When I was six years old my entire extended family on my mom’s side took a collective trip to Disney World. Looking back, the only real memory I have from the experience is being so tired and jet lagged that one of my brothers and I fell asleep face first in our personal-pan pizzas from Pizza hut. If only cell phones and their attendant cameras had been around then, right?

While I don’t have any permanent moments from the trip, other members of my extended family all have varying things. One family in particular had hand-drawn caricatures in their hallway for years. They were the kind seen fairly often at carnivals and amusement parks. The artist did a quick sketch that got the basic proportions of each person correct and then over exaggerated one or more of their key features. If the person’s face wasn’t unique enough, then the artist would typically insert a drawing of them performing their favorite activity.

Obviously in the correct context, these things can be a lot of fun. We may be self-conscious about our long necks, large noses, or odd face shape, but when we see it depicted so well and so cartoonishly, we can’t help but relax our self image a bit.

However, in the wrong setting, an over pronunciation of any attribute can serve as a distraction. I’ll give you an example from my own recent experience.

I’ve had a beard off and on (mostly on) since 2007. I look like I’m 15 without it and it helps to define a non-existing jaw line for me. I’m lucky enough to have a full beard that comes in evenly and well. Up until last October, I’ve always worn it short and well-trimmed. I worked in a more corporate environment and never really had the inclination to allow it to grow past the horrible itchy phase. But, for some reason this last fall I decided I wanted to grow it out.

At first no one really took notice. The change was subtle enough that it had to get pretty long to catch on. However, after a month’s worth of growth beyond my usual trimming, it started to get a lot of positive comments and reinforcement. I posted this picture on Facebook:

quite a few old friends came out of the woodwork to tell me they liked my beard. At that point I enjoyed the compliments almost as much as I enjoyed the underhanded comments I’d get from my mother (it doesn’t matter how old I get, I still love getting a reaction out of her). I was past the point where it itched, and it became something I was comfortable with. I enjoyed the contrast of a full beard against the sharp lines of my haircut. It was a good mix of Rugged into my normally Refined and Rakish aesthetic.

So I just let it keep going. It got long enough that I started to need to shampoo and condition it, use a beard oil (review coming soon), and even have my barber trim it and give it shape for me when he cut my hair.

It got so long and curly that I started to look like Cthulhu. At one point the responses from people changed. I became the beard guy and it completely overshadowed everything else about me. It started to affect my relationship with clients at work, friends and family, and even casual acquaintances. Don’t get me wrong, it’s not like people started to talk down to me or criticize me. What they did do was start seeing me as just a beard. It became a topic of conversation every time I spoke with someone I hadn’t seen in more than a week. It was a distraction for other people and an overbearing character trait for me.

I had become a living, breathing version of the caricatures done at Disney World. The rest of who I was had started to turn into a simple back drop for my beard.

This isn’t to say there’s anything objectively wrong with a long, full beard. Nor is there anything wrong with pushing the envelope of a man’s own comfort zone and that of those around him. The breaking point for me was when it became the most dominant part of who I was to most people beyond my close family and friends. I was the “beard guy.”

In the past I’ve written about how to dress when a man wants to be the focus of attention and how to dress when he wants his clothing to be the main draw. My beard had taken me so far into the latter camp that it didn’t matter what else I did in the former. I could wear a solid suit, white shirt, dark tie, and dark shoes to a funeral, in a fit and cut that didn’t look extremely fashion-forward nor outdated, and I’d still just be the “beard guy” to everyone else who was there.

It’s not just beards that create this effect. It can be tattoos, jewelry, loud clothing, always wearing the same colored shirt, or any number of good concepts taken to excess.

As men start to dress better it’s easy to get caught up in the enthusiasm of doing so. It’s an area so vague and unfamiliar to many of us that the positive responses we get from people become addicting. As a result, it becomes easier and easier to seek that high by always trying to step up our game to the next level – and that’s what creates the world of high fashion and trendiness. The end goal shifts from being well-dressed to being unique enough to get attention – and, while there’s room for that at the right place and the right time, it shouldn’t be a constant display from any man.

If you’re looking for a brand that can represent the fact that you’re a man who shapes the world in his image, I suggest giving Alfred Dunhill a try. From bags, to tailored suits, from stationary, to simple support of men who act deliberately, their products and lifestyle help tell the world you’ve arrived.

