Main Street: First Twelve

Mia Risher

Dillon Milardo by Ginger Hutchinson

Dillon Milardo by Ginger Hutchinson

There is a small clothing shop in the back of Main Street Market. A leisure and sportswear boutique, every inch of First Twelve is packed with new and vintage designer pieces. Everything from Chanel sweaters to soccer jerseys fill the space; stacks of Gucci crew necks are piled on the tables, and Adidas shoes hang from the ceiling. The store also carries clothing created by owner and designer, Dillon Milardo. On February 9th, I walked down to Main Street to talk to Milardo about the creation of First Twelve.

Despite his seemingly wild time at Mezzo Grille the previous night, Milardo was talkative and engaging. Throughout our conversation, he became increasingly energetic as he reminisced about the challenges and opportunities of the past that helped him open his own storefront and online shop.

During our hour-long conversation, four different people came in to the store to chat with Milardo, including a Wesleyan student and one of his family members. It became clear that Milardo is part of the community here in Middletown, an undeniable contributing factor to the store’s success. We begin the interview talking about Milardo’s time growing up in Middletown and what led him to open First Twelve. Lastly, we discussed how proximity to Wesleyan University has played a role in his journey.  

Below is a transcript of our conversation.

What is your name and where are you from?

My name is Dillon Milardo and I am from Middletown, Connecticut.

So, you have lived in Middletown your whole life?

My entire life. Born and raised.
What did you want to be when you were growing up? Was clothing always a passion of yours?

In my younger years, it was, to be honest, to be a professional baseball player. I was definitely obsessed with baseball. I had a passion for it. I mean this was before the age of 13, so this was early. Clothes and fashion were always a passion of mine as well. But I thought I would be more of an athlete. I was always an artist but I was obsessed with baseball.

What was your first job?

My first job was working at an Italian deli. It was here in Middletown. It was on South Main Street called The South Side Market. And I absolutely hated it. My uncle got me the job and I was their dishwasher. I don’t think that I lasted more than two months there because I just couldn’t do it anymore. And actually from that point forward I was like “I don’t know if I am cut out for this.” Because I saw all my friends doing jobs like that at that age and it just seemed normal. I couldn't last at any job. I just wanted to do my own thing.

It seems like that job had an influential impact in your path from towards First Twelve.

It hit me that I am not normal as far as working. Because I was watching all the other kids my age go about it just fine. I mean obviously they didn't want to be there either but they lasted probably two or three years. They were consistent. Me, I was just like, “I can't do it.” Then I went to another job. It was at laser tag. There was a laser tag on Main Street. It’s closed now. And I lasted like two or three months. Not because I got fired or anything, I just had to switch. I had to change what I was doing at all times.

Was your family supportive of these changes?

They were like, “what's wrong with you?” They just couldn't figure out why I couldn't stay at one place. They were in a way supportive. And every single time I said “I am just going to do art. I will paint more pictures. And I can sell and make more money than I am making here.” I was kind of doing that in a sense but I was young and they still encouraged me to work since that was what all my peers were doing. They didn't want me to be the odd man out. Even though I knew that I would be fine.

When did you fully embrace the arts and painting? What was the first thing in did in the more artistic direction?

So, the artistic side was all on my own. I never worked somewhere. I just started painting a lot on  my own. It was not even in school. I was selling paintings on Etsy and on another website. It would take a long time to sell on those sites. Oil or acrylic paintings. A lot of landscape or cityscape type stuff.

Do you have a favorite painter or were you influenced by any painter?

Um, probably like [Edward] Hopper. I like painting cities but into or out of a window. There had got to be a window. That’s what I was hooked on.

Were you going to New York City?

Yeah. I was taking a lot of pictures there. Yeah, most of the paintings I made were of New York. At the time I was going [to New York] all the time.

And how did this transition to clothing? Was there a first piece of clothing that you owned that you were particularly proud of and really loved?

