Most Stylish Bostonians

You have several jobs. How do you maintain a wardrobe for all of them?

I wear four hats, but I basically wear black skinny jeans, little Gianvito Rossi boots, a T-shirt, and a The Row sweater so I can go from one job to the next. I have a massive pile of Calypso St. Barth linen and cotton shirts. I’m hoarding them [the brand folded in February]. And I think I have 20 Rick Owens jackets. I’m a one-trick pony. I wear a lot of black. Black, to me, means you can come and go as you please.

What about if you have an evening event?

I love the hardness of a leather jacket with a gown.

You also travel a lot. What’s always in your bag?

Daniela Corte’s waxed pants are in my bag — one of her little tops and definitely a big Rick Owens wrap or sweater. You can use it as a bathrobe or throw it over jeans.

Where do you shop?

Saks, with [personal shopper] Suhail Kwatra. Or at Alan Bilzerian. They usually have things other people don’t have. And by the looks of my American Express card, I shopped quite a bit with Daniela Corte last year.

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

Furry boots.

How has your style evolved?

Honoring my Caribbean and African roots has been the biggest influence. Specifically, the way I wear my hair. Five years ago, I stopped chemically altering my hair. To be able to fully embrace it, with all its kinks and curls, has been a major shift in my life. As my hair grew more wild, my spirit followed. I feel more self-confident. I think my clothing style evolved with my hair.

How do you dress for a typical workday?

I work with a housing advocacy agency — I believe housing is a human right — and need to dress for many situations in a given day. You can’t go wrong in a black turtleneck and wide-leg pants. They have become a crutch, but I won’t put them down. They’re stylish and functional.

And on weekends?

I’m obsessed with my denim jacket from the Gap. It has a hummingbird embellishment on the shoulder and a butterfly on the sleeve. I love dressing up. Knee-length skirts and blouses work with my hourglass figure.

Do you have any style resolutions for spring?

I am challenging myself to experiment with more color. Instead of reaching for the little black dress for the hundredth time, I’m going to grab the pink sundress from the back of my closet. I’m not afraid to rock a red lip. I have a heritage of happy color that I want to carry with me.

Would you say the glasses are your signature?

I’d have no identity outside my glasses! They’re Winston from Warby Parker. I have seven pairs because I’m afraid they’re going to discontinue them.

Is your decorating style similar to your fashion sense?

I dress like my home looks. I dress like people can give me a hug. I’m super casual, I don’t seem breakable. Comfort is my number one priority.

How casual is casual?

Jeans, a #BOSSLADIES sweat shirt, and Gucci shoes, either leopard mules or red velvet loafers. The statement shoes are like the bold jewel-tone sofas I use in my decorating projects.

That’s a far cry from your days as a prosecutor.

I still remember the jacket that would change my life. I bought a black jacket, pencil skirt, and white pussy-bow shirt with black polka dots at Benetton. It made me feel like a lawyer and gave me confidence to take the bar [exam]. My first step was always to dress the part. Clothing has the ability to transform you.

What other fashion personas have you adopted?

When I first became a stay-at-home mom, I adopted the “yummy mummy” uniform — tight skinny jeans and flowy, boho top. After my second son was born, I realized we were never going to move to the suburbs, that I hated jewelry, that the whole look wasn’t me. I cut my hair, bleached it, and started wearing the black glasses.

What will your next style iteration be?

I think my 40-year-old self is going to be sexier.

You’re pregnant with your third child. Congratulations! Any maternity style tips?

My winter uniform was a dress with black tights and boots. I’ve been trying to spice that up with pattern, especially for spring. Primark makes a good non-maternity tunic that works well, and ASOS.com has flattering, affordable, trendy maternity wear. A friend just turned me on to Le Tote, which is style by mail, and they have maternity. They send two boxes a month; you keep what you like. A Pea in the Pod is good for special occasions. Their nursing bras are worth every penny.

You mention trying to incorporate pattern. Have you been successful?

