The Art of the Flip: Streetwear, Vintage, and the Power of Self-Expression
By Contagion Media
From selling clothes straight off his back in crowded rooms to curating a brand rooted in culture, community, and sustainability, Austin Castillo-Leovan’s journey is the definition of street entrepreneurship done right. In this video, the founder of In Tha Cut Opportunity Shop breaks down how hip hop fashion, vintage discovery, and human connection shaped a business that goes far beyond resale. It’s a story about spotting opportunities where others see noise—and turning personal style into a platform for self-expression, environmental consciousness, and cultural dialogue. Watch as Austin shares how fashion became both his livelihood and his language.
VIDEO TRANSCRIPTION
My name is Austin Castillo-Leovan I am the owner and curator of In Tha Cut Opportunity Shop. I got started with my business from walking in the streets, being at parties, being at functions, where I would get compliments, I would get people asking me, you know, where I got my stuff from. And it got to a point, you know, I was just selling clothes in the club, right? If somebody liked what I had on, I just said, Give me 20 bucks. You can take it home. It just became something so natural for me to find and curate items. And, you know, people would be interested in them. I was able to find street entrepreneurialism and resell clothing. So it was just something that was inevitable.
I would describe the brand style as one, an element from hip hop street fashion is a big influence into what we do. What don't you love about hip hop fashion? I mean, it's a Mecca, when you think about it. You know, hip hop started in the Bronx, and from there, within 40 years, it has become an international phenomenon. Hip hop has touched every corner of the world. In addition to that, it is rooted in people being marginalized, people being excluded, outside of opportunities. And look what it has created, a beautiful culture, a beautiful art form and a beautiful fashion sense.
Photo of Austin Castillo-Leovan by KBR | Contagion Media
Second, what the masses want. You know, we want to make sure that we're giving some of the stuff that the consumers want. And in addition to that, we also like to push the boundaries of our consumers a little bit. So we want to be able to curate some items for them that particularly they may not like to wear, or may not have thought of wearing. And we kind of want to push that boundary when it comes to fashion, the type of items that we offer can go back from the 1950s all the way up to 2024 right? So it ultimately, kind of depends on what our consumers are interested in, in addition to what I may be able to find and curate on my own. And then second, it also has to deal with the style that I want to bring out during the season, some of my favorite type of pieces. Personally, I'm really big into vintage Tommy. I'm really big into vintage Ralph. Lauren. I love non branded things that have unique styles and patterns. I love things that make you stand out in the room.
The reason why I like to resale clothing as a business is the sustainable aspect of it. There's tons and tons of materials being made, shirts, pants that are going into landfills. In addition to that, all of the water that is being utilized to actually make the color of the clothing, it's a lot, right? So we want to be able to be a little more sustainable in the way that we do when you come into hip hop, and I explained about street entrepreneurialism, you learn to utilize your skills as a way to gain income. And this is one of the ways I was able to do so.
My typical day in working for In Tha Cut Opportunity Shop, one is to find the pieces. I go to different and various sources, like thrift shops. In addition to that, I may go on to like Facebook marketplace offer up. From there we take the opportunity to take pictures of the clothings, wash them, whatever they may need in preparation to sell them. From there, we go into listing and we post them on various sites like Depop, Mercari, eBay, Instagram, Facebook, marketplace. And then when we make a sale, we package, make sure we cross our T's, dot our i's, and send it out towards the end of the day, we may do a management of what we have, what we've sold, what is still being listed, and we'll make corrections and keep track of what we need to do next, for the next day, and so forth. So that's kind of like, generally, how we curate our day. For sure, fashion in my business helps me connect with other people.
Photo by KBR | Contagion Media
I mentioned this before, but fashion is an extension of who you are. In addition to that, fashion is an invitation to the community and everybody that is surrounding that community. It's an opportunity, it's a gateway, it's a conversation starter, it's an opportunity for eyes to be met, for voices to be heard, and platforms for you to utilize to speak to others. So that's how I utilize fashion within my business, to connect with others. My favorite thing about fashion is the fact that it can be an extension of who you are. You know, you're able to play around, try new things. One of the things that my father taught me when I was young is, you know, dress good, feel good, feel good, perform better, right? When you got the crisp G face I was on, or, you know, you may have a nice pair of Jordans that you keep clean, you know, nice pair of slacks and a nice shirt, whatever you prefer. It makes you feel good. And when you feel good and you have that mindset, your belief about yourself changes. And when you have that belief system built within you that makes you feel confident, that makes you feel good, your whole world can change you.
Final Thoughts
At its core, In Tha Cut Opportunity Shop isn’t just about clothes—it’s about confidence, conversation, and creating space for people to show up as themselves. Austin reminds us that fashion is more than what you wear; it’s how you move through the world, how you connect with others, and how belief in yourself can shift everything. From sustainable practices to timeless pieces that demand presence in a room, his approach proves that when you dress with intention, you don’t just look better—you feel better, perform better, and open doors you didn’t even know were there. This video isn’t just a look into a brand—it’s an invitation into a mindset.
Edited by KBR on January 27, 2026
