Don’t try to look too young for your Age

There are few things more pathetic looking than when you see an older guy obviously trying to look young. Rock stars and different artists can get away with some outside the box fashion, but if you don’t play an instrument or paint anything, it’s best to stay in the lines. I live in Orlando, Florida. Here we have a couple types of guys who dress too youthfully.

Since this is Florida, we have a surf culture spread out here and there. Surfing is a sport of mainly young kids but there are plenty of old guys who have surfed for decades and I am one of them. Older surf dudes (who actually surf) can get away with a youthful surf look. But only to a degree. A guy in his fifties can’t go to RonJons surf shop and buy anything he wants. He has to tone down his look or risk looking like he’s trying to look young.

Timeshare sales are a big thing here in Orlando. A guy with no real career can make some nice coin selling timeshares and some of these “new money” guys are characters. Making a lot of money fast in high-pressure sales produces some real doucebag dudes. Some of these guys try to cheat their age by what they do and how they dress. Most of these men are assholes, so for me, it’s both hilarious and pathetic to watch them with orange skin wearing trendy clothes designed for a guy twenty years younger and a fifty pounds lighter.


They want to attract younger women

From where I live, this is clearly the number one reason why some guys try to look and be younger. To some, being with or having much younger women is a status symbol. Guys will consider themselves more successful by having a younger girlfriend or wife and to some degree, that may have some truth to it.

The problem here is that guys will think they have to look and act around the same age as what they are attempting to attract. The reality is that they are hindering their chances with younger women by doing this.

They are holding on to their youth

For a lot of guys, their “glory days” were when they were young. Way back when they were young and carefree, they stayed up late, drank like fish, did a bunch of drugs, and fucked whoever they could. Or they played sports well with a perfect great body while eating a bunch of McDonald’s and never feeling sick or tired.

It’s hard to give those feelings up as you get older, fatter, need more money, and have a ton of responsibility. So, when being an established older man isn’t as cool for you as it was when you were young and free, you try to stay back there in youthville.

They have Peter Pan syndrome

Some boys never become men. It’s not too bad even into their early thirties with still being a boy on the inside. After that though, it can get really sad.

For some, growing up as a boy was fantastic. You had no responsibility and mommy wiped your face and made you food. You got to wake up whenever you did naturally and not have to brush your hair or your teeth. Then, when trying to be responsible didn’t jibe with your boyish vibe, mommy and daddy said “that’s OK, Tommy”, and they did the worst thing they could’ve. They enabled you to remain a boy.

They don’t know any better

An old man once told me “inside every old man, is a young man saying ‘what happened?’”. As men get older, we sometimes don’t pick up on the social and fashion cues that it’s time to act and dress older. Usually, our bodies tell us as we no longer look good in young men’s fashion. Youthful fashion typically requires a youthful body in order to look good so a belly and saggy ass makes for “no bueno” with those new style jeans.

Sometimes it takes a friend or a sister or an article like this to let you know it’s time to start acting your age.

They are getting bad advice

Using the timeshare doucebag as an example again, some older dudes get really bad advice on what to wear and how to act. Dudes that work together and have the same surfaced, lame ass goal of picking up women will sometimes feed off each other’s poor lifestyle choices. One guy starts getting spray tanned and wearing gold shoes, then he allows others to follow suit.

Also, a very young girlfriend will give social advice to her older boyfriend. So when he takes her advice, he starts dressing and acting like a man-boy. She might think it’s cute the way you walk funny in those teenage jeans and tilted Lakers lid, but to the rest of us, it looks just wrong.


Check your jeans and shoe styles

Almost all American males wear jeans. Jeans are a great check for your fashion as they do change in style and color. Most guys, as they get older, continue to buy the same style of jeans that they did when in their early twenties.

It’s not ideal to be wearing the same jeans you wore ten or twenty years ago, but that’s not bad compared to wearing ones that are too young for your age and body. Those new Diesel or True Religion jeans you just bought may have cost you two or three hundred, but that doesn’t mean they look right on your body and personality.

Shoes aren’t as big a tell with dudes trying to look too young, but they are worth mentioning. Big and bold kicks may look super cool on a rapper or teenage skateboarder, but they may look straight stupid on you. And not the good stupid. The stupid stupid.

Don’t do anything just because it’s what young people do

This is a trap some guys fall into. They find themselves doing young dude shit just to try to hold on to or relate to youth. There is absolutely nothing wrong with being contemporary and forward thinking. Just make sure that that is who you are instead of doing dumb shit just because younger people do it. And let’s face it – young people do dumb shit!

Do an occasional fashion check

Spend an hour or so on the internet checking out the fashion and style of movie and tv actors. Actors are usually at the cutting edge of fashion for their ages. They have people making sure they don’t look too young or too old in terms of what they wear and how they carry themselves.

Also, pay attention to what other guys are wearing when you go out. Find good and bad examples of guys and how they are presenting themselves in the world. Decide how you want to represent.

Be aware of what you do

The biggest mistake people make is that they don’t pay attention to how they are presenting themselves. This may sound like I’m putting too much importance on what others think, but we live in a society. You may say you don’t give a flying fuck about what anyone else thinks about you, but we all know that’s not really true.

No man is an island! Getting and being the things we want out of society greatly depends on how others perceive us. Doing a check on yourself to make sure you’re not looking like you are trying to be too young for your age may make it easier to get the things you want.


It’s perfectly ok to act much younger than what your age suggests you do. As long as you have the body and energy to do so, you’re good. I am one of those guys who hangs out with all ages and tries to do whatever interests me regardless if it seems “age appropriate” or not. That is who I am though. I’m not doing anything just to try to look or be younger.

There can be a fine line between doing things that younger guys do because you are a contemporary thinker and doer, and doing them just because you want to be and look young. The difference is that one guy is admired and respected for being a contemporary, and the other is considered pathetic. Big difference.


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