Checkmate

Dress as Though You’ve Already Arrived

Jan 23, 2025

A series inspired by The 48 Laws of Power

“Gently guide fortune and help determine the future by thinking far ahead.”

Robert Greene, The 48 Laws of Power, Law 29: Plan All the Way to the End

The word “personality” is derived from the Latin word persona, meaning “mask.” Our identities are masks we craft and present to whomever is around us, and we tweak this depending on who we see and what we want to project. In the realm of power, we must be very deliberate in what we present to the world. We have to be able to see ten moves ahead to recognize that perception shapes the reality of our future.

Personal style is one of the greatest tools we have in manifesting aspirations, projecting authority, and creating a lasting legacy. By dressing all the way to the end, you can align your current presence with the future you’re building.

Personal Style Defines Your Legacy

As discussed earlier in this series, clothing can be used as a way to visually present who you are to the world. Every powerful figure with an enduring legacy has carefully crafted their appearance to best suit their end goals and control the conversation around them. Their style becomes synonymous with who they are and what they stand for.

Iris Apfel, Kurt Cobain, Salvador Dalí, Oprah Winfrey, David Bowie

Create Your Style Dictionary

How do I want others to see me? Perception is powerful— if you don’t define who you are, you’ll risk having someone else do it for you. A great place to start is to think of specific words that describe how you want to be perceived.

For example, you could want to be seen as:

Opulent, lavish, decadent
Minimalistic, clean, understated
Effortless, relaxed, natural
Magnetic, alluring, captivating, charismatic
Edgy, bold, daring, rebellious
Playful, quirky, lighthearted

How to begin:

Think of three to five adjectives you identify with.
Now, think of your most-worn items. Are they close to what you’re imagining, or are they speaking a language you’ve outgrown? Is something missing?
Later, go stand in front of a full-length mirror. How do you see yourself now? What small thing could you do to feel closer to your descriptors? Think: Do I need an accessory, or should I remove one? Should I simplify, or am I too muted? Is this silhouette highlighting my best features? Do my shoes elevate the look, or are they too casual?

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Build Your Foundation

Once you’ve decided how you want to appear, the next move is being able to translate your vision into wardrobe. Think of this as your cornerstone: your carefully selected items that best define who you are and what you most love.

How to begin:

Research the people you admire. Find someone with style you admire and look at their wardrobes. Focus on core elements, or signature pieces. Ask yourself, what’s one piece that truly reflects who I am?
Then, start looking for it. Choose one key piece to invest in. It doesn’t need to be expensive to be an investment, it just has to elevate your sense of self.
Later, take photos of outfits you love best. See someone on the subway with a killer look? Take a photo. Loved your outfit today? Take a photo. Make an album in your phone. You can use this as reference, later, when you’re unsure of what to wear.

Visualize Your Endgame

Look from the outside, in. By viewing yourself in third-person, you can connect where you are now to where you want to go. This is not about identifying flaws and should not be used as such. This detached perspective allows you to create tangible steps to place your goal in reach.

To begin, ask yourself:

Who is one celebrity or public figure I’d be thrilled to be compared to?
How do I want others to feel when they see me—impressed, inspired, intrigued?
If my wardrobe were part of a movie, what type of character would I play?

Style is the blueprint for your endgame—the way you project yourself now can guide you toward the person you’re destined to become. Be true to yourself and never forsake your favorites. There’s a reason you love them so much—it could be the texture, the weight, the color, the feeling. Whatever it is, pull the thread. Trust me when I say that denying something you adore will only make you feel like an imposter. Your dreams will become reality the second you realize that you can be the person you want to be, now.