Beginners Guide for a Mature Crossdresser

Charles was a cool grandad who stumbled upon the joys of crossdressing in his mid-60s. For ages, Charles felt like there was something missing, but he was so busy with life that he never had the time to pay it any mind. After his wife died and he retired, he now had too much time to overthink. One day, when he was out, he saw a vintage drop waist dress and bought it on a whim. It was nice to look at, so he hung it by his bedside table. The next day, he decided to try it on. That was the official start of his crossdressing. Charles was a dear friend of mine. He passed away last Christmas and I was going through our photos on my phone and kept on thinking about men who started crossdressing late in life. How many mature crossdressers are there right now? Did they have any regrets about starting so late? Are there any resources to guide them?

So, I decided to put together this guide. I hope that by the end of it, you’ll have more confidence in crossdressing in your mature age.

Crossdressing for Mature Men

Crossdressing ain’t just a young buck’s game. It can be a downright epic ride for seasoned gentlemen too. Aside from being able to present your 100%-self, crossdressing also comes with many psychological perks.

First, as you get in touch with your core self, your self-esteem will also soar. Think back to the first time you put on a nice dress and see the reflection looking back at you. This version of yourself just feels spot-on, doesn’t it? Charles described that feeling that way.

Additionally, by this time in your life, I believe you wouldn’t care much about checking societal boxes. You’ll just want to finally try the “YOLO” thing youngins are talking so much about.

You Can Crossdress at Any Age!

Again, just toss that tired old idea that crossdressing is just for the young crowd! That’s straight-up nonsense!

Age is just a number, sir. Whether you’re rolling through your 50s, cruising in your 60s, or even knocking on the big 7-0 and beyond. There’s absolutely no reason you can’t crossdress. You’ve already spent way too much time thinking about what everyone else thinks. If crossdressing lights you up, then why not do it?

The Allure of Mature Crossdressers

For me, mature crossdressers are iconic and legendary. And no, it’s not because they’re “old.” It’s because they come in the crossdressing stage with an air of elegance and wit that people can only have after going through every kind of experience.

Most, if not all, of the mature crossdressers I’ve met, don’t speak about the latest makeup trend or fashion item. I love chatting with them because they talk about meaningful things. Like their experiences when they were younger, life lessons they’ve collected, and life tips— there are many things you can learn about life in general.

There’s just something magnetic about a man who has been around the block, knows himself inside and out, and doesn’t pretend to be anyone else. These men have this slick, effortless way they draw attention. Mature crossdressers are no cheap wine— they’re Domaine de la Romanée-Conti Grand Cru 1945. Aged to perfection and priceless.

Mature Elegance and Grace

Have I puffed you up enough? Everything I said was no empty compliments too. I meant it, so know that as a mature crossdresser, you have a massive edge with all that wisdom and life experience.

Younger crossdressers? They don’t have anything on you! You don’t have to crossdress with the most trendy things. Style-wise, you’ll want to aim for that timeless, sophisticated aura. Think of those classic pieces that’ll make your natural charm just pop. You’re all about that classy, evergreen look.

But it’s not just about vintage outfits either— it’s about how you carry yourself, too. Walk tall, like you own every damn room you step into. (Here’s a tip: Know that you own a house and not many youngsters can afford that right now! Sad but true.) Let that inner confidence just radiate. When you feel good about yourself, everyone’s going to see it and feel it, too.

Tips for Mature Crossdressers

Alright, let’s get to the good stuff! Below are practical tips for all you fabulous mature crossdressers out there:

Fashion

Embrace Classic Styles

Like I said, your style keywords are “timeless,” “classic,” and “vintage.” Think blazers that give you that boss look, pencil skirts that hug you just right, and dresses that fit like they were made for you. (And can last for decades!)

Ditch the flashy, fast-fashion hype— it’s not about chasing the latest fad. You’re all about that eternal, sophisticated swag that never goes out of style.

Accessorize Wisely

You’re not new to this, during your youth days, you know how accessories can complete the whole look. I’d argue that older individuals know more about right accessorizing than youngins.

I’m thinking big pearls, brooches, thick gold bracelets, fancy hats, and monocles. I believe you have some of these in your closet, don’t you? If you do, all the better! If you’ve lost them over the years, thrift stores are practically time capsules you can dig through!

Footwear

Of course, your kicks should be on point too. But since you’re not getting younger (and that is a blessing!), always prioritize your comfort. Go for chic flats or low heels that give you that balance of style and comfort. Patent leather or Charol shoes are also dapper!

Makeup

Skincare is Key

Skin remains your canvas, despite your age. Your mature skin isn’t the same as it used to, so you need to step up your skincare. At this stage, you need to treat your routine like a hydration station— moisturize like your life depends on it! Charles used to rave about Hada Labo’s Anti-Aging Skincare line. I think it worked pretty well, considering his age and how good he looked!

Less is More

Not only because light makeup makes it easier to avoid crow feet, it’ll only save you on makeup expenses. Focus on products that make your skin glow naturally. You don’t have to perfect it.

Tinted moisturizers with SPF of at least 50 will be your holy grail — your skin needs that extra love! BB and CC creams can also do the trick. Charles loved Cathy Doll’s CC Cream Speed White. I did learn a lot from that man.

Play Up Your Eyes and Lips

Like Old Hollywood babes, play up your eyes and lips. Bold, classic red lips are always in-fashion. Soft, neutral eyeshadows are also great. Go for warm browns and gentle nudes, nothing too wild so they don’t contrast any skin folds— which by the way, is something you should be proud of, because hey, not everyone gets to your age!

A little bit of mascara to make those lashes pop is also good. But keep it smooth, no harsh lines, no clumpy products. Make it look sharp and effortless.

Realistic Silicone Products

As a mature crossdresser, use everything in your arsenal. Today, it’s easy to emulate the female silhouette with realistic silicone products. They’re also comfortable to wear, so you won’t feel anxious about adjusting a sliding padding or anything like that.

There are breast forms, hip and butt enhancements, hell you can even look pregnant if you like — the whole nine yards. The miracle of today is you can wear a full silicone bodysuit to literally step inside a woman’s body!

Issues and Overcoming Challenges

I don’t like talking about this, but there are still many difficulties a mature crossdresser would eventually get tangled in.

Crossing over into the world of fashion and self-expression will not be a walk in the park, especially for the older gents. There are a few bumps on this road, mainly dealing with what people think and accepting yourself. But hey, life has thrown you through so many other tragedies and you’ve overcome them all, right? This won’t be any different.

Look, people are always going to yap. Haters gonna hate— no matter the decade. But their opinions are just noise. Drown it out by surrounding yourself with friends and family who love you for you. Those are your ride-or-dies, the real MVPs.

If this is the case, then confidence should be your superpower. You’ve gone through things more difficult to deal with than naysayers. Remember that.

Conclusion

As promised, I delivered a no-BS guide for all you fab, mature crossdressers out there. Age is really just a number when it comes to discovering your whole self. There should be no ceiling on the joy and fulfillment you can get through crossdressing.

Embrace your true self and give zero effs about what society thinks you should be doing. The world is your damn stage! You should’ve own it way before, but there’s no time-limit to claiming your spotlight!

If this guide hit home and gave you a bit of a boost, why not spread the love? Share it with a friend or two, because we all need that tight community.