No I didn’t watch them, although I do own a TV and even spend some time watching it each week. However, my Twitter and Tumblr feeds blew up with this stuff all night Sunday and into the day Monday.

Whether we like to admit it or not, these men are at the peak of society. Men want to be them and women want to be with them. They have fame, fortune, and influence – all of which are indicative of a level of power. Yet even these apex men and their reputation are impacted by their appearance. Obviously some of it is fueled by a bottom-up mentality, in which people not as high up the social ladder will grab onto any apparent flaw or weakness in an attempt to level the playing field. But it’s not just fueled by jealousy, those who worship these celebrities look at their clothing as well. It’s a way to confirm that they really are as cool, put-together, and flawless as hoped for.

So here are the top things I learned from seeing all of the photos of the men at this year’s award  ceremony.

Pay Attention to the Break

Whether it’s one of many things going wrong with a look, or the only problem to ruin perfection, pants that have too much break is a near omni-present issue at celebrity-attended black tie events. I get that not all of these guys are style gurus who care, but they are dressed by professionals who should know better. It’s getting to the point that I’m starting to think it’s a subtle way of indicating elite status in an occult group. That way people like me can write about how bad it looks but really they’re just signaling to each other that they’ve sold out their souls.

Standing Out Can Be Overrated

In the past I’ve written about the difference between dressing so people notice the man and dressing so people notice the clothes. When someone is at the social level these men are, the only reason a man should want people paying attention to his clothing, rather than paying attention to him, is when he’s trying to avoid recognition. Although there is the occasional trend setter, most guys who attempt to out-unique others just come across as lesser men trying to status-jockey within their own group.

If who the man is carries more social capital than his implied willingness to expose himself to risk by standing out, it’s better to emphasize the former over the latter.

As a counter point to this argument, all of the attention-seeking outfits shown thus far (excluding Pharrell) are within a normal enough range of tradition as to be considered classic. Therefore, by choosing to embrace a little risk these men communicate that they don’t take themselves too seriously and enjoy dressing up for its own sake. Although Leto’s hair looks ridiculous, everything else about his wardrobe was spot on, making the cream dinner jacket a good tweak instead of a cry for help.

Proportion is Key

The three men who were the best dressed all had their proportions down to a science. Pant length, lapel width, button stance, and more are all in complete agreement with the natural build of each man.

If DiCaprio and Levitt were to swap tuxes, they’d both look ridiculous, even if they were tailored to fit their bodies. What makes their individual appearances so strong is how well all of the minor details compliment their unique features.

What it really comes down to is, the higher a man climbs, the more he’s scrutinized for any apparent flaws. I could do this same post about a high-school band’s banquet with even worse offenses but no one would care. However, the mere fact that these are celebrities means they’re constantly under public scrutiny. If a man wants to maintain a hard-earned image of dignity, daring, respect, rebellion, or anything else, his style needs to be consistent as his reputation increases.

Of the many trends and fashion statements happening currently, these are the worst. Not all are equally offensive, nor are they equally popular. However, they’ve popped up often enough online, in shows, and on the street that they’re starting to become regular and should be avoided.

Pants Tucked Into Boots

This is probably the most tempting for a lot of men because it’s also the most common. However, rather than appearing more rugged and badass, it makes them look dainty and girlish. At its least offensive it looks like this:

And at its most, it looks like this:

Man Tights

Much less common but still seen often enough in high-fashion areas to be worth calling out. This shouldn’t even need to be explained.

Overly Large Lapel Pins

I’m a fan of a little ornamentation on the lapel. But it needs to be kept in check. This is most commonly seen on guys in wedding parties, but is starting to transition more and more into everyday clothing.

Drop-Crotch Pants

Mostly worn by musicians and other celebrities, ultimately they end up looking like this:

Extremely Deep V-Necks

I love a good V but this is taking things too far. It doesn’t matter if you’re well-built like the guy above or scrawny:

Or if you have a hairy chest instead of a clean one:

There is nothing masculine about deep cleavage.

These an other trends will wax and wane in popularity. The trick is paying attention to overall impression given and avoiding those that are either too far removed from tradition or evoke an image that’s too feminine.

Last night my wife and I were out to dinner when we got to talking about a few people we know and their appearances. Reading that sentence I realize it sounds gossipy but we were focusing more on why they look the way they do, rather than just poking fun at them.

