It’s Kind of a Funny Story: Samantha and Matthew Orley

Learn how the two designers met and formed a company together


This “episode” of It’s Kind of a Funny Story is a little different. Meet Matthew and Samantha Orley, a married couple who founded their eponymous label with Matthew’s brother, Alex Orley. Because the three have been a trio for so long in life and business, it only seemed fitting that the “how we met” story would be told not just by our usual two participants, but all three members of team Orley.

Leandra Medine: So how did you guys meet?

Matthew Orley: Well, Alex and I were born in the same household. We share parents and two older siblings.

Samantha Orley: And all three of us met as summer camp.

Alex Orley: I was friends with Sam before I was friends with Matt. And that’s true still.

S: So we all met at this camp that we’ve been going to since we were each 7 years old. Their grandparents actually met at the same camp. Half the kids are from Detroit and half are from Toronto where I am from. So I’ve known Matt since he was 7 and Alex probably before that.

L: Were you friends at camp?

S: Well I was older so…

M: As friendly as you are with anyone that just so happens to be there when you are as a kid.

S: We were friends.

L: And you’re the same age?

S: No, I’m a year older.

L: Ok! You’re a puma!

L: So when did you guys start dating? When we were 18 and 19.

S: We were going to be counselors.

L: And what was that initial conversation like?

M: Dating? There was a lot of prodding by various relatives on both sides of our families.

L: So your families knew each other?

S: Oh yeah, very well before we were even born.

M: Our aunts and uncles are friends with each other – there were various friendships there. Our grandparents knew each other.

S: We both have very big families that are characters in themselves. Our families would even be on vacation at the same place and spending time with each other.

M: There’s a lot of overlap.

S: That predates us.

M: With Sam and I, there was definitely encouragement on both sides of our families.

L: So you started dating at camp when you were 18? Did you go over to her and say like, “Hey, I’d like to give you a kiss?” because you can’t really date in camp. Or ask her out – where are you going to take her, the canteen?

M: We did go to the canteen.

A: You guys probably didn’t start dating until after camp.

S: No but we hooked up at camp.

L: This is actually pretty impressive because when you start dating someone at camp, it’s usually under the guise that summer will end. Like, “I’m going to lower my standards for the summer because I’m only around you hoodlums.”

S: But I think there’s a comfort when you’re at camp. And then I guess it just continued. It was before Matt’s freshman year of college.

M: We were visiting each other and going back and forth.

L: You were in Canada and you were in Detroit?

M: I started college in Ann Arbor and Sam was at college in London.

S: It’s only a two-hour drive.

L: So not London the city…

M: Ha, no, London in Canada. It’s a very close drive and we saw each other very often. There were about two years of us going back and forth on weekends and I think that there was this weird state of limbo where we really liked each other but we were in different places and there was a lot going on for both of us individually. And then we decided to go abroad together. Sam was going to Paris for her senior year, and I don’t know if that’s more traditional to go abroad in your senior year…

S: Not that many people go abroad. And at my school it was harder to go a semester abroad than it was a year. I knew before we even started dating that I was going to go for a year.

M: I was going to do a junior year semester, which is somewhat typical, and I decided to go to Paris and Sam was already there.

L: So you guys consummated your romance in Paris.

S: That was the first time we lived in the same place. Alex came to visit us, we had like a little apartment, and he slept on the futon.

L: So you guys lived together when you were there.

M: At first when I got there Sam was living with a host family. As soon as I got there she started staying over with me and the family got very upset and said like, “You have to either have all your meals with us or you have to move out. We signed up for you to be with us and keep us company.” They were an old couple that signed up for the program for the company.

S: They would call me asking me where I was. I was like, twenty-one and my mom hadn’t been doing that since I was thirteen.

M: So Sam was like, “Well, I’m moving out.” She moved into my like NYU apartment that they had given me. I think most of the kids lived together but I’d requested a place on my own and I got this amazing place just by luck. We ended up living together for that semester. Alex came and spent two days with us. Alex was in his freshman year at NYU and flew from New York to visit us.

S: And then I was graduating and had decided to move to New York because I had a ton of cousins and family here and while we were in Paris, Matt transferred to NYU. So we essentially moved to New York at the same time, and he moved in with Alex. And that’s sort of when Orley really started.


L: Became an idea?

S: Yes, because Alex and I had actually worked together for a minute because I started working at Helmut Lang and Alex was also working in fashion. That’s when we started talking about eventually doing something, the three of us.

L: So you married her because you wanted it to be named Orley?

M: That’s basically…

S: We started before we were even engaged.

M: But it felt like it would work out if there was that marriage.

S: And now everyone thinks were siblings.

A: Or people think we’re married, which my girlfriend loves.

S: We only got married last summer.

L: How long did you date?

Matt and Sam in unison: Ten years.

L: Ten years and you never broke up?

M: I mean, there were a couple of minutes, but nothing serious enough to include in the larger history. Would you consider the time that you and Abie split?

L: Yes, we were broken up for three years.

M: But it was like a minute.

L: No, it was a very very tumultuous three years that ripped my heart out of my body and then like, hit a jack hammer over it.