Lately I’ve been very attracted to Marimekko. I appreciate the stories and history behind the designs. I like the simplicity of the cuts and fabrics; of course, the patterns are anything but. I have two loose A-line dresses, one in a taupe poppy print, and the other with big black and white polka dots. I also have a pair of cropped work pants with a beautiful oyster-shell print.

What about color?

I’m co-chair of the BCA Ball for Boston Center for the Arts in June. I will dress colorfully. I’m thinking bright, colorful patterns. I was in Miami recently and felt really inspired by the murals in the Wynwood district. They make you want to take a lot of selfies. It’s like they’re saying, “Go bright and go big or go home!”

You attend a fair number of formal events. What designers do you love for evening?

I have been wearing Marchesa Notte a lot recently — to the Juliet’s Ball, the Storybook Ball, and the Green and White Ball. [Designer Georgina Chapman’s] dresses fit me really well; I feel good in them.

What’s your process for choosing evening looks?

I scroll through Moda Operandi, Net-a-Porter, and Farfetch, picking a few that are a bit unexpected, but still appropriate. I choose styles that reflect my personality. It’s important that the dress be physically comfortable.

Tell me about your e-boutique NEWMA.

I gravitate toward unfussy, stylish, comfortable pieces with a touch of coolness, from European and American brands that are not well known here. This spring we’re carrying a new Spanish shoe line, About Arianne, as well as WHIT, a new [women’s wear] brand out of Brooklyn.

Which did you buy for yourself for spring?

I got the WHIT Day Dress with big, muted, rainbow stripes and simple tie waist. Our About Arianne Tina shoes in both sunset and lime go perfectly with it.

Dresses or shorts for summer?

Definitely dresses. It’s so easy to throw on one piece and look pulled together.

Are you a jumpsuit and romper person, too?

No. Alexa Chung wears them adorably, but I think I’m past that age.

How would you describe your style?

I’m really inspired by travel. It’s a blend between French, Japanese, and street flair. I like geometric shapes of clothing and graphic prints. I went to Japan last year and adjusted my personal style. I don’t think you need to wear form-fitting clothing. I like pieces that have good shape.

Where do you find most of your pieces?

I like to go thrifting when I travel, and I’ve been lucky to have really creative friends who are designers or textile artists. [Leathersmith] Gina DeWolfe made my go-to bag, and Jordan Piantedosi has made some really great textiles for me. I like wearing the work of emerging designers. It’s like wearing art.

What’s been your best thrifting find?

I found this red corduroy jumpsuit from the ’40s or ’50s in San Francisco. I’ll wear it with just sneakers, or I’ve put on red lipstick and some heels and worn it to black-tie events.

Do you have a go-to vintage shop?

I love Boomerangs because they support the AIDS Action Committee. You’re shopping with intention and going to a purpose-driven store that’s also lowering the footprint of waste from fast fashion. That’s important to me.

Is there any artist whose personal style you admire?

Frida Kahlo — she was always layering textures and patterns and color. And beyond what she’s wearing, it’s her confidence.

Do you think your curator’s eye shows up in your personal style and vice versa?

You can see it in “Menagerie,” my current show [at Gallery Oh!]. It’s juicy, lively, eclectic work by a lot of international artists. It’s both graphic and refined. I would wear this art show.

Where do you shop?

My favorite place for fun things is Rainbow in Jackson Square. It has the weirdest things, fun accent pieces that cost like $7. I just got a pair of flowered high-heeled boots there. There’s this Bulgarian woman who makes almost industrial-style pieces on Etsy, Maria Queen Maria. [I like] Aritzia. If you’re petite, the pants fit great, and the clothes are really well made. They’re more expensive, but for basic items, it’s worth it.

How does your “civilian” wear differ from your performance outfits?

