The Most Stylish
Bostonians 2015

Presented by Simon Malls

Jean Wang

  • Age
  • Occupation
    Marketing manager, M.Gemi; blogger,
  • Residence
You recently made the move from a job in finance to fashion. What’s your new role?

I’m on the marketing team with M.Gemi and working on everything from acquisition to social strategy.

Did you expect your blog, ExtraPetite, to become as big as it is now?

When I started, I just thought it was something I was really passionate about and wanted an outlet to share it. It took off, and there were a lot of people that could relate. Once it started becoming popular, I decided to invest more time in it and make my content as high quality as possible.

How has your blog’s approach to style evolved?

It was always a reflection of my own personal needs. When I started, it was more focused on readers who were starting out at work or just out of school. My content was focused on building a mature wardrobe that didn’t look like you were in college, but could still convert to weekends. After a few years, it was more about what investment pieces do you want to buy and how to edit your closet. Right now, [it] is focused on being versatile and mixing high and low, vintage and retail. My closet is at a mature stage, but I like to add a few great pieces every season.

—Rachel Raczka

Sam Vanderhoop Lee and Alex Caplow

  • Age
    24 and 25
  • Occupation
    Guitar and keyboard player; lead singer, Magic Man
  • Residence
How do you pack for the road?

Sam: I’m all about rolling things and putting them into little packing organizers. It keeps me sane, but Alex has a different system.
Alex: I’m more of a “shove everything into a small bag.”

Do you share your wardrobe?

Sam: We’ve definitely traded clothes in the past. Alex and I grew up wearing similar sizes, and we’ll always find that something the other one owns will fit me perfectly or better, or vice versa.
Alex: We’re pretty much always wearing the same black Levi’s skinny jeans.

Do you have a band aesthetic?

Sam: We’re not the kind of band that has costumes or would do a costume change in the middle of a set. But luckily everyone’s got a similar classic Americana style that we try to stick with onstage. Nothing too flashy or extravagant.
Alex: We pretty much wear onstage what we’d wear in real life, but we really do like fashion and looking clean-cut and put together.

Do you ever shop while you’re on the road?

Sam: We all love checking out thrift stores and vintage shops. Thrifting is all about not getting sucked into buying something you’ll never actually wear. That’s one good thing about being on the road — you’re not limited to always going to the same Savers every week. Being able to go to thrift stores all over really maximizes your chances of finding that one really awesome thing.
Alex: Some are awful and some are gold mines.

—Rachel Raczka

Jordan Piantedosi

  • Age
  • Occupation
    Artist and MassArt student
  • Residence
Who was your earliest style icon?

[Anime TV character] Revolutionary Girl Utena. She’s a knight and has a transformation sequence where her hair goes from short to long. She had a bunch of boyfriends, but also a girlfriend. She was a big influence on me in junior high because here was a female superhero who was also polyamorous.

How does one’s style communicate to others?

There are a lot of social cues that come with people’s appearances. I had really puffed-out hair for the past six months, but before that, my hair got long and blond, and guys would not leave me alone. When I cut and dyed it, everyone left me alone. Before that, I had this power mullet, and I thought it was this real '80s-hero haircut, but I ended up getting numbers from girls instead.

What does “dress to impress” mean for you?

When I go to MassArt, people are accepting. But in Boston, people tend to stare. I don’t necessarily like the attention, but I feel strongly about dressing in a way that I like, because when you do something crazy, it gives someone else who is scared permission to do the same.

—Perry Eaton Hair and makeup by Michaela Bosch

Khiara M. Bridges

  • Age
  • Occupation
    Ballerina, associate professor of law and anthropology at Boston University
  • Residence
    South End
How do you manage being both a legal scholar and professional ballet dancer?

It’s all about time management, discipline, and less sleep. I’m at Boston Ballet every morning at 10 a.m. taking ballet class and then, because I am an older dancer, I have to make sure my body stays healthy. So I take yoga as well. I work out three hours every day.

And where does fashion fit in the mix?

My being a dancer totally influenced the dresser I am. They’re known for using their bodies for art but tend to also express themselves through their individualistic dress. That fearless personality-driven style inspires me. I don’t think that will ever go away.

Tell me about your amazing tattoos.

I have peacock feathers on my back because I’ve always been described as ostentatious, and the peacock is the showiest bird [laughs]. On my ankles and calves are hibiscus. There was a hibiscus bush outside my parents’ bedroom in my childhood home, and it’s a tribute to them. I have law casebooks on my arms, and my favorite is when my book “Reproducing Race” came out in 2011. I got the last line tattooed on my shoulder blade.

—Tina Sutton Hair and makeup by Michaela Bosch

Anthony W. Richards II

  • Age
  • Occupation
    Executive director, Youth Design
  • Residence
How does creativity work into your day job?

