Be Someone Else’s Source Of Confidence
Are there clothing items you can think of that you really WANT to wear, but don’t because they are a little outside your comfort zone?
Maybe it’s something a bit more formal than you usually wear. Maybe it’s something that doesn’t really fit with your current style. It could be more “ivy” or more “workwear” or more “punk” or more “whatever” than you’re used to.
Maybe it’s a hat, or a pair of boots, or a boutonniere.
When we step out of our comfort zones a little bit, don’t we always kind of secretly hope we will see someone else wearing something similar as us? It certainly helps give us confidence to see someone similarly dressed. We don’t feel like we are the lone weirdo.
That’s totally normal. Humans are always looking for tribes to belong to and we always want to “fit in” with each other.
No matter where you are in your sartorial journey, we all have our “stretch” items. These are the things that are a little bit outside our normal wheelhouse.
If you normally wear jeans and t-shirts, then your stretch items might be khaki pants and a sweater.
If you normally wear khakis and a sweater, your stretch items might be a blazer and tie.
If you normally wear a blazer and tie, your stretch items might be a full suit and fedora.
If you normally wear a full suit and fedora, your stretch items might be jeans and a t-shirt.
Whenever we take the plunge and step out in our stretch items, we feel a twinge of uncertainty at first. I know I do. However, I always feel a little more confident when I see someone else dressed similarly.
Then it dawned on me.
I should be that person!
In other words, I should be the person from whom others draw their confidence in what they hope to wear but haven’t yet gathered up the courage.
I wrote last week that I always wear my boater hat on July 4th. No one else wears one and that’s fine with me. But I hope that other men see me wearing mine and think “Huh, maybe I could wear one someday too!”
I have only seen one other person wearing a boater in the wild. It was actually a fairly young man walking through Grand Central Terminal during rush hour. He had an otherwise simple outfit consisting of an OCBD and chinos. This guy definitely wasn’t a dandy. I think he just wanted to wear a boater.
I always think back to that guy when I wear my own boater and it gives me a little shot of confidence to wear mine.
You know that old saying “be the change you want to see in the world”? Well, be the person who gives others confidence. Be the person whom others look to when they need the courage to wear cool stuff. And you can only do that by wearing cool stuff yourself!
Wear the leather jacket, or the fedora, or the bow tie and you will stick in the minds of other men when they feel unsure about whether or not they can really reach their own style potential. They’ll think back to the time they saw the cool guy (you!) wearing a tweed jacket around town and gather the courage to level up their appearance.
Don’t, for the rest of your life, be one of the many who need someone ELSE to give them “permission” to wear the things that make them happy. Don’t wait around for others to be braver than you.
As I’ve said before, this isn’t a dress rehearsal. You don’t get another shot at life to wear the cool stuff once you get used to it.
Be the mentor for others. Be the one others look up to.
Because there are men out there who WANT to dress differently or “better” or just want to try out something new, but are nervous about looking weird. The knowledge that those men are out there, quietly gaining confidence from looking at what you’re wearing, should give you your own confidence boost!
Other men will see you and think, “Oh wow! I wish I could wear that!”
You’ll likely never know how many men you inspire to dress better as you go about your day, and that’s ok. But just know that you’re helping men grow into their best and happiest selves simply by what you pull on in the morning.
