Alex Winston Turns Her Opera Background into a Killer Pop Career

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Alex wears Coach X Gary Baseman Buster Le Fauve Handknit Crew.

Decked out in Stuart Vevers’s spring collection for Coach, singer Alex Winston opens up about pop, New York, and an unexpected background in opera.

The world of pop music seems to be inhabited by teenyboppers making international stardom more a matter of nepotism or highly funded image than honest work. Singers like Alex Winston are a rare discovery, not only in the sophistication and cognitively engaging nature of her work, but also her honesty regarding the difficulties of trying to make it in perhaps the most finely beautified of music genres. Her first album, 2012’s King Con, seems to be belatedly garnering the attention it deserved, with journalists repeatedly mentioning how improperly unrecognized the work went upon release.

The talk of King Con comes mostly from excitement over Winston’s still-untitled sophomore album, which is due out in July. We talked to the excited pop darling as she finished a series of noteworthy shows at Austin’s SXSW, touching on how she started singing, opening up on the second album, and what she learned throughout the years. BlackBook shot the up-and-comer wearing pieces from designer Stuart Vevers’ spring collection for Coach, cheeky Gary Baseman collaboration items among them.

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Alex wears Coach X Gary Baseman Buster Le Fauve Leather Jacket

When you’re not out on the road, where are you based?

I don’t currently have an apartment but I’m based in New York. I’m subletting. I’ve been there for five years. I grew up in Detroit and did music there as well but I had an opportunity in New York and I sort of said “screw it,” and moved and kind of didn’t look back, and things started picking up right when I moved and it’s been great.

What’s your experience of New York been like? A lot of artists seem to have a love/hate relationship with the city.

Yeah, it is an artist-friendly city but it also isn’t at the same time. People don’t sit and talk about how much their rent is like it’s the weather for no reason. It’s difficult, it’s not an easy city to live in, but it’s a great city if you can pull it off. Like I’m sitting with one of my bandmates right now and they have to hustle all the time just to make music in the city and play in different bands and different shows to make a living. I’m really fortunate that I started doing this professionally right when I moved there and I’ve been able to keep busy with it.

When you were younger, you were involved in opera. How did that come about?

Well, I think I started doing it because my mom didn’t know what to do with me. I was singing around the house, driving her fucking insane, and she had a friend that taught opera that she grew up with and she just put me in singing lessons with her. I did that from the time I was ten until I was 20. And I liked it fine, you know, but I was out of place there. It wasn’t my choice. I wasn’t like, “Mom, I love opera music so much, I want to do this as a profession.”

But it was good for me vocally to stay healthy and to learn how to actually sing, but then I feel like when I started doing my own thing I kind of had to unlearn a lot of that, because it was all very…you’re pretty much reading what’s on paper and trying to sound like something else, and that wasn’t me…The things that I find interesting are flaws and being able to have your own voice and not be pristine and perfect, and just show a bit of realness.

How does your new music differ from previous work? 

Well, this record’s a lot different from the first record in terms of lyrical content and concepts. The first one was totally about other people, completely, and sort of like fantastical stories about things I had memories about, like weird niche subcultures and things that I found interesting. It was stuff that I liked so I was writing about it, but this record was solely a personal record, and it was about the past two years of my life. So it was very different, and very weird for me to write about myself.

Also, the second record is such a weird headfuck too because you understand the process and what’s going to happen. But I think at a certain point you have to detach from that and not worry about it and not worry about being vulnerable and putting yourself out there, because at the end of the day, it’s the most important that you make something really honest as opposed to [worrying about] what other people are going to think of it. But at first it was hard for me to wrap my head around. It was like, “Do I really want to say this? Do I want people to know that this is how I felt?” But now I don’t care. I’m too lazy now.

You sound like you’re a lot more confident now than maybe on the first album.

I was reading something that was like, “Experience comes from failure.” And it’s true! It’s like, it’s the hard shit that you that makes you a pro. The way you understand how a business works is by going through the ringer and through all the crappy stuff.

What’s the biggest lesson that you’ve learned or advice you could share?

I think it’s like, learning to know what you’re willing to do and what you’re not willing to do, and also when it’s appropriate to compromise. Like those are some of the biggest things that I’ve learned throughout this; sticking to your guns creatively but also being willing to embrace things that aren’t as comfortable at first, because ultimately it hurts your career. When I was younger, I was so stubborn with everything. And now I’m learning that sometimes compromising is okay, as long as it’s not compromising yourself artistically. But there are so many aspects of being a musician these days. It’s not just about the music; it’s about things like social media, and it doesn’t come naturally to me.

Musicians are now expected to do a lot more than just make music.

It’s stupid and it’s unfortunate too for people that are just musicians. I mean that’s the thing too…people have tried to pigeonhole me into bullshit that I don’t want to do. Like, “What’s your thing? What’s your thing?” Well my thing is making songs that hopefully people will like. But it’s easier said than done. It makes other people’s jobs easier when I guess you have something that’s really marketable.

How did you become certain that you wanted to be a professional performer?

I mean, it’s the only thing I do. I’ve always known I was going to be a musician. I didn’t have anything else. I barely graduated high school. I was working on music back then. I don’t have another thing. This is just what I do so I do it because I have to do it. I love making music. And to have a career where I can just continue to tour and play shows for the next 15, 20 years — that would be my dream. I don’t have to be a megastar. But to be able to have a career, I want to be a career artist, so that’s what I’m working towards.