Yeah, a soccer jersey. It was A.C. Milan (an Italian soccer team). I actually got it at their soccer game. They were playing at Gillette Stadium. I bought it there. That’s when I started liking soccer jerseys and making it a style. I started buying a bunch. [This was when] I was in high school. Probably 13 or 14 years old.
I went to hear about the process of transitioning into a store and opening up this space. What was your role? Walk me through the process.

I started at the LLC. So we didn't have a store for a couple years and we were just doing it through online sales. I was working a city job in the summertime when I came home from college. Once again, I felt pretty disconnected from that. My parents got me that job. Anyways, during my time working there I was also designing. All day I would be on the website that I made or trying to sell things on Instagram. So I was at this job but I still was doing business. And before I knew it my mind was completely tuned out of that job and that life. I was selling to friends mostly. I also sold online to people I don’t know. But then what happened was that we got featured on Complex. Then we just started getting a bunch of sales.

Woah, that is really cool. Complex is a really influential platform. How did that happen?

We weren’t even doing anything interesting. I was making stuff that looked like soccer jerseys but not for a team. Believe it or not, at the time, there wasn't anything like that. It is common now but at the time I was like “it would be so cool to make something that looked like a soccer jersey.” But we didn’t even reach out to them. I googled the name and there was an article. So some writer just did an article without asking. He just wrote about his own perception of us. He actually writes for Vogue now. He is pretty up there... So that’s what happened. We weren’t even making crazy money. But when I did the figures I was just like there is no reason for me to work at another job. I didn’t even want to go to school. But that was pushing it I couldn't break it to my parents. This was my senior year. We were doing well. Major stores were carrying us. VFILES in New York City. Revive near Detroit. And a random store in Hong Kong. I knew the idea of finishing school was good but I didn't care. That whole last semester I would wake up, drive up to the school, and not go to class.

Where were you at school?

I went to CCSU. I was an art major. I didn’t even go to the art classes. I did my own art at night. I just wanted to do my own thing. So I would drive by the school and go to Starbucks.

Did your family know?

No! They saw there was a lot of progress. They weren't happy… but when I broke it down to them they didn’t even check my grades. I lucked out. They ended up being supportive in the end.

When you were opening this, were you alone? I know I just met Kiwi, was he involved?

No, he came in later. He was still in Harlem then. I am the only owner. But all my friends helped me out. They were very supportive.

How did you find this location?

I used to go to the Emporium all the time to go on my laptop. We weren’t going to open a store for so long. That’s something you do when you are old. But I would walk through the mall everyday and wonder how much these spaces were. So I made a call and it was kind of reasonable. So, to be honest, we just took a leap of faith. This was three and a half years ago.

How long had you been selling at this point?

Only a year and a half or two years. So this was all super quick. If I was to see this as an outsider I would think it was too rushed. But you kind of just got to do it. Make it work. Even if you don't have enough money.

Did you want to be in New York or were you happy in Middletown?

I was kind of looking at apartments in New York. But then I thought it might ruin things. I would be paying a lot of rent. The gain could be there but who knows. But then I got the store here. My initial plan was to keep the store but then grow. So I could still go to the city eventually. I would just need someone to manage this store.

Is there a big customer base here?

Yes, just because I am from here. There are lots of high schools and there is Wesleyan. Middletown is big and connected and diverse. But people here are not big shoppers or fashion forward. So the foot traffic isn't that much. If I was in NYC or LA it would be different. But [Middletown] is surprisingly good for what it is. You kind of just have to build it up. Online we connect to people outside of Connecticut. But I think opening in Connecticut was a good idea.

Did you make any big mistakes during this process?

Everything was a mistake. I messed up with everything. There wasn't one thing I didn't mess up on. Just not knowing how to do anything retail or business wise. I didn't know how to take orders or whatever. I didn’t know anything about business. So it really was all on the fly. I bought a book about business and I read it. But I didn’t absorb it.

Was there any family member or mentor that helped?

Nope. My parents checked to see how things were going but I kid you not there was no mentor. I don't know if I wish there was. It seems like people have those. But I don't know. I have never been somebody to look for that. I do everything my own time and my own way.

How would you describe the type of clothing you make? It is like street style but more athletic?