I can’t draw at all, but I art-direct a ton of different projects. I give all the credit to the designers, but it’s about having that vision, and they have the skill set. It’s a perfect match.

Since you work with a younger set, how do you dress in a way that’s inspirational but not too stuffy?

Ninety percent of the time, I wear a crisp white shirt, and then usually a variation of a navy blue suit. It’s like the Obama look. Sometimes I’ll add a pocket square to dress things up a bit. Then I always wear a tie bar, and if I forget it at home, it’s like the whole day is ruined.

What got you into tie bars?

My dad and uncles wore suits every day in the '70s. It was fashionable, even if you were just hanging out with friends. When [my uncle] passed away, he left me his tie bar. I thought I can’t wear this, it’s too retro, but when I started wearing skinny ties, my fiance bought me a thinner tie bar from Jack Spade. It’s an easy way to add a little fashion into anything I’m wearing.

—Rachel Raczka Hair and makeup by Michaela Bosch

Lauren Wells

Did you change the way you dressed when you transitioned from advertising to owning your own business?

Not that much, though now rompers and shorts are acceptable for a workday, and that was definitely not true before.

You’re in a field known for creative expression. Still, are there rules?

If there are, I’m probably not following them. My personal rule is to always be original and true to myself. Comparison is the thief of joy.

Is there a common theme between your wardrobe and parties you plan?

Yes. If it isn’t meaningful or beautiful, scrap it.

What’s something we’ll never find you wearing?

High-heel wedge sneakers are a look I will never understand. Then again, I have been wearing denim overalls for years and I am sure people have similar thoughts about those.

What’s the last piece of clothing you purchased?

A mint green laser-cut dress from J.Crew.

If you could outfit guests for a party, what would the theme be?

A bohemian beach with lots of linen and whites, all soft and breezy. And flower crowns for all!

—Marni Elyse Katz

Graciela Rivas Leslin

  • Age
  • Occupation
    Designer and cofounder, Graciela Rivas
  • Residence
    North End
What’s your background with fashion? When did you decide to become a designer?

I always knew growing up that I wanted to be part of it somehow. I loved reading magazines and following designers’ collections. After I moved to Boston nine years ago to take business classes at Harvard Extension and decided to stay in this beautiful city, I started buying fabric and experimenting with my designs.

What was the first piece you made?

It was a one-sleeve cocktail dress in a brocade floral print. To this day it’s one of my favorites. It was a real party dress.

Who are the women you’re designing for?

Strong, independent women who live for fashion. Chic, elegant, and embracing their feminine side.

What designers and fashion houses do you admire?

Valentino, Marchesa, Carolina Herrera, Dior, Miu Miu, and Prada. And of course, Zac Posen.

How would you describe your personal style?

I am a very girly girl. I love dressing up and wearing high heels. Ruffles are my favorite.

—Rachel Raczka

Philip Saul

Is your men’s clothing store a larger version of your closet?

I wouldn’t buy anything for the store that I wouldn’t wear myself.

You were once Urban Outfitters’ district merchandising manager. How did that inform your style?

I learned a lot about thinking creatively, but rock ’n’ roll T’s were never me. I gravitated toward preppy vintage Lacoste polos.

You can’t live without...

A well-made oxford shirt. It can get you anywhere you need to go. Our private label oxford is my go-to. I have every color; blue is my favorite.

How do you make it your own?

By keeping it rumpled. I don’t want customers to think they have to iron their shirts. We are lived-in, casual, and comfortable.

What’s inspiring you right now?

The ‘70s beachside vibe from the original “Jaws” movie.

What’s hot for spring?

Joggers. The ones we’re carrying are khaki.

What’s your attitude on the Boston style scene?

It takes a little longer for trends to infiltrate, but that’s a good thing.

Long-term goals?

Ten Sault New England stores and a private-label line based on vintage finds. You’ve got to take risks, in fashion and in life.

—Marni Elyse Katz

Alina Roytberg and Lev Glazman

  • Age
    53 and 54
  • Occupation
    Cofounders, Fresh
  • Residence
How do you define your day-to-day style?

Lev: I love knits, T-shirts, great pair of jeans, great basics. For me, the definition of casual is comfortable. When you’re having a busy day, you don’t want to feel restricted. I need to feel like myself. I have a cashmere sweater by Italian designer Massimo Alba, a huge staple in my wardrobe. It’s the most beautiful shade of green, the most beautiful cashmere, and it makes every outfit. I have worn it for the past five years and it is still in perfect condition. It is my absolute favorite.
Alina: Casual doesn’t mean being sloppy. It means wearing something that’s still great fabrication. Getting dressed is like building a building. It’s all about your underpinnings and lingerie and your shoes, because that’s where it begins. You can never underestimate the importance of a good foundation to build upon. With shoes, it’s what puts an extra zap in your step.

—Rachel Raczka