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I believe most of the “dress for your age” rules are silly and outdated… That said, there ARE some guidelines worth keeping in mind.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.
What’s that? I can’t hear you over the sound of me wearing whatever the hell I want however the hell I want.
“Lynn”…You Are A Very Pretty “Girl”…That Is A Great Bra That You Have On Under Your Sexy Dress !!! Love, Paul(a)
These photos of me were taken between two weeks ago and less than three years ago. I turned 62 in July. I started to dress more age appropriately when I was 50. I was dating fairly often and was only interested in mature men my age or older. I shop mostly at consignment shops. I can buy classic designer clothing at very good prices. I have been told that I have very nice legs so I usually have the hems raised to just above the knee. I never worry about “passing”. Instead I concentrate on blending in as a well dressed mature lady. Funny thing is, now I get more compliments than ever and the gentlemen are still very interested.
i am not a crossdresser , i am a trans woman and live full time.
Dressing in order to fit in without sticking our like a green dot on a red wall is very important to me…
I avre found that what helped and is still helping is to pay attention to what is going on in the world around me as far a fashion goes.. what are the women in my area wearing? and were do they wear it?? that will really help you decide what you need etc.. Pay attention to the women around you!! study them!! and then do as they do
Lucille, about 8 months ago I posted on here for the 1st time. I was just starting my journey. You had advised me to take small steps such as gradually trim my eyebrows and put on some clear mascara. I did that and started to gain confidence when going out. From there I graduated to liner and a dark mascara. That was as far as I had gotten. I confided in a friend about my goal to transition. Well my friend blew my cover and told a number of people. That set me back until now when I finally decided to move ahead again.
So this past weekend, and using so many of your tips, I went out in public for the very 1st time wearing eye make-up, lipstick, foundation and blush, a wig and earrings and dressed wearing a padded bra, blouse, leggings and high boots. I was shaking like a leaf. I went to a gas station to fill up and a young man came over asked, “miss, can I help you?” OMG, I couldn’t believe it. I have been flying since. Of course I’m still scared to death about going out in public but you and your readers have helped my confidence sooo much.
Thanks to you and all the “girls” who write here.
Teddi
“Teddi”…As you know by now, I love to wear my Bras…Just be yourself and enjoy life !!! Love, Paul(a)
That’s wonderful! I’m very happy to hear that.
Good advice Lucille (as always). I blend best in public in large city when I’m in very average professional office attire: black pencil skirt to my knees, dark stockings, black flats, long sleeved knit top or blouse, sweater or blazer, scarf, black shoulder purse – basic bangs and maybe sides up in plastic combs/clips, ‘everyday’ make-up muted colors that blend nicely with my scarf, blouse, nails – add some elegant perfume and my sunglasses, and people see a 50-year old woman. Other casual works well here in LA: skinny jeans and over calf leather boots or Uggs, knit top, vest, sweater or jacket, scarf, shoulder purse, loose hair or up in scrunchy – very easy to blend right in and shop, walk, relax, meet friends. I take lots of notes when I’m out and see how women my age dress for workday and weekends, then do the same!!
Just wanted to make these further comments. “I don’t believe women should be worried about what is appropriate and what is not. Obviously it’s important to be aware of what flatters the mature figure and what no longer works. Style has nothing to do with age, it is understanding what flatters your body, how to accentuate your best assets and deciding what makes you feel pretty.
Whereas this has been traditional guidance and I have promoted it on Sister House, my view is changing somewhat. Here’s an interesting article from an 80 yr old fashion blogger sisterhouse.net. I have even seen 90 year olds and pleasingly plump gals wearing minis that looked good. It pretty much depends on your body shape.
The issue has always been that inappropriate dress for a TG or crossdresser depicts us in a bad image and gives rise to criticism, harrassment, and discrimination for all of us. But if you wear whatever you want within the confines of the community, no big deal. There have been times when I wish I could dress like a sissy, but not to the supermarket, although you will see it in Walmart.
So dressing appropriately also means the situation too. 50 is the new 30 and 70 is the new 40. In fact women over 60 are now becoming style icons for their ability to dress daringly but still femininely.
Overall good guidance for blending in, Lucille
Great points, Tasi. I really liked your article, as well as the blog you shared. Age appropriate does NOT have to mean boring or frumpy!! I think you nailed it in your comment above when you said:
“Obviously it’s important to be aware of what flatters the mature figure and what no longer works. Style has nothing to do with age, it is understanding what flatters your body, how to accentuate your best assets and deciding what makes you feel pretty.”
Thanks for sharing!
Hi Lucille,
Surprise. . . was always watching from the distance.
For many years now, I have been following your blogs. There are informative and interesting to read. Five months ago, I started hormone treatment.
First time, I posted my female side. A recent photo shoot finally reveals Manda. She gets alot of views on this
You’re so right about wearing the right clothes which can make one feel and look great!
Manda