My clothes are a microcosm of the demands of a professional artist. Historically, artists transcended class. Artists were often poor or at best middle class, but they had the social skills and wherewithal to pass as a rich person, to not make their patrons uncomfortable. I like big and flashy and fun, but you will never, ever see me rocking a Burberry bag (fake or real) or any overt class stamp. That’s why if I have a really cool and pricey pair of shoes, I’m going to pair it with something from the thrift store or Rainbow. Plus, it makes my very small budget work!

If you’re traveling to a show, what’s in your suitcase?

A couple of suits, leather blazers, black pants, black lace shirts, a bunch of high heels, lots of jewelry, and a lot of eyelashes. I love fake eyelashes.

Who are your fashion icons?

David Byrne. Prince. Barbra Streisand. It doesn’t feel like they’re trying too hard. They’re taking risks, but it somehow becomes an identity.

Is there anything you wear every day?

A rope bracelet that I get redone every summer at Impressions in Northeast Harbor, Maine. It’s three strands wide and she literally ties it to my wrist so I can’t take it off.

How do you make sure your style stands out?

I like the balance between classic conservative and funny whimsical. My sister gave me an L.L.Bean button-down shirt and she had it embroidered with “BRO.” So now I get everything monogrammed with things like “HUH” or “SUP” or “LIT.” I even have one that just says “NO.” I usually wear that on Mondays.

Who is the Duende man? Who inspires your shoe designs?

I like creating things that appeal to someone who might normally say, “This isn’t my style.” I’ve been at trunk shows where a mom will see a classic shoe, but then the son will see my pair that say “FML” as a monogram and be like, “Oh my God, I have to have those!” I like riding that line — classic with a humorous twist.

Can you credit your style to any particular fashion icon or era?

One of my friends commented on my Instagram post, “You look like you’re dressed for a party in Star Wars,” and I was like, “Greatest compliment ever!” I always see movies where [the wardrobe makes me say]: “I’d kill to own that.” Like the suits that Mayor Larry Vaughn wears in “Jaws.” They’re pastel madras, and they’re ridiculous and amazing.

What’s your earliest style memory?

There was a sweater that was itchy with a bright, bold stripe and three trucks across it. I remember wearing that a lot. In middle school and high school, I tried to blend in more and wore plainer clothes. But now I’ve gone back to loving how my mom dressed me as a kid. I’m like, “Do they make that whale sweater in adult sizes? Because I’d wear that right now.”

How would you describe your style?

I don’t like to define myself because it’s different from day to day. Comfort plays a big role. I’m really active, and I like to be able to move freely.

What are defining pieces in your wardrobe?

A friend of mine from MassArt started Bandulu Street Couture. The clothes look like they have paint splatters all over them and you look like a dirty artist, but when you go up close, it’s actually beautiful, intricate hand embroidery. And Kristin Texeira, another visual artist from MassArt, creates one-off pieces that look like her paintings. I have a crewneck by her. I try to wear them around town and be their hype man.

Who would you call your style icons?

Mark Gonzales, a skateboarder and all-around artist. I’m really inspired by the way he dresses and just the way he is as a person; he’ll be in baggy crewnecks, whipping around the city on a bike with a cigar in his mouth. And [designer] Ouigi Theodore, who has such classic vintage workwear style. He just dresses so well. I’ve been drawn to really good old-man style, like a nice cardigan and some glasses.

Where do you like to shop? NEW

Orchard Skateshop and Bodega and Vivant Vintage. I like supporting local, and these people are my friends. It’s like how I support the people who create my favorite pieces. I like to support the stores that foster a creative community as well.

Do you think there’s any crossover in being a creative professional and dressing the part?

Self-expression and having your own voice plays such a big role — fashion is a big part of it, whether you’re aware of it or not. Getting dressed is just another form of expression. However far you want to take that is up to you.

How did you dress growing up in Flint, Michigan?

My family set the tone. My mother definitely had an eye for style. And one of my uncles would always travel with a hatbox and dress to the nines. In high school we had a uniform to wear, a light blue shirt and navy pants. I always had to have socks with something going on, like mismatched or with polka dots. I never thought in terms of outfits when I shopped. It was more about individual pieces.

