When I think of the darkest possible, most horrid places I'd never fancy being, I am drawn to the imagery of the bug trench in Peter Jackson's 2005 film, King Kong. A dark pit of immeasurable depth only allowing in enough light to let you know the horrors you are in for. Gnashing, inhuman mouths attached to every manner abomination big and small, all capable and wishing to feast upon you.
This, in no uncertain terms, is where vanity and pride place your soul. Pride will chain your soul to every impulse your fallen mind has, and it will quickly tumble down this path, which is a dead-end trip to the trap that is Vanity.
Once you come to understand that true and real beauty exists, and that it is a gift from God to be used to make His world on Earth better, your eyes are opened to all manner of possibilities and visionary ideas. However, nothing on Earth is safe from the devil. The devil will use this newfound sense of righteous beauty against you and turn it inward if you let him. It is a sneaky, careful bout of trickery that you will not notice until it has set in. You will find yourself thinking:
"I look and thus feel smarter and more capable than my fellow man, so therefore I must be!"
"Others will never reach my level of polish and dignity, therefore I am above them."
"My being beautiful, dignified and stylish affords me a degree of superiority that only I understand!"
This attitude, spoken or implied, is all too common amongst the intelligent and dignified. Its a tasty temptation, that feeling being the best dressed man in the room all too often. While nobody will be able to read it word for word off your forehead, you will carry a general sense of unapproachability about you. People will chat with you, but nobody really cares to know about you, after all, you showed up 2 dress code levels above what the invite stated, you've got it all figured out right?
Unfortunately, in my experience this trap of vanity is an inevitable obstacle in any stylish man's journey. Overdressing to events, excessive affectation, and an irresistible appreciation for one's presence before a mirror. This is the devious trap that is pride. You are better than this. Nobody is impressed and if you do not snuff this nonsense out you will drive away many people who care about you.
So, how do you stomp this vain wretch into the ground?
It's easier than you might think. Your impeccable sense of style is a gift from God, so you need to treat it as so.
Step 1: Offer it Up. When confronted with anything difficult in general, the OIU should be your first instinct. It takes training and time, but whenever you hear that "I'm better/I'm so perfect" pop into your head in any form, DO 2 THINGS IN THAT EXACT MOMENT: make the sign of The Cross, and say 3 words: "God, use this." (I learned this from Fr. Mike Schmitz) And you will find yourself easily able to chase these vain notions of self importance away.
Step 2: Find a way to serve. God does not gift us with eyes and an ability to detect and create beauty so we can hoard it all to ourselves. You find this style beautiful? You are enthralled by its dignity and beauty? You feel better seeing it, wherever it is? Of course you do! What of this beautiful world you see and love can you recreate? What element of this beauty can you use in your own creativity and create something that shares a slice of this beauty with your fellow man? Maybe it's for fun, maybe you use it to start a business and build a life around it. God will let you know.
Step 3: Step outside of your comfort zone. Yes you know a lot about your style, you are knowledgeable about aesthetics and style in general. But, who are you without your perfect outfit? Who are you dressed like a "normal person" ? If you don't brave this, you will dread it like kryptonite. If you need a planned out, coordinated outfit to command a room, then you don't deserve that room. I love my bowler hat, tall detachable collar and three piece suits, but I still pull up to the occasional bar in denim, a long sleeved polo and a leather jacket because overdressing can be a bit overrated sometimes.
Do not use your sense of style to separate yourself from your fellow man, use your gifts as a way to serve your fellow man.