There are a few women we know who have spent time with my wife shopping, getting their hair done, learning how to do makeup, etc. They ultimately fall back to no makeup, hair in a ponytail, and jeans and a T-shirt. The same goes for some men in our lives. They’re guys I’ve done full, albeit unofficial, consultations with who, after a month or two, still end up coming back to dad jeans and Seinfeld sneakers.

It’s funny because they’ve invested their time, energy, and money into buying pieces for a new wardrobe and yet end up defaulting back to what they know and are familiar with.

We are all creatures of comfort and habit. Whether we’re miserable, happy, enslaved, productive, healthy, or dying, it’s easier for us to remain in our current situation than it is to improve our lot in life.

The easiest and most glaring example of this is in regards to health. Every year people resolve to get in better shape, lose weight, eat less junk, and feel better about themselves.  I have one relative who is suffering from a myriad of “diseases” simply because she treats her body like a garbage disposal and won’t exert any discipline over her diet.

We’re all guilty of it. I was trying to lose belly fat for five years before I really took it seriously enough to make any real progress. Instead it was easy enough to justify where I was because I wasn’t really fat, I had more important things to do with my time than count calories, and my wife still thought I was attractive so it didn’t matter anyway -pretty easy and common rationalizations.

Part of it is that we trick ourselves into believing that half-hearted efforts are a legitimate attempt at improving ourselves. We get the high of feeling and projecting our discipline without really needing to have any self control. We can tell people we’re watching our diet, but if the belly’s still there after three years, are we?

So bringing this back to style, we can get caught up in aesthetic inertia as much as anything else. A man may buy a great pair of chukkas, but still throw on his sneakers. He does it because he’s used to his sneakers and they’re already broken in. Or because the chukkas were more expensive and he doesn’t want them to just be common, every-day shoes. Or because he subconsciously realizes that people will perceive him differently and he doesn’t want the increased responsibility that comes with increased respect. Whatever the reason may be, dressing well is not an easy thing – even after paying the money for the clothing to do so.

It’s not nearly as difficult as exercising, eating better, approaching a girl at a bar, or learning to better control our emotions, but it does still take some mental discipline and fortitude. In our heads it should be just as easy to throw on that pair of chukkas as it is to lace up the old New Balances, but it’s not. We have too much value invested in our appearance to be able to make a change without the effort of discipline.

I’ll say that again for the back row – All men invest enough value in their appearance that making any change will require mental discipline. Even those who claim their style doesn’t matter are really just esteeming themselves as someone who doesn’t care about style. By getting them to admit that they do, their whole paradigm has shifted.

I’ll give you an example from my own life. I’ve worn a shirt and tie, mostly with a suit, almost every day for the last ten years. It’s part of my uniform and I’m just as comfortable in that as I am in my casual clothing. However, one thing I’ve never really spent much time wearing is workout clothing. Even when I was active as a teenager, I wasn’t involved in traditional sports. So gym shorts, sweat-slicking shirts, and gym shoes were a foreign concept for me up until this past year. In fact, when I first started going to the gym, I was wearing Chuck Taylors, old running shorts, and my normal T-shirts.

Once I got proper exercise clothing, I loved wearing it to the gym. I felt a difference in the way I was able lift and work out. It didn’t make me stronger or better, but it did make me more comfortable. That being said, I was self conscious if I had to go anywhere else in my workout clothes. Swinging by the grocery store or stopping off at the bank was uncomfortable for me because I still identify as someone who dresses up. When I stand in line waiting to check out in my running hoodie and cross trainers, I look like half of the other men in the store – and that’s a foreign feeling. My own lack of discipline wanted me to make the ridiculous decision of going home and changing before being seen anywhere besides the gym in my workout gear.

Silly right? Well thankfully it requires less self control than other aspects of self improvement. One of the easiest steps a man can make is to throw out or give away his old clothing. There’s no temptation to put on that baggy, ironic band shirt when it’s sitting in a bin at GoodWill. Just like eating healthier is easier when there’s not junk food in the house, dressing better is easier when the slob uniform has been thrown away.

Much like developing any other good habits, dressing better requires less mental effort the more often it’s done. It’s further proof that learning to do so is an easy investment in improving a man’s life. Once he’s taken the necessary weeks to acclimate to dressing intentionally, it becomes second nature – meaning his will power and discipline can be used on other, more trying improvements.