When traveling to work with orchestras across the country, are you a good packer?

For the last several years, I’ve done work where I have to be gone for a week at a time. I started to make Excel spreadsheets that are color coded. Since I can’t do laundry the whole time, I have to plan what to wear each day.

What are your favorite local stores?

I’m an old-school prep at heart, so Brooks Brothers and Polo Ralph Lauren.

Do you wear bright colors mainly in the warmer months?

It’s all year round. I just like bright color and don’t feel like it’s a seasonal thing. I like colorful pants, and the pants will determine the rest of the outfit. One of my favorite pants in the winter are yellow corduroys that I got at an outlet for $6 because no one wanted that color. Just because it’s drab outside doesn’t mean you have to personify it.

How did the Paris Fashion Institute change your personal style?

I always had my own style, but going to Paris changed the way I look at fashion for myself. It gave me more confidence to go out there more, rather than playing it safe.

You are the ultimate mixer of old and new. How do you weed out your closet?

I don’t weed out my closet! I look at trends, but I never throw anything away. Some of my clothing I’ve had forever. I keep everything, absolutely everything. Early on, I worked for the Gap for 14 years, so I probably have every fit of denim and vintage piece from that time. I like to pull out those old classics and mix [them] with new things I buy or make. And I’m still using fabrics I’ve had for 10 or 15 years.

What current designers do you admire most?

The designers I really like — Balmain, Balenciaga, Rick Owens, Prada, Gucci — are not so much for menswear. I find women’s wear more fanciful and less utilitarian, so I look at the new collections and then interpret it in a look for me. I don’t really want to look like everybody else.

What’s your personal fashion goal?

Whenever I go to an event, I most probably am wearing something I’ve made, because my clothes speak for me. I’m kind of shy. I let what I look like be me.

Do you have vestiges of Southern style in your closets?

DP: I used to wear cowboy boots when I lived in the South. I’m from Memphis. I don’t wear them anymore, though a lot of guys on the team wear them. I probably dress more like a West Coast kid now.

CP: When I first got to Vanderbilt [University] — I’m from the Bay Area — I was surprised that traditional female tailgating attire was sundresses and cowboy boots. It was part of the culture and really fun. The closest thing I wear to cowboy boots now are my Chloe studded booties.

What are your favorite styles and brands these days?

DP: I like Paige denim, Vince, Theory, Rag & Bone, Cotton Citizen, Frank & Eileen, and Alo Yoga. For shoes it’s Nike, [Christian] Louboutin, and Tom Ford. You can go crazy with the Louboutin. I don’t wear the spiky ones, but some guys do. I also have a lot of Happy Socks. I wear them to match my outfits. I have four-leaf clovers, palm trees, different color stripes, every color of camo.

CP: My favorite designers are Rag & Bone, Alexander Wang, and Gucci, and I love Valentino. I alternate purses a lot. I like the Fendi bags with the artistic straps and the Valentino bags with spikes. I have the new Valentino Rockstud Spike bag in pink. I love pop art, especially Mel Bochner. That influences the designers I gravitate toward, like Missoni’s mix-and-match patterns in the zigzag and florals.I buy most of it online, at Revolve and Forward by Elyse Walker.

Any favorite Boston boutiques?

CP: I model clothes for Max & Riley; sometimes Drew takes the photos. I also work with Crush Boutique on behalf of the Christopher’s Haven organization that provides housing for families whose kids are getting cancer treatment. Each Red Sox wife walks with her child or a child from Christopher’s Haven in an annual fashion show. I spearheaded last year’s. Crush supplied the clothing.

What’s typical game-day attire?

DP: I have a black pair of Louboutin sneakers that I wore every day I pitched last year — before going out on the field, of course.

CP: In Boston I might wear black skinny jeans with a white stripe, heeled Valentino booties, an IRO leather jacket over a long-sleeved shirt, and a Celine Micro Luggage crossbody bag, because it doesn’t scratch easily. In summer, it’s a sundress with wedges and sunglasses.

