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I believe most of the “dress for your age” rules are silly and outdated… That said, there ARE some guidelines worth keeping in mind.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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P.S. If you liked this article, you will LOVE my free 3-part Male to Female Makeover Course.
As painful as it is, at 74 years young I try to dress appropriately for my age. I do have a few “younger” outfits that I love to wear around the house and it feels so absolutely heavenly. Here are a couple of photos of an outfit that I wore to a night out at the Funky Skunk nightclub. Does it work for me?
Hi Heather! I think you look lovely! Love your dress. I’m about your age and just strive to be the woman I know I am and try to blend in wherever I am as any normal woman would. Here I am at Macy’s yesterday trying on some dresses. The sales ladies always respect me as a lady! Have fun! Suzy
Hi Suzie, thank you for your kind words. Looks like I posted the same picture twice! I meant to post one in a standing position, I will try again here.
I so admire your courage in going shopping. I wish I could do that. My wife disapproves so it makes it difficult for me. I have gone to a few support group meetings but that has mostly dried up in my area and I have gone out to a supportive nightclub a few times. And I am not into the nightlife so much at my age. I suppose I would rather go to church as Heather but finding a welcoming congregation and coupled with my wifes discomfort with Heather makes it almost impossible.
Anyway, you keep up the good work and you have fun as well.
Hugs, Heather
Hi Heather – I think you look lovely! I’m your age and just try to stay looking like the other women around me. Just be yourself and enjoy! Here I am at the mall the other day trying on some dresses! Have fun!
Hi,I’m 45,but look very young,so I feel I can get away with certain outfits,I love pastel colors,but I don’t over do it……,also,I don’t like dark colors very much. Thanxs.
Good topic of discussion.
So many times I see trans women that are in the beginning stages of transition later in life that seem to want to make up for lost time by wearing something that is not “age appropriate” (I’m guilty of that myself).
Thankfully, I have a mother that has exquisite taste that helped guide me in that area without allowing me to express myself in my own fashion.
I’m very bohemian in my everyday attire but I do dress appropriate to the event attending.
I also have a stage attire that I wear that is rock oriented since I am a rock guitarist (think Joan Jett with a splash of Stevie Nicks).
I’m in my 50’s now and I noticed in the picks above displaying the 50’s gals that they exposed their arms which is something I’m still not comfortable with while going out. My arms are a bit athletic and I don’t want to show that side of me too often as I’m actually a very soft person.
My legs are my assets so I do wear shorts in the summer with a cute top and that goes over well.
Also, I do put emphasis on my face because I do appear younger than what I actually am. I get mistaken for being in my late 30’s or early 40’s. I’m actually 55.
So mainly, I draw away from my dysphoric areas and put emphasis on my assets (legs, butt, boobs, and face).
Hi all – I’m 73 now and through out my life as a trans woman have always just tried to blend in as any normal woman would with what she wears depending on her age but ALWAYS try to stay as feminine and stylish as I can. Here is me shopping at Macy’s yesterday. Just skinny jeans and a top. Nothing outrageous. I’m always treated as just another woman doing her thing. What do you think? Thanks
Hi Suzy!!! You are beautiful!!! Love, Emily
I just turned 71 and since women unfortunately wear skirts or dresses anymore I just wear jeans or slacks when shopping and doing errands.
im not trying be flashy or too over dressed but be myself by wearing somewhere n between line’s conservative and sexy I’m age 60 now so i know not wear what younger girl’s or women wear out n public also doing my own style only starting gain too much weight round my stomach area i don’t want be out looking fat or over weight if i could shift it to other parts of my body I’d look great being short gal
Another great article with some excellent comments. I’m lucky in that I have a sister (Julie) who is 2 years younger than who knows and accepts the Christine part of me. I follow her trends as she dresses smartly and age appropriately. I keep myself in good shape and have skirts/dresses altered to fit properly rather than hanging off me. I know it can be hard but i’m so appreciative of the advice I get from the women who know me.
I’ve been “out” for over 20 years now and at 69 years old think it is more important to dress in a way that makes you feel good about the way you look. If you feel good your confidence will shine through. Think it’s also important to dress for the occasion, no a good look to go shopping in a party dress lol.