Dress Older Than You Are

This is sort of a continuation of my article from last week. In that article, I wrote about how there are some things I wish I knew about clothes that I could have implemented when I was young. That got me thinking about the general advice I would give to younger men who are early in their sartorial journey.

As I stated in my “Four Stages Of Menswear” article, many of us are pretty “settled” when it comes to how we interact with clothes. Many of us already know, more or less, what our style is and what we feel comfortable wearing. Often, that style fits into a neat little box like “ivy” or “streetwear” or “Americana” or “workwear”. Sometimes, though, it doesn’t really adhere to any one genre.

All of that is fine. This advice is not for those of us who feel like we have found our niche. What you are about to read is for the men who might be just starting out, or for those who still feel a little unsteady on their feet when it comes to menswear (at whatever age that might be).

Because the concept of clothing is so broad, it’s usually helpful to have a few little maxims to fall back on when you’re trying to hone your style. If you’re just starting out, or if you’re still pretty young, remember this…

Dress older than you are.

We men are at a bit of a disadvantage when it comes to clothes in that, for us, what’s considered “young” isn’t really well-defined the way it is for women. If a woman dresses “too young” you can immediately conjure up an image in your head of what that person is wearing. Probably something tight, short, and revealing. Something that shows off her body. Tight skirts and midriff tops come to mind.

I feel like every woman has a sense of what it means, at whatever age she is, to dress “too young”.

But men’s clothing isn’t as easily categorized. That causes men to wear the same thing at twenty and twenty-five as they did at fifteen. For many men (especially those new to menswear) clothing is just clothing. Add to that the fact that men nowadays don’t have adequate style luminaries to look up to and you’re left with large numbers of grown-ass men who don’t know how to dress to optimize their lives.

Because that’s what this is all about, right? Getting dressed is a tool for accomplishing your goals. Want to be a good dad? Want to be effective in your career? Want to find a girlfriend and get married? Want to be a respected member of your community? Your clothing choices are integral to your success in all those areas.

A good rule of thumb is to dress older than you are. When you’re a young man (in college and just out of college), what do all the guys wear? Jeans, hoodies, and sneakers. I wore the same thing at that age. If I had any inkling about wanting to dress better, I wouldn’t have known how to begin. What I should have done was dress older than I was.

What does that look like, though?

Well, if you’re at an age where all the other men around you wear jeans, hoodies, and sneakers, maybe start wearing khakis, polo shirts, and leather boots.

Maybe you’re a little older. Maybe you’ve had a career for a few years. Perhaps you even have a young wife and a child. The men your age probably show up to the office in khakis (or maybe still jeans) and button-down shirts. This is your chance to get comfortable wearing sport coats and maybe a tie once in a while.

Once you get older than that, you’re going to realize that you’ve been in the “menswear game” long enough to know what your personal style is. But that destination would have taken you much longer to arrive at without intentionally dressing older than you were at any given time.

Think of it another way: you’ll never benefit from dressing “younger” than you are.

It’s never a good look when a man dresses immaturely. Even if it doesn’t stick out as abnormal (since most of the other men dress the same way), it won’t advance your particular interests, whatever they may be. So, while dressing younger might not necessarily “hurt” you, it will never help you.

If you are always trying to dress younger than you are, you risk looking like Rick Santorum in his suit and Chuck Taylors.

Rick looks like a space alien in disguise who is trying to fit in with the other adult humans. There is just something so “off” about a mature man consciously trying to dress “younger” than he is.

And don’t let social media fool you. Those “menswear” doofuses in their fifties wearing extravagant streetwear might get a few likes on Instagram, but everyone outside of that very small community thinks they look like clowns. Social media isn’t real life. What works there doesn’t work in the real world.  

Also, take advantage of one of the many societal benefits of being a dude… namely the fact that we are considered more attractive as we age. If a man looks mature, it signals to those around him that he probably can provide and protect. Historically, those capabilities have been considered highly desirable by the opposite sex.

“What about dressing my own age?”, I hear you ask.

