscle tone and flexibility, which can make maintaining good posture more challenging. However, with practice, it is possible to improve posture and maintain good health. Some tips for improving posture include:


Sit and stand up straight: Keep your shoulders back and your chest forward.


Keep your feet flat on the ground: Avoid crossing your legs or ankles while sitting.


Use a chair with good back support: Make sure your chair has good lumbar support.


Take frequent breaks: If you are sitting or standing for long periods of time, take breaks to stretch and move around.


Strengthen your core muscles: Exercises that strengthen your core muscles can help improve posture.


Consider shapewear


Crossdressing Tips for Mature Crossdressers


As crossdressers age, we may experience changes in our body shape and muscle tone, which can make it more difficult to achieve the desired look when crossdressing.  Shapewear can help create a smoother silhouette, enhance curves, and provide support where needed, which can be particularly beneficial for crossdressers who may be looking to present a more feminine appearance. You might also consider investing in breast forms or padding to create a more realistic bustline.


 Crossdressing Tips for Mature Crossdressers


Shapewear can help by providing a foundation to build upon, smoothing out bumps and bulges, and creating a more streamlined silhouette. When choosing shapewear, it is important to consider factors such as comfort, fit, and level of compression. Crossdressers aged 50 and up may have different needs and preferences when it comes to shapewear, such as choosing garments that provide support for the lower back or that are made from breathable materials to help regulate body temperature. It is also important to use shapewear in moderation and to choose styles that do not restrict movement or circulation. Overuse of shapewear can lead to discomfort, skin irritation, and even health problems such as breathing difficulties or digestive issues.


Pay attention to your hair


 Crossdressing Tips for Mature Crossdressers


Your hairstyle can make a big difference in how you look and feel as a crossdresser. Consider getting a professional haircut that flatters your face shape and features. You might also experiment with wigs or hair extensions to achieve a more feminine look. As a mature crossdresser over 50, paying attention to your hair is an important aspect of your overall appearance. Your hairstyle can complement your outfits, enhance your facial features, and even help you feel more confident.


 Crossdressing Tips for Mature Crossdressers


When choosing a hairstyle, consider your face shape and hair texture, as well as your personal style and preferences. A shorter hairstyle can be a great option for mature crossdressers, as it can be easier to manage and maintain. However, longer hairstyles can also be flattering if styled properly. If you’re not sure what hairstyle or color is right for you, consider consulting with a professional hairstylist. They can help you choose a style that flatters your face and complements your personal style.


 Crossdressing Tips for Mature Crossdressers


It’s also important to pay attention to hair color and maintenance. Gray hair can be stylish and sophisticated, but it’s important to keep it healthy and well-groomed. Regular trims and conditioning treatments can help keep your hair looking its best. You may also want to consider using styling products, such as gels or mousses, to enhance your hair’s natural texture and add volume.


Find a supportive community


Crossdressing Tips for Mature Crossdressers


Crossdressing can be a solitary experience, but it doesn’t have to be. Consider joining a support group if you haven’t. Finding a supportive community can be an important part of your journey. Connecting with others who share your interests and experiences can help you feel less isolated and more empowered in your crossdressing. There are many ways to find a supportive community as a mature crossdresser. One option is to join a local crossdressing group or club, which can provide opportunities for socializing, networking, and learning about new fashion and makeup tips.


Crossdressing Tips for Mature Crossdressers


Online forums and social media groups can also be a great way to connect with other mature crossdressers and share your experiences. These communities can provide a safe and supportive space to ask questions, seek advice, and share your own insights and experiences. Attending crossdressing events, such as conventions or drag shows, can also be a great way to connect with others in the community and celebrate your love of crossdressing. Remember that finding a supportive community takes time and effort, and it’s important to be patient and open-minded. It may take some trial and error to find a group or community that feels like a good fit for you.




Crossdressing Tips for Mature Crossdressers


Crossdressing can be a rewarding and fulfilling experience at any age, and with these tips, mature crossdressers can feel confident and comfortable in their own skin. Remember to always be true to yourself and to enjoy the journey.

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  1. I am 77 soon 78, and a cross dressing husband or a trans female, not sure. I am at a point in my life that I’m not sure what to do with my life. I try to fight the fem side I have but she is winning and I have no one to turn to in my life for support. I just want to disappear,

  2. Please remember that you are worthy of love and respect, regardless of your gender identity or expression. Your life has value, and you have a unique perspective to offer the world.

  3. I’m a mature crossdresser who does so for sexual arousel and feeling relaxed.
    I have feelings to have sex with another crossdresser but never have. I still have interest in women but have no confidence in trying to have a relationship with them .

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