S: I’d say for us it was pretty continuous. When we were broken up, nobody other than the two of us knew about it.

M: And when I think about it — the first couple of years when I was at Michigan – it could have gone either way. Then when we were in Paris together it sort of just solidified it.

L: So how has marriage changed your relationship?

A: It’s really affected me the most.

S: I don’t think anything really has changed since we’ve been married aside from the name, which has made it a lot easier.

M: Yeah, the dynamic existed between the three of us before we were married. It was still somewhat of an unusual coupling.

L: What about specifically between the two of you? You don’t feel a little bit more comfortable even because you’re actually married now as opposed to just dating?

M: Yeah I think so.

S: Yeah I like being married. I like being an Orley.

L: And you’ve now been married a year and a half?

S: Yeah, well a year and a little bit.

L: Do you find that entering the second year is different than it was the first year?

S: No, I don’t know. We’ve been together for so long that it doesn’t feel like, “Oh we’ve been married for a year.” It feels like we’ve been together for eleven years, if that makes sense.

L: I thought that I loved being married for the first year, and then I entered the second year and I was like, “This is fucking awesome!” It’s so much better, I don’t know why. Or I thought I loved it for the first year and then I entered the second year and I was like, “This is where it’s at.”

M: I guess it’s changed a little, but once you’re past that point and you’re just settled into it, it’s really nice.

S: I think if anything it makes us more solidified as a couple. With Alex though, he’s now my brother-in-law. That is now more defined.

L: When did you launch Orley?

M: January 2012.

L: So you were not married yet?

S: We were engaged.

M: We weren’t married until August 2014.

S: Did we get engaged a year later?

M: February 2013, and then married August 2014.

L: How’s everything going with the company?

A: Really good, very busy. A lot of deals. A lot of moving parts. Went on from doing two collections a year in 2014 to five in 2015. So it’s a little tiring.

L: Do you find that’s too much?

S: Well, we’re doing three women’s and two men’s collections.

M: So much is still exploring what works at our size. And I think we’re still trying to figure out the best way to be a men’s and women’s brand while still being relatively small. And trying to grow but that it’s smart growth. Trying to figure out how to support ourselves in the areas in which we need help. So it’s a lot to process.

A: I would say the output isn’t challenging, it’s the calendar that’s a little tricky because working with Italian factories, they close in the month of August and that’s essentially our busiest month.

S: I feel like you adapt – I’m sure it’s the same for you. I sometimes think, “What did we do with our time when we were doing two collections?” And maybe because there was less of us we were doing more, or maybe you just get better at doing everything. I feel like you adapt.

L: What have you found to be the most challenging part of working together? Or I guess, before then, how did you decide to work together?

M: I don’t know. I think we all felt like there was a common interest in doing this and we all felt we brought different strengths to the table. And what we could accomplish together might be stronger and faster than if we were setting out individually. The fact that we were all different people and still are and bring different skill sets plays a big part in why maybe we enjoy working together and feel comfortable doing so in spite of the relationship of brother and wife and sister-in-law that exists.

A: Right. I think it’s sort of being tired of working for other people and then all of us having our own background that we brought to the table that allowed us to start, if that makes sense.

L: What was the conversation like when you were like, alright, let’s do this?

A: I remember it being…not formal, but a very established meeting. Like, “Meeting one, bring your notebooks. This is the first meeting of the new company.”

L: Did you think that it might affect your relationship?

Everyone: I don’t think we were thinking about that a lot…

S: But I’d say it was an adjustment for Matt and I at first. You go from spending weekends and evenings together to literally all of your time together.

A: They had full time jobs the first six months that we were working, maybe longer. But we were also working out of their apartment. So I would go to their apartment every day.

M: That was tough in the beginning because I still had a full-time job, but Alex would come to my apartment every day at like, 9:00 A.M. And it almost felt like it was my apartment, but it wasn’t.

A: Right, that was difficult.

M: You adapt to all the situations that you put yourself in because you have to know yourself to know what is best for you and what works for you. And as you grow and your company grows, you have to make decisions that will keep you mentally healthy, so you are constantly re-evaluating what those things are and how you can be better.

A: Our early fights would be Matthew saying, “Don’t do that, you’re in my apartment,” and me saying, “Well, I’m in my office so don’t tell me what to do.”

L: You are also brothers, so it’s probably hard to take orders from one another.

S: I think that’s actually a more difficult dynamic than the husband and wife one.

M: What’s your hourly rate, Leandra?


L: I missed my calling, huh? Sam, do you find that you get between it sometimes?

S: I’d say that I’m very, if anything, very even-handed. I am not taking Matt’s side just because he’s my husband and that’s probably what was hard at first, that I am a partner to both.

L: To these two brothers, and one of them is your husband. And you were at one of their high school graduations, which bonds people for life.

M: It’s true.

A: It makes it better though, that’s the way I see it. I think if Sam had come in later on and been in a partner who was very new to the relationship it would have made it very hard for her to understand it. I think the fact that she’s been around since we were all kids makes it easier for her to know the nuances of things.

L: What have you found to be the most taxing part of working together on your martial relationship?

M: Separating work and home.

