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? Absolutely not!
I believe most of the “dress for your age” rules are silly and outdated… That said, there ARE some guidelines worth keeping in mind.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
Jazz Jennings
Josie Totah
Hunter Schafer
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.
Your 30s
30s: Transgender style inspiration
Gigi Gorgeous
MJ Rodriguez
Leyna Bloom
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.
Your 40s
40s: Transgender style inspiration
Janet Mock
Lea T
Jamie Clayton
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.
Your 50s
50s: Transgender style inspiration
Laverne Cox
Candis Cayne
Lana Wachowski
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
Alexandra Billings
Caitlyn Jenner
Tracey Norman
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!
Love,
Lucille
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Hi, I am in my 40s, half closeted and half public CD. We have occasional gatherings of CDs, Trans where there is a liberty of showing oneself. I usually wear my traditional dress which is called “Shalwar Kameez” (shirt and loose trouser). This is a full length dress comes in many colours, designs and styles. shirt can be full sleeves, half sleeves, sleeveless, it can be deep neck, low back or full neck, full back, loose or figure hugging. Shalwar also has many designs too. Also I do wear long skirts with short shirt or t-shirt. In makeup , red lipstick is must with some eye makeup. Women dresses are beautiful and their ranges and styles are limitless.
From the beginning I have always loved pretty and tastefully fem. Never slutty.Always skirts blouses pretty dresses like what I have on now,a rose floral print and of course very lacy and pretty under it all.I am so lucky at my age to have all my natural hair it is so nice to be able to do things w it.Curling irons are still a challenge.Makeup is another thing so fun just don’t overdo.Thank you and be Feminine not slutty.Kimberly!
Most of the examples were for fancy, dress up nights. I agree, that’s where you need to be wise- and remember that you’re going to be judged along with the other cis woman! 99% of the time- my outfits are for ordinary, casual times. I’m in my 60’s- and don’t give a hoot about what others are thinking- I want to feel sexy, but comfortable. When it’s a warm, or hot day- I go with what most girls wearing! That means not much!
I’m 61 and would love to meet another CD around my age that lives in or near Arkansas
Im 64
Hi
I’m 37 years old and have been a crossdresser for so many years. Just really starting to think in my life now that I’m transitioning from a crossdresser to a trans woman. And I’m accepting it each day and really just enjoying the ride of it and it makes me more happier to finally be myself. If only I could love it back more then my life would be amazing. I hate feeling trapped inside my body & home style each day just like why? I know I’m a woman deep down inside of me and that part does make me smile each day.
show more skin and be the butterfly of the party. a couple drinks and enjoy
Hi Lucille,
I always look forward to your messages, always so full of good, positive help for us. I’m on the high side of 76, been closet dressing all my life but only really have become full time over the past 3 years. I love it, I love women’s clothes, so may options, something for every mood. There’s a friendly bar/club here in town, very open and accepting to everyone, which I frequent just about every Saturday. Most weekends they have some kind of theme, and being part of the regular crowd I always try to participate. But even if there’s not, I always dress well, many times even flamboyant. I’ve gone in everything from Victorian gowns, poodle skirts with all the big, fluffy petticoasts (most of the younger people have never actually seen one), pencil skirts with the white button down blouse, fancy flair leg pants with Victorian lace high collar blouse, mini to maxi skirts, leather with thigh highs, you name it, I’ve probably worn it, even silky nighties on lingerie night. I’m particularly known for my stiletto heels, I love them, so feminine, it blows women away that I can walk around all night in 4 and 5″ stilettos, many watch for me to come in to see what I’m wearing that night, I’ve gotten many compliments about how well I put my outfits together. No, even at my age, we do not have to be frumpy. I actually think that being in a more mature group provides us with more freedom, now, it’s all about fun, we don’t have to care what others think, they don’t pay my bills. I don’t worry about “passable” never was, never will be, and even if I do begin to think about it all I have to do is go for a shopping trip to Walmart and look at many of the women walking around there, and I don’t feel bad at all. I do the best I can with what I have, and wear what suits my mood on any given day. I am prone to bright, cheerful patterns, love flowers and butterflies, clothes than feel happy. As Bobby McFerrin sings, “Don’t worry, be happy”. At our age, having survived enough close calls to compete with a cat, paid our dues, seen so many fall by the wayside, we realize that every day is a blessing. We will live this day, one way or another, how is entirely up to us. Be happy, Indeed, Life is good.
Hugs,
Jennifer
I admire you and am jealous, because I am around your age and have always wanted to be a woman. Unfortunately I have no support from my spouse or family, they say that I am just depressed about life. I want to know how to start being myself.
Thanks Rachel
I think if you still have a nice figure and face then you can still look sexy even as an older trans woman. I’m 50 now but I still like to show off my figure, that’s the best part of me, so if I covered it all up then more attention would be drawn to my face, which is the hardest part of my body to keep young looking. I agree that outfits need to be more tasteful as we get older, but always show off your best assets ladies, your age is just a number. ❤️
Hi Rachel, thanx for your comment. Yes you have lovely legs, so definitely show them off, if you’ve got it, flaunt it as the saying goes.
Have fun
Liked your comment and so agree. Anything to take focus off the “bad” parts. Still have a pretty killer bod so I tend to show off legs and/or stomach area. There I get the confidence needed to then not worry about other parts so much and have a good time every time.