How to Dress to Conquer the World

Help for the days when you’ve lost a little bit of your sparkle.

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Photo Credit: Artificial Photography

I was wearing my favorite dress. 

White polka dots against black tulle, T-shirt knotted over top, black lace choker, and boots that made me feel invincible. I was walking to class, and a girl came up on my left. For some reason she kept going straight, almost as if she were trying to walk through my shoulder. 

Right before she ran into me she stopped, then said – lips pursed, staring at my dress – “Are you…serious? It’s Monday.”

I’ve been on the receiving end of comments like this often, because every day, I enjoy taking the time to “curate” and present my best self to the world. It’s my way of waking up and embracing the challenges of the day. But sometimes people misread this as arrogant. Some people think I’m trying too hard. Which means the situation above isn’t a unique occurrence. 

I’ve heard stories from friends and family who dress to face their day and conquer the world, and who are shamed or looked down upon because of it. (It’s something we’ve talked about on CF before.) On college campuses (and in the wider world), that strive so desperately for diversity, why are we sitting on the voice of the individual?

When did embracing who you are and who you want to be become a bad thing?

I can’t pretend to have all the answers, but I’ve been living from a place of trial and error for the past five or six years, so I thought I’d share a piece of my story, and my advice for conquering such identity crises.

First, think of your clothing as the voice that speaks before you can. 

It’s a vehicle, one that carries you through classrooms and coffee houses and various social settings. Like it or not, it says something about you. It doesn’t have to say “trendsetter.” It simply has to say “You.”

In the words of Coco Chanel: 

“Beauty begins the moment you decide to be yourself.”

DISCLAIMER: You might not be into fashion, and that’s fine. You also might not care to be into fashion, and that’s also fine. You can be fully, 100% you without fitting into what the world considers “fashionable.”

Photo Credit: Syd Wachs via 

So, how do you find your “voice?”

The first step is to recognize and seek out things that resonate with you. These things can be simple – a force of nature, a person walking down the street wearing an amazing jacket, a moment in a conversation, or a word on a page. Take note of what moves you. When you begin to understand what compels and interests you, you can begin to find ways to incorporate it into the way you dress.

The second step is silencing your inner critic. There will always be a voice inside your head saying, you can’t do that. You can’t wear that. You don’t have a right to wear that. Listen to it and you’ll discover which lies you have been buying into. 

(Hint: pay attention to what goes through your head the next time you get dressed). 

Learn to break free from those negative voices. This is not so much a step as it is a process. I struggle every day with embracing the person I want to be. When I’m feeling insecure about an article of clothing, an accessory, or a way I’m presenting myself, I ask: Will NOT wearing this make me feel like I’ve compromised who I am? Will I regret not wearing this today? And, by not wearing this, am I losing a chance to be 100% myself, 100% (or at least, close) confident and mentally prepared for today? 

“Conformity is the only real fashion crime. To not dress like yourself and to sublimate your spirit to some kind of group identity is succumbing to fashion fascism.” — Simon Doonan

Find similar questions that will cause you to think, and ask yourself those when you’re second-guessing yourself.

Photo Credit: Jazmin Quaynor

The third – and final – step is understanding that life, fashion, and identity looks different for everyone. 

There will be naysayers. People will misunderstand you. People will judge you. People will put you in a box with nasty labels – labels that might be freak or diva or punk or trendsetter. On the days when you feel like screaming because you don’t live in a box, remember that you live in a beautiful part of the universe that’s yours, undefined by a word. Remember that you have been created with a unique voice and purpose. 

To silence that voice out of fear would be to devalue one of the single greatest gifts you can embrace as a human being.

So, go out into the world today and be yourself.

Have you been judged and criticized for your style? 

Are you all about style empowerment, or following fast fashion trends? What’s your favorite item of clothing, that makes you feel “yourself” when you wear it?  

5 thoughts on “How to Dress to Conquer the World”

  1. People need to stop judging what others wear for whatever reason. Thanks for the positive and inspiring post 🙂

  2. I was starting to think I was the only one who had encounters with the “Ugh, It’s Monday” girls. For the longest time I didn’t even realize I had this reputation at school and at work as the clothes horse. I will never understand why people think it’s okay to gossip about and criticize others for actions that have zero impact on them. It’s not like I’m stealing everyone’s lunches. My life is boring enough, I refuse to spend it stuck wearing some khaki norm-core prison uniform.

  3. This is fantastic! And I totally agree with Chloe on the “treat yo’self” mentality! (ps: I wanna see the outfit you described at the very beginning–it sounds fantastic!!)

  4. I actually felt this today because I like to dress nice as a sort of ‘Treat Yourself’ thing, and I felt so awkward because everyone else was in such casual clothing! Thanks for posting this?


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