That’s a valid point. However, the problem with this line of thinking is that you are never your “own age”. You’re always getting older so the things you wore five or ten years ago don’t apply to you anymore! Five years might be 20% of your life. The things you wore then will look woefully juvenile for a man like you who wants to be on the fast-track to success in all areas of your life.

Here is something you’re not going to want to hear, though (and this is especially pertinent for you college-age men): if you make a conscious effort to dress older than you are, the women who are your age WILL NOT find it sexy. That’s just an uncomfortable truth. They’re going to look at you as a weirdo because they are still attracted to the immature looking men in their social sphere (since that’s how all the men they know dress, and they think it’s normal).

So, if you’re still in college and you start dressing older than you are, prepare to be shunned somewhat by the girls at the bars downtown.

Do you want to know who WILL find you attractive, though? The girls who already have their shit together. These are probably the girls who are out of school and working. They most likely have careers and goals. These girls are looking for a real man. They are the ones who are going to look at you and realize that you stand out from the pack for good reasons.

Dressing older doesn’t mean “boring”, however. There is a myriad of ways to keep things interesting, which might take the form of a western belt, a boutonniere (a real one), spectator shoes, a bow tie, an interesting watch or cufflinks, a hat of any kind, patterned trousers… the list is almost endless. Just don’t wear all that stuff at the same time.

Now, I say all this from a place of experience. When I was young, I dressed the same way as all the other guys. I didn’t think dressing well was important. I thought it was cool to dress sloppily. I thought that dressing well was feminine. I thought it was manly to not care about how I looked.

I even had this mindset when I worked my first job out of college. It was one of those corporate gigs that chews up recent college grads and spits them out. The dress code was casual so I wore my jeans and hoodies every day. I wasn’t getting promoted, but I attributed that to the workplace.

In my personal life, I also wasn’t getting many dates. I attributed that to the fact that I had no money for going out. And I had no money because I wasn’t getting promoted. And I wasn’t getting promoted because of the workplace.

I was stuck in a pretty shitty cycle of nothingness. I didn’t realize that I had a massive blind spot obscuring the one area of my life over which I had complete control that, if improved, could have put me in a much better position to succeed: my wardrobe.

I even scoffed at my voice teacher who advised me to dress well because “you never know who you’re going to meet when you step outside”. That was fantastic advice but, at the time, I thought she was nuts.

I was very poor at that point (see: crappy job) so I wouldn’t have been able to go out and buy anything new. But I did have a couple collared shirts and one or two cotton sweaters. I could have worn those with my jeans to the office for a perfectly acceptable “nice casual” look. At that age, I would have gotten the “old man” comments, which is why I chose not to wear that stuff. But I didn’t realize that it wouldn’t have mattered.

Remember, the people making those comments (or thinking those thoughts) are NOT the people who matter. They are not the people who are deciding your fate, whether it’s a boss or a potential mate. The people who matter don’t think you look like an old man. The people who matter don’t think you’re dressing “too old”. The people who matter EXPECT you to dress that way, because that’s how responsible grown-ups dress!

It was at my next job some years later when I finally discovered classic menswear and began dressing better. I wore sport coats and ties to the office with regularity. I absolutely received comments from the peanut gallery about being too formal or too old or too… something. Sure, it was a little uncomfortable at the time because I was still trying to find my sartorial footing. Every day felt like an experiment. It was a little scary!

But want to know what? I’m glad I spent those years feeling a little discomfort. Because now I feel completely comfortable in my personal style. I wouldn’t be where I am right now had I not endured those first, awkward years of trial and error in front of my coworkers who thought I dressed “too old” for my age.

Those awkward years were money in the bank for where I am now. I’m thankful for that time because now, at 40, I have (hopefully) many more years of squeezing as much enjoyment out of getting dressed every morning as possible.

So, if you’re a young man, or if you’re just starting out in your long, menswear journey, a good rule of thumb is to dress a bit older than you are. You may find that it will help you access the benefits of the men who are just above your current social or professional station.