What type of people do you think is connecting with your music?

I honestly don’t know! It’s kind of diverse. When I go overseas it’s like 40-year-old men. Sometimes young teenage girls or like fun gay guys…I don’t know! It’s just all over the place. And I like that. It’s not like a specific niche, I don’t think. Like I haven’t been able to figure out my demographic yet, which I like.

What are your thoughts on live performance?

I love playing. It’s my favorite part. I love performing and my band is amazing. They’ve been with me, some of them, since I moved to New York. And so we know each other really well. To be a solo artist in New York without a consistent band is really hard, and I’m so lucky to have them, because like I said earlier, everyone’s trying to hustle and make money to make a living, and they have to do what they have to do, but my band is super dedicated. They’re talented and it’s just fun. We have the best time on the road.

Do you ever get tired of life on the road?

Honestly, I like it. I don’t like being in one place for very long. Like, that’s why right now I don’t have an apartment. I’m between New York, L.A., and Detroit…and London. I like living out of a suitcase. I don’t like sitting still. So for now, I still really like it. Ask me in a couple years.

What would you like to say to fans before they press play on the new album?

I guess just know that it’s really personal, and the most honest I will ever be is on this record. And I guess I just want them to know the process and that it took a lot of work, a lot of work to get me into a place where I felt comfortable sharing myself, and I hope that people can relate to some of the things that I’ve been through. I hope maybe it will help someone else out if they’re going through a tough time.

Alex Winston photographed by Rodolfo Martinez for BlackBook.  Styled by Alyssa Shapiro. Hair and makeup by Ashley Rebecca.
Alex wears Coach X Gary Baseman Buster Le Fauve Leather Jacket and B
uster Le Fauve Handknit Crew.

The Fashion We Loved from 2014: The Year’s Top 10 Moments

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Start the countdown…

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10. Weather wise, this men’s sweater story shot by Rémi Lamandé still feels apropos.
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9. Consider new ways to wear an all-time favorite: denim. Photos by Jaesung Lee.
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8. Ben Rosenzweig captured social media heartthrob Jessey Stevens in the coolest leather looks.
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7. Cozy up with the warmest winter outerwear, shot by Adeline Mai at The Ludlow in NYC.
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6. 2014 was the year of athleisure, and Justin Bridges shot a few street-ready looks you can wear to the gym.justinbridgesdknyportrait1

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5. We love a pop of electric blue. Ben Rosenzweig captures the boldest fur accessories of the early fall.
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4. The Fifth Harmony girls have incredible, adorable style. See their exclusive photos for BlackBook, shot by Justin Bridges.
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3. Glitter in the daylight? Hell yeah. Rodolfo Martinez shoots the sequins to wear before the sun goes down.
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2. It’s the middle of winter, so we’re looking at Logan Jackson’s depictions of the brightest, hottest summer beauty to warm up.
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1. Jaesung Lee captured all the best spring 2015 beauty — our favorite look, right this way.
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Shine On: 24 Hours of Casual Bling

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Edythe (Marilyn) wears a sequined tank top by H&M, jeans and sneakers by Acne. Photo by Rodolfo Martinez for BlackBook.

Just because the sun starts to set earlier now doesn’t mean the season has to take sequins down with it — in fact, we might all be better off with a little extra shine in its place. You might automatically think “evening” when spotting embroidered, beaded, or sequined pieces, but our favorite time to bust these items out is when it’s least expected — right smack in the middle of the day.

Ground those extra special pieces with über-comfy shapes like boyfriend jeans, sweatshirt silhouettes, and sneakers. It’s the ultimate relaxed glamour.

Click on the images below to see photos full screen

Edythe girls up Acne boyfriend jeans and a men’s tee with a fitted, embellished jacket by H&M.

A relaxed sweatshirt shape pairs beautifully with an embellished and ladylike pencil skirt. Both from H&M.

Photographer: Rodolfo Martinez
Fashion Editor: Alyssa Shapiro
Makeup: Ayindé Castro
Hair: Hikaru Hirano

Check out more of Rodolfo Martinez’s photos for BlackBook here.

(We Are) Seeing Red: How to Wear It Right Now

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Edythe (Marilyn) wears easy cutoff shorts, a red dress as a slouchy tee, and leather jacket with red details, all by Diesel. Photographed by Rodolfo Martinez.

Red splashed up all over the pre fall collections, from Thakoon to Opening Ceremony, Proenza Schouler, Moschino, Michael Kors, MSGM…

Classics like leather jackets, cutoff shorts, tees, and sweatshirts all make up a weekend wardrobe’s foundation. These easy to wear and simple pieces work wonders, especially come Saturday. Once you’ve got that part down, the question is how to turn it up a notch, without adding any hint of fuss. Our answer? Red.

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Edythe, cozy in a roomy hoodie, still manages to show off her legs in this red hot leather mini skirt. All by Diesel.

Add a punch of red into an easy weekend foundation of black and attract just enough attention — as much as you’d want running between the dry cleaners, Whole Foods, and drinks in the Biergarten. Grounding an intense shade with leather, cotton, and denim will help you sink right into the weekend, even if it will draw extra eyes your way.

Photographer: Rodolfo Martinez
Fashion Editor: Alyssa Shapiro
Hair: Hikaru Hirano
Makeup: Ayindé Castro

Click here and here to see more of Rodolfo Martinez’s photos for Blackbook