You are never too young or too old to be your best female self.
But what does that mean when it comes to dressing age appropriately as a transgender woman or crossdresser?
We’ve all seen older women dressed like teenagers… and the attention they attract usually isn’t positive.
Does that mean you have to dress like an old frump after a certain age?
I believe most of the “dress for your age” rules are silly and outdated…
That said, there ARE some guidelines worth keeping in mind.
In this blog post, I share tips on how to look classy and feminine at every age.
Your 20s or Younger
20s: Transgender style inspiration
20s: Transgender style tips
- Your 20s are a time to play with trends and be adventurous. You’re still discovering your style, so take risks and have fun!
- You’re not a kid anymore, so avoid adolescent details like glitter, rhinestones, or cartoony prints.
- You can get away with short skirts and body-baring styles, but be careful not to cross the line from sexy to slutty. Good taste is a fashion DO at any age.
30s: Transgender style inspiration
30s: Transgender style tips
- Your 30s are the time to start adding a touch of sophistication to your look.
- You can still have fun, but it’s time to uplevel your look by dressing less casually than you did in your 20s.
- This is the perfect time to start building a wardrobe of classics while continuing to play with trendy items.
40s: Transgender style inspiration
40s: Transgender style tips
- This is the age to start thinking about dressing in more tailored styles. Consider classic, clean shapes in bold colors or prints for added impact.
- Go for simplicity rather than complicated details. From now on, your look should be clean, classy and sophisticated.
- There’s no reason to turn down your sex appeal once you hit 40. But instead of baring it all, show off one part of your body and keep the rest covered.
50s: Transgender style inspiration
50s: Transgender style tips
- Now’s the time to start highlighting your face instead of your body. (Though if you have a body like Candis Cayne, throw this rule out the window!)
- It’s especially important to wear clothes that fit well. Choose tailored styles that skim your body instead of clinging.
- As you get older, your clothes should get simpler. But simple doesn’t have to mean boring! Accessorize with bold jewelry, gorgeous bags, and great shoes.
Your 60s and Beyond
60s+: Transgender style inspiration
60s+: Transgender style tips
- By now you know yourself well and are past trying to look like a 30-year-old.
- Much like a woman in her 50s, it’s best to stick to the classics, with lots of interesting jewelry and other accessories to liven up your face and wardrobe.
- Invest in good quality shoes, handbags, and jewelry so you can enjoy them through this decade and beyond.
- No matter how far past 60 you are, you NEVER have to dress in frumpy old lady clothes!
NOW is the Perfect Time to Be Your Best Female Self!
The most important thing to know is that you can look beautiful and feminine at any age. NOW is the perfect time to be your best female self, so let’s celebrate your journey!
On that note, I’d love to hear from you…
Which decade are you in and what do you LOVE most about being your current age?
Please take my poll and share in the comments below!
P.S. If you liked this article, you will LOVE my free 3-part Male to Female Makeover Course.
I pass as a cis woman and try dresses and other clothing on before purchasing and actually wearing them. I step out of the fitting cubical and look at myself in front of the full length dressing mirrors. Husband goes shopping with me sometimes and he will also tell me how something looks on me. My dresses are mostly back zip and I do wear things a woman my age would wear. I have developed natural hormone induced C cup breasts so I am not afraid of displaying a bit of cleavage and I am proud of my ‘girls’ on my chest.
I have been being female for many years and have had much practice. I have been doing this practically all my life and am now in my mid 60s. I consider myself a woman and live totally full time as a woman. I am legally married and a man’s wife. It is ‘same sex marriage’ to make it legal but we consider it a marriage between a man and a woman. I am retired from working as a male and have become a full time housewife.
Thank you for all the wonderful comments and photos, ladies! I’m amazed at how youthful and beautiful everybody looks – proving that age is only a number.
My wife of 50+ years died last summer. She was so supportive of my trans lifestyle and I feared that she being gone would necessitate my leaving my female self behind. To the contrary, I have now become a full-time woman and found a strength to face my older age with courage and joy.
Lucille is so correct in saying that those of us in later years should dress with great care and definitely a bit fashionable. I love heels and classic styles along with a lovely hair style and carefully-done makeup.
Thank you Lucille for your wonderful insights in how to be an age-appropriate woman. It has given me an inner strength to continue my journey.
Thank you for the kind words, Elizabeth. I’m very sorry to hear about your wife’s passing. That’s wonderful that you are continuing on your feminine journey.
Altho I couldn’t come ‘out of the closet’ until 4 yrs ago (at age 62), I soon went full-time after that and can dress like the 40’s look with no prob. Being almost 5′ 5″ helps me blend in too. My go-to summer attire is short-shorts and a tank top. In the photo, I’m wearing one of the first tops I ever got – and I love it.
what womens size should i wear i am 6 ft 5 inches in bear feet should i wear a large womens
Muy interesante, no me gusto, el vestir de los 50 y 60, si se tiene buen cuerpo, cintura y bonitas piernas se puede ser mas audaz, y no por mas grande mas conservador, incluso en colores, o si se es muy joven, y no se tiene pierna, no usar minifalda.
please tell me , if I ignore my age ( 50 ) to express my feminine self, dressing inappropriately
Not in appropriate – looking good gurl!
I’d appreciate tips for those of us at the lower end of the socioeconomic scale. I’m poor on account of disability (but have an M.A. degree from before), and my day-to-day life is short on “runway” or “red carpet” moments. I can only slowly build my wardrobe, mostly via Walmart [sorry] and those affordable women’s mail-order catalogs. Plus I come from the lower working class anyway, so even my cisgender schoolmates weren’t mostly dressing like the above (or the 1970s-80s equivalent!). Long story short, I guess I’m kind of an impoverished but liberated (trending-)femme 24/7 Trans Woman. Thanks!