Yeah, I like the street style look. Definitely a casual, classic, sportswear look. But more of a modern twist. You got POLO which is a classic American look. But they are lacking in the modern twist or European flare. So that’s the angle I try to come at. It is all stuff I like to wear.

Streetwear is a newer, emerging form of clothing. What is its place in the fashion industry? What drew you to it?

It is wearable. There is so much of it. You can express yourself with it. It is not a cookie-cutter look. People want to express themselves now and to be bold.

Do you follow any designers / do you have a favorite brand now?

Stone Island.

Stone Island is pretty cool. It has recently become more popular I think. But it’s more overseas. It’s not as popular here. But a lot of influencers in England love it.

Definitely, Stone Island is more European. They are all over England. We get a lot of this stuff from there. It’s usually second hand since it was a popular look for people’s dads and uncles. I was drawn to it because it looks sporty but casual. They add that flare or that patch. They experiment and are super innovative. They don’t think to just slab a logo on it. It doesn't even need a logo.

It is cool to be surrounded by all this cool clothing. Do you have a favorite part of working here? Or a least favorite part?

I actually don't really like working at the store. Lately I am trying to train people and I want to be designing and taking care of business. I really want to focus on designing. That’s what carries the brand. I have been selling other brands since I was like 11 or 12. I wasn't even allowed to have an ebay account but I used my mom’s name.

How do you get the pieces that you sell?

Thrift stores, my old clothes, or gifts. I was always thinking “I could sell that.” I didn't want to work a real job so the motivation was there. I was not cut out for a job so I was like “how can I make money?” So I started selling clothes. When I opened the store, I didn’t even think about putting it together. But then it hit me. If I put everything together and made it a boutique it could work. It was the Wesleyan kids that made me do it. They would come in and I would see what they would be wearing. I knew they would love buying this stuff.

[A friend comes in and disrupts the conversation]

How do you know him? From high school here in town? How have you built up your community here at the store?

No, in high school I felt disconnected from everyone. I knew I was different and didn't know what it meant. I didn't know if it was a good thing or a bad thing. Later on I realized it was a good thing. When I got to college it hit me that all this time it was a good thing. After college I only stayed in touch with my roommate who co-founded this and with a couple of other kids I kind of talked to. But it’s more people I met randomly. I am only around people I feel comfortable with. But almost every person in my friend group I met randomly. You can meet someone at an art show or at a party. And then you think, “that kid might play a role in this.” There was a time I would just go to New Haven to Starbucks and I would meet someone. Those situations you just randomly meet people. It is less forced. And Wesleyan kids. After I opened this store I met this kid name Rick. He was this kid from Hawaii who has now graduated. He came in and was taking pictures with a film camera. We got some cool pictures. He was super outgoing so we just did it. He then brought like four or five kids here. They turned out to be pretty well known people that do a lot of cool things. So it spread like that. It made an impact. We posted those pictures everywhere. Everyone knew their faces. Upcoming and current Wesleyan kids knew these kids.

Was that happening all on Instagram? What role was social media played in this?

Social media played a big role. I don’t know how I would do anything without it. How would you even advertise anything? A billboard? A magazine? Social media is the only way. Everything about every brand is on there. Even the biggest ones. And I don't see those big brands doing much else other than Instagram. Maybe a TV commercial but not really.

Yeah, it’s all about Instagram and influencers.

Literally that is all it is. Yep, social media is the way to do it.

[A Wesleyan student comes in and disrupts the conversation]

You seem to know a lot of Wesleyan people. I know you said you go to bar night and to campus parties sometimes. Do you have any fun Wesleyan stories?

Post Malone. It was a spring music festival. It was put on by a kid who was a dance major. He was really involved in the arts and with event planning. I met him when he came into my store a few times. Finally he asked me to help him sponsor an event for the fashion side. It sounded awesome. He said they were trying to book an artist. Somebody from Post Malone’s high school went to Wesleyan. He wasn’t close to him but enough to make it happen. But no one knew [Post] at all.

When was this in Post’s career? Had White Iverson come out?