S: Yea, but we’re pretty good about it.

S: We sort of have rules, like we don’t bring computers home from the office.

L: So you don’t have computers at home?

M: Nope, never.

S: Because obviously you can check an email here and there from your phone, but it is so much harder to do real work.

M: That has been such an amazing thing to have in place and live by, because it has kept our sanity so much.

S: And if you actually need to do something, you go into the office, because that’s your workspace and home is your home space. But also, we were together for so long before we worked together that we have a relationship that exists outside of work.

L: So that’s been the thing that’s keeping you sane as a couple?

S: Yes.

M: I think so.

A: Having an office has been great.

S: For all of us, I think that was important.

L: Okay, I think that’s really good advice: don’t bring the computers home, even if just for your own sanity.

M: I can go further than that. I don’t even like to have my phone in the bedroom. We don’t have cable TV. I think that helps a lot.

A: Those are all just little incremental things that, once you get past the new computers at home makes the difference.

L: Do you find that you invariably end up talking about work though?

All: No.

S: I mean, something comes up once in awhile, but not usually. Also, it helps because any conversation that we would be having that’s important would involve Alex…

A: Which makes it public. The idea is to make it public and not have conversations that are happening one on one with anyone.

S: Any conversation we would have we would probably want to include Alex.

L: What are your favorite things about each other?

A: You guys both say your favorite things about me first and then you can say your favorite things about each other.

M: I think Alex is very driven and very…

A: Oh I was kidding, but thank you.

M: I admire in both of them the differences in personalities in traits and skills that they bring to us that I lack.

A: I think we’re all pretty different. That’s why it works.

S: I am trying to think of the one thing that sums us up. With Matt, I feel like sometimes it’s scary that we can literally read each other’s minds. We are very much the same person in terms of our relationship and life.

M: I think Sam’s extremely driven as well, and she’s very caring.

S: He makes me laugh. I am probably the only one who laughs at all of Matt’s jokes.

A: I will back that up.

M: There is no one else who appreciates my humor.

L: Well, what initially attracted you guys to each other? What pushed you to be like, “Okay fine, meet me at the canteen.”

S: I think it was a total thing where it felt so comfortable, like it was meant to be. We were just hanging out, it felt right.

L: What I find really interesting, the common denominator in all of these conversations, is this level of easy-ness. The right relationship always feels really easy, and I experienced that in my own situation when we got back together. Which is that you don’t have to think twice, you never wonder what they’re doing, where they are. It almost feels uncomfortably easy, because it’s like, “Am I supposed to feel like I’m related to this person?”

M: It’s important that you have someone who wants to grow, someone who you can see that you can grow with, and that you can change together. It’s funny, we were with Rob Fishman yesterday, and Rob and Sam and I were talking about high school friends. And I said, actually I think the only person who I still hang out with who I knew from high school is Sam.

I think that speaks to the point that we’ve both changed a lot as people but we’ve recognized that we want to change with each other and help each other and we’ve very much grown as people. It’s a really important part.

L: Yea, that’s a very good point. When my husband and I got back together, for the first two or three months that we were together I was like, “Am I regressing? Is this me going back to a comfortable place instead of charging forward? Is this what my future holds, that I have to hold on to what I’ve already known?” I’m so glad I was wrong.

M: I probably will not be the same as I am now in five years or ten years, and I recognize that Alex won’t be either, and Sam won’t be either. But if we decide that we’re going to evolve together, that’s a big part of a relationship.

S: You learn how the other people think or work, or more about their work personalities and how you work with them.

L: That’s really interesting. But your circumstance is pretty unique. You met really young, you’ve known each other, essentially, forever. And you never really broke up. Did you ever wonder if there was anything else out there?

M: Never.

S: No.

A: I wonder all the time.


S: But I think it gets back to that comfort thing, you know. It’s crazy, like wow, we’ve been together eleven years. That feels like ages. But then it also feels like no time at all.

L: What kind of advice would give to your single friends?

A: Get married as fast as you can.

S: Well, not everyone is as lucky…

M: True. But I also think there’s a culture in New York amongst people our age, in this urban fast paced environment, where people are always looking for the next best thing. It is a culture encouraged by all the dating apps, you’re constantly moving forward and you can’t really settle. And if you can pull yourself away from that and recognize everything that’s good with what you have going on it will make you a lot more satisfied.

That’s it, that’s all I got. But that’s really good advice. Just step back and assess what’s good for you and appreciate it.

L: Sam, what sort of advice do you give to your single friends?

S: It’s funny, I’ve noticed that most people I know, once they meet someone they really connect with there isn’t any bullshit. It’s very quick and they’re moving in together in weeks or months. So I don’t know, I don’t really have any advice. I didn’t have to deal with any of that.

L: So let’s say I was single and I was really upset about a guy and I was like, “I just need your help, I’m so bummed, you seem to really have it figured out. 11 years…what should I do? Talk me off the ledge.”

S: You can’t give yourself so much pressure, you can’t think about it too much. I’m a big believer in “if it’s meant to be, it’s meant to be.”

Photographed by Krista Anna Lewis


Get more Postmodern Love ?