Is there a look of Carolyn’s that you like or don’t like?

DP: I love when she wears tight dresses, because she went through a loose silk dress phase; I’m not a fan of those.

Does Carolyn do a lot of the shopping?

DP: She shops for me sometimes.

CP: He has a great sense of style. Baseball players are very fashionable; his team provides a lot of inspiration. I’m the final stage of approval.

You’re from Brazil, worked in Ukraine, and now co-manage a global company. Does dressing for success change from country to country?

Yes, absolutely. For example, I worked in Rio and Sao Paulo, where people are dressed for summer all year round. I was a little shocked [by] what people wear to the office, like super cropped tops and showing a lot of skin. It’s just like a resort-type atmosphere, and it’s fine and acceptable there.

In Ukraine, women try to be very sexy and feminine. It’s not perceived as being vulgar or in bad taste. They wear high heels to the zoo! Working there transformed the way I dressed. I became much more conscious of my feminine side.

Boston in particular is very conservative. At my first tech meeting I wore black tight leather pants, which are like jeans in Ukraine. People looked at me like, “How dare you?” So I had to find pieces that I like from the different cultures and find my own way to dress.

Does your efficiency in business translate to clothes shopping?

I do probably 90 percent of my shopping online, and my number one place is Farfetch. I try to get some business benefit out of the shopping experience, so I like to look at fashion startups to check new customer experiences, business models, et cetera.

Describe your style.

Feminine, edgy, casual. It’s full of contradictions, so I’m not too formal, too casual, or too anything.

As twins — especially twins who work together — how have you been able to define your individual styles?

AH: We haven’t. We’re those weird twin best friends who never felt the need to distinguish ourselves from each other.

KH: We’ve always had a similar taste in style. Growing up, we’d like the same pieces, and instead of buying two of the same item, we’d agree to share it.

What are your favorite “hype” brands?

AH: You can’t mention hype without mentioning Supreme. I know some people say it’s died, but I think it’s probably the most affordable hype brand even though it’s physically difficult to get. It’s a lot of refreshing your Web browser.

KH: Alyx, Heron Preston, Off-White, and Ambush.

AH: And MISBHV, because of the creative minds behind them and the young fan base they’ve garnered.

Is Boston ready for this level of fashion?

AH: It’s already here! You can find most of those brands between Riccardi and All Too Human, two of our favorite stores. Plus, SizeRun [Supply] in Brookline resells Supreme, and Concepts and Bodega come in clutch with sneakers. When you pay attention, you’ll notice there’s a huge hype community here. And everyone’s crazy supportive of one another.

For someone just discovering your Instagram account (@thehesstwins), it’s kind of impossible to tell who is who in the solo shots. Is this on purpose?

KH: It’s not not on purpose. We don’t strictly intend to obscure our individual identities . . . it’s always been more about the style than the person showcasing it.

Do you consider yourselves “sneaker heads”? What are your holy grails?

KH: The term makes us uncomfortable . . . the fact that it’s historically been gendered male due to sneakers’ association with sports and sports’ association with men.

AH: We were actually talking about this the other day, when I read a headline with the phrase “female sneaker head.” Reinforcing this idea is the fact that the majority of hype sneakers didn’t use to come in sizes small enough to fit women.

KH: But do I consider myself a fan of sneakers? Absolutely. My favorite pairs are my Chicago Jordan 1s and my Off-White Nike Prestos.

AH: Mine are the Aleali May Air Jordan 1s — they have a black corduroy upper with a silver satin toe.

How do you feel about the sustainability of fashion blogging? What’s the next step?

KH: It’s something from which we’re slowly backing away. Not to say we’re leaving it behind completely — it’s more that our time and effort will be channeled into a new venture that we’re really excited about. Without completely spoiling it, Ashley and I are working on developing an online service that will provide luxury streetwear and contemporary fashion rentals. We’re looking to launch within the next six to eight months.