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The first question everyone asks when they meet me, Olga Maria, Founder of Dreams in Heels is: “How can you be in heels all day long?” The truth of the matter is that most people might think that I am only a girl who is fascinated with style, beauty and just want to always look well put together (which is not totally false). Some people even judge me or at least look at me strangely since I not only run all over NYC in my Heels, but all over Europe, South America, The Caribbean, Asia, The Middle East, across United States and Canada. I’ve ridden a bike in heels, climbed the Great Wall of China in Heels, made it to the top of the Blackcomb Mountain, to the Equator…basically, I am living my dreams in heels!


The real story behind it, which many people do not know, is that I was born with a leg condition whereby my Achilles tendon is shorter than average. I cannot walk with my feet flat on the ground, only on my tippy toes. Thus, heels are more comfortable for me. Growing up, I was mocked in school in Puerto Rico. Kids bullied me because of the way I walked. Seeking various medical assistance, I eventually had to wear boots with metal braces, even to sleep. However, even with small improvement, my gait never changed. My mother was told about a very expensive surgery, but the risks were too great, such as not being able to ever jump again, scars on my legs/feet, etc. So my family and I decided, why risk it if at that point I was already walking, dancing and learning martial arts, just in heels. After that, I just learned to live with it. I started wearing boots with heels which were more comfortable for me, even if other teenagers made fun of me. Regardless, I was always different from them. I began writing poetry at 11 years old, and preferred to read classic poetry and novels more than anything contemporary – and I rarely watched TV. Obviously, we had very little in common.

Old San Juan - Travel Blogger - Photography

In high school, it was when I started modeling that I transformed the way that I looked. As I gained more confidence, I began to sing, and learn to play el cuatro puertorriqueño (similar to a guitar but with 10 strings), which is a typical instrument from Puerto Rico, in el Convivio de Cuerdas. I started to feel, little by little, that I was following my dreams. Soon I discovered that my dreams were about exploring the world beyond my beautiful Island. A book that changed my life is The Alchemist (by my favorite writer, Paulo Coelho). This book and his words transformed the way I saw life so much, that I decided to leave Puerto Rico, my family, my home from one day to the next.

My mom and I in Old San Juan Puerto Rico

My adventure was just beginning, and it led me first to Miami where I lived for 6 months with a good friend and her family. However, it was an impromptu trip to New York City that changed my life forever. It seemed that I was meant to return to my birthplace. In New York, I started from nothing. I was here pretty much by myself; no friends or family, and I spoke no English. I only knew a few Basic English phrases and how to read them. It was very challenging for me. Eventually, I found a roommate, several jobs and enrolled in school. No one said that it was going to be easy, but all I knew was that I had found the city of my dreams – fast-paced, exciting, with people from all over the world living side-by-side.

NY state of mind


It is crazy how almost 14 years later I am still in New York, though many people thought that I would not make it here…I was just an 18 year old girl, with one suitcase, full of dreams, living in a concrete jungle. New York has been the University of my Life. I’m convinced that I have found so many opportunities here which I would not have had anywhere else. New York will always be New York. I learned that it is a tough city and only the bravest survive. And even for me, it has been a very challenging and hard place. I definitely have many stories of my various struggles, especially in the beginning. But if I could go back in time, I would make the same decisions. Everything that I have experienced in the past served as an awakening for me. From the language barrier to struggles to find work and stay in school, it all taught me something about myself, about the present and about the future. I turned each of these negative things into something positive, eventually starting my brand, Dreams in Heels.

cheers from NYC

Dreams in Heels was designed to inspire and empower women all around the world to live their lives to the fullest each and every day. I want to inspire them to be independent, adventurous, to get out of their comfort zone and to follow their dreams, while doing it all in style. After over 7+ years of experience in Public Relations and Social Media Marketing in the Fashion, Travel and Lifestyle industries, I decided to create more pathways for women to travel the world! I believe that every woman should have the opportunity to travel more, live better, connect with new people from around the globe and hopefully, make her dreams come true!

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2 thoughts on “HerStory: From Leg Braces To Heels, How This Latina Built A Career Traveling The World”

  1. Avatar

    Hi Olga Maria,

    I would love to talk to you about my Anti bully project. Together as latinas we can change the world.Best regards

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