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I believe most of the “dress for your age” rules are silly and outdated… That said, there ARE some guidelines worth keeping in mind.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.
I’ve strived for age an age-appropriate appearance through my 50’s and 60’s and generally feel comfortable with that look. Lately, however, I’m more and more interested in a bit more flashy even sexier look with shorter and tighter dresses and pants as well. I’ve worked hard to keep my body slimmer and curvier and just want to recapture my “unspent” youth. I have a sense that my notions are more popular with the 70’s group than some people think. I’d love to know if I’m not alone in this desire.
Nancy
Dear Nancy,
I just spilled over into my 70’s and have the same feelings.
Unfortunately, I’m now having old age health issues and my body is beginning to sprawl out, while I already look like a linebacker in drag being 6-3, 270, 52 inch chest and size 16W shoes.
But, I still feel pretty most of the time. Guess all we can do is work a little harder at looking our best and shooting for a look no more than 5-10 years younger.
Leather and Lace Dreams,
Ms Luna Marie
You know, Luna Marie, you look so naturally feminine in your photo. Your relaxed and confident look is something I’m going to have to work on too. Spilling into 70’s was difficult for me but I’m adjusting slowly as you seem to have done.
Nancy
I’m 57 and overweight so I wear loose fitting clothes and I only wear flats. I’m married but I’m bi-sexual so I like lingerie. My wife and I are the same size so I wear alot of her clothes. I love dressing as a woman it makes me feel sensual
I don’t necessarily agree you have to “dress your age”. I’m in my early 50’s but get mistaken for being in my late 30’s pretty often, and I love that. Age is a state of mind, so why get shoehorned into an old adage that you have to “dress appropriately”. Wear what you like if it makes you feel good. There are appropriate, and inappropriate, ways to dress at every age. So if you can pull off that slinkier outfit, I say go for it!
In public one wants to at least come close to one’s age.In private,I think it does not matter all the time.You can have fantasies going back a few years reliving the feminine experience at different ages.As we get older it is nice to relive the younger years.Of course one does want to use the information at this site to get the details down to really feel the many joys of the feminine experience.It is great to perfect the many facets of feminity by continuing to learn and educate oneself.True joy.True bliss.True self awareness.And peaceful contentment to wherever one falls on there feminine side and journey.Thankyou Lucille and staff for the understanding,kindness, education etc as many improve their feminine ways because of your dedication.
I agree with Trish, Susan does not look as good as she usually does ,the color and cut does not do her well. But , have always admired her acting ability and looks. I also think your right about your own build, also how you feel in what you wear, Tasi you look great I would not have guessed you were in your 70’s from your picture, more like late 50’s . I’m 67 and dress more like a late 40’s gal, very small 140 lbs 5 feet 9 . Also like Cheryl, enjoy 3to 5 inch heels, it also helps my skating muscles.
I just turned 60 but I certainly don’t feel like it and hope that I look younger than my years. I try to dress age appropriately with clothes that accent my figure without revealing too much. Most of the time I wear nice tops with a pair of jeans or capris. For an evening out it’s a conservative top with a skirt or slacks. I’ve invested in good shoes and a designer hand bag but I try to purchase them when they’re on sale. I’m nearly 6′ so I favor pumps with 3″ heels or flats. Like most ladies I’m all about comfort too. I wear Chaco sandals, L.L. Bean moccasins, Birkenstocks or a pair of Vans. I don’t have a lot of jewelry but what I so have is nice.
Lucille,
Excellent post and very important. I am a 54 year old trans women and although I miss the fun short skirts of my youth, its so important to dress your age especially for women. Important thing us girls need to know is that you can still feel and look feminine with clothes in any age group like you mentioned. I went to trans event and I do not like to judge but said…really? The benefit of being an older trans women is that we can merge easier with other genetic women. As we get older our hair is going to turn shades of gray, if you wear a wig then it has to match nature. – Bless you all and happy holidays – Charlotte
Charlotte, I could not agree with you more. I am a 69 year old closet trans, as my career requires me to be the male exterior. I have been a girl inside since I can remember, maybe 3 or so. At this point in life, I am happy that I have real breasts (grown, not implanted, and a 38 B+) and I feel so sensual with them. When I can dress as who I really am, I am so happy. Unfortunately, I cannot pass, without a significant investment in plastic surgery on my face. Life and family commitments have kept Debbie inside, but she is alive and well. I commend you and others who are fortunate enough to really take the big step out. Bless you all.
Good Advise.