It was buzzing on SoundCloud but he wasn't known. So no one was too pumped but it was still a cool thing to do. So we were like, “let’s do it!” So they booked him for a couple thousand bucks. Super cheap. That day came. Post Malone went to one of the houses at Wesleyan. We were all chilling. Nowadays if I was going to see Post Malone I would be super hype but at the time it was just a casual thing. So we went inside and he was with his girlfriend… I think they are still together. And his producer was there. I actually still keep in touch with him. His name is First so we made a connection since I have First Twelve. We exchanged numbers. I also exchanged numbers with Post Malone but he changed his. But this guy never changed his number. We still keep in touch. So that night was insane. He was supposed to go perform at a reasonable hour but we were in that house just drinking and partying until midnight. So it was no longer an outdoor event. So they had to do a quick switch to one of the big halls…

Movement? Psi U? Eclectic?

Yes, Eclectic. So they moved the concert there at 12:30. I think he had four songs total. The original ones. There was maybe like 50 people. It was exciting but I promise you no one knew him. But it was good music. And at the time we actually gave him a bunch of merchandise. It probably wasn’t his size since he wears his shirts big. The other guy maybe wore some of it. But if Post wore it it would have been cool.

[A friend comes in and disrupts the conversation]

Everyone at Wesleyan has their own style. You can tell people are from everywhere. It’s pretty cool. My school was a state university. Nothing of the sorts. No individual look. I liked to dress different. I wore a lot of Kappa.

Actually, during my first months at Wesleyan I came in here and saw a pair of Kappa tracksuit pants and didn’t really know what they were. I thought they were cool. And then I did some research and soon everyone was wearing them. So you kind of introduced me to Kappa.

I am not kidding I wore Kappa in 2010. I never saw anyone else wearing it in Connecticut. I saw it because an Italian soccer team had it as their sponsor. No one knew what it was... but I thought it was sick. So I ordered it from their actual website. It was all in Italian. There were no stores carrying it. It didn't catch on until a couple of years ago. And I actually don't wear it much now. The jacket I had was hard to find but now they make it every season. So I sold it. But I wore it to death.

Yeah and now it's at Urban and all those stores. What do you think of Urban Outfitters and Pacsun?

I never shop there but I go inside to peruse and see what they are doing. It’s bad. It’s fashionable but there's nothing unique. It is made to be sold. It has everything next to each other. This goes with that. It is cookie cutter. If you took some piece out of the store and put it on a blank wall it could be dope. But everything about it… the whole set-up and model just throws me off.

Do you have any trend predictions for 2019?

I always predict trends. My friend has this software because we worked in NYC. So he has the login info to this software that says the trend. It tells you what the trend will be it. It is an exact forecast. It is crazy. It is how stores stay ahead and on top of things. But I just think of trends based on what I want to wear. I will just start liking something. I don’t really know why. Right now I feel like this summer is going to be sort of... preppy. Lots of yacht club and sailing. Like a nautical look. People will be wearing brighter colors. I never check Hypebeast because I don’t like to see something like that and get influenced. I like to go off of what I am thinking. I have been hooked on sailing for the past six months. I have been loving it and obsessed by it. So I went onto Hypebeast the other day and there were three brands that had the title “yacht club inspiration for SS19.” I was like “woah.”

Okay, we are almost done. Do you have a goal for 2019?

2019 I want to be a globally known brand. More influencers. I have networked enough where I have a plan. There will be influencers to push the brand.

[Milardo’s cousin comes in and disrupts the conversation]

You could probably find Wesleyan students to help. Do you have anything you want to say to the Wesleyan community since you have this platform right now?

Thank you. The Wesleyan community has really influenced my thoughts and ideas. You guys come from everywhere so you bring a little piece of everywhere to Middletown. It makes Middletown cool.

Thank you. My final question is: who in Middletown should I go talk to next?

Ford News Diner. The owner named Kay. That is a cool place. They are a staple.

We want to hear who you’d like to meet next. Contact Mia Risher ( or Ginger Hutchinson ( if you’d like to make a suggestion or get involved in the making of the series.