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People, Feature, Style & Beauty,

The 19 Best Dressed People in Boston

By Abby Bielagus By Abby Bielagus | April 24, 2025 | People, Feature, Style & Beauty,

Whether they’re sitting front row or gracing our feeds, these style stars and their inspiring looks reign supreme.
AJ WILLIAMS PHOTO BY MELISSA OSTROW
AJ WILLIAMS

AJ WILLIAMS

WHO
With 25-plus years as a producer and event designer, the founder of AJ Events has been the creative vision behind Boston’s most coveted parties

BECAUSE
When the lights are finally on her, she shines in full glam

SEEN WEARING
Dolce & Gabbana, Chanel, Loewe, Max Mara, Victoria Beckham, Proenza Schouler, Prada, and McQueen

ALAN
AND BÊ
BILZERIAN PHOTO BY MICHAEL
BLANCHARDALAN AND BÊ BILZERIAN

ALAN AND BÊBILZERIAN

WHO
Husband and wife cofounders of the designer boutique Alan Bilzerian

BECAUSE
For over 50 years, they’ve been Boston’s fashion gurus with their commitment to clothing as the pages in everyone’s individual story

SEEN WEARING
Prada, Comme Des Garçons, Yohji Yamamoto, Issey Miyake, Carol Christian Poell, Undercover, Junya Watanabe

BRAN
RAFANELLI  PHOTO BY MATT TEUTEN
BRAN RAFANELLI

BRYAN RAFANELLI

WHO
The founder and chief creative officer of Rafanelli Events is known nationwide for his uniquely curated visions, most notably for his White House decor and famous weddings, including first daughter Chelsea Clinton

BECAUSE
His own personal style is almost as well-known as his events

SEEN WEARING
Gucci, Bode and Todd Snyder

ELISHADANIELS PHOTO BY JUAN CARLOS GONZALEZ
ELISHA DANIELS

ELISHA DANIELS

WHO
The designer, stylist and author runs an eponymous style studio and boutique at the Mandarin Oriental

BECAUSE
Her joyful, colorful ensembles are reminiscent of Mad Men, Iris Apfel and the Upper East Side, and on red carpets or everyday sidewalks, they are always memorable

SEEN WEARING
Wes Gordon for Carolina Herrera, Elyce Arons for Frances Valentine, Alan Anderson Jewels and Marquise Paris Bags by Elizabeth Busson

ERIC ROSEFF PHOTO BY FREDERICO DI LALLO
ERIC ROSEFF

ERIC ROSEFF

WHO
The fearless and bold founder of interior design firm Eric Roseff Designs

BECAUSE
His innovative and eclectic taste reinvents rooms within four walls and a wardrobe when he wears it

SEEN WEARING
Gucci, Tom Ford, Ralph Lauren, Rick Owens, Cos, Mr. P. and Paul Smith

ERIN GATES PHOTO BY JESSICA DELANEY
ERIN GATES

ERIN GATES

WHO
The founder and principal of Erin Gates Design is also a New York Times bestselling author and designer for her growing global lifestyle brand

BECAUSE
The woman behind the brand is her own best advertisement

SEEN WEARING
Veronica Beard, La Ligne and Cara Cara

HERV
JEANBAPTISTE PHOTO BY: AARON JAMES
HERV JEANBAPTISTE

WHO
The creative consultant and tastemaker is also the host of SILK, one of Boston’s hottest R&B parties

BECAUSE
His standout style competes for snaps with his drive to lift up emerging talent

SEEN WEARING
Brainchild, PHASE, and Jayemade

JACK YEATON PHOTO BY: MICHAEL BLANCHARD
JACK YEATON

JACK YEATON

WHO
The PR guru who once helmed his own firm is now bringing his talents to his role as the senior manager of creative and marketing at Jamestown

BECAUSE
His uncanny ability to mix the irreverent with the classic and his impeccable eye for jewelry and accessories make him a standout from the gala circuit to weeknight dinners

SEEN WEARING
Brunello Cuccinelli, God’s True Cashmere, Chrome Hearts eyewear from Riccardi, Back At The Ranch cowboy boots from Santa Fe, 1971 Rolex Paul Newman Daytona Ref. 6263 and Acqua Di Gio by Armani

LAURA
BALDINI PHOTO BY: MICHAEL BLANCHARD
LAURA BALDINI

LAURA BALDINI

WHO
The co-founder of Mother Juice also launched her own line of handbags called The Flie

BECAUSE
Her effortless, feminine style always feels fun and never forced

SEEN WEARING
Rick Owens, Alexander McQueen, La Ligne, Zimmerman and Ula Johnson

SINESIA KAROL PHOTO BY: DANI SILVA
SINESIA KAROL

SINESIA KAROL

WHO
The designer behind the beloved eponymous swimwear brand

BECAUSE
Her easy, breezy style brings summer vibes all year round

SEEN WEARING
Fendi, Valentino, Dior, and Hermes

LISA
PIERPONT PHOTO BY CHERYL RICHARDS
LISA PIERPONT

LISA PIERPONT

WHO
The producer, media wiz and former editor of Boston Common is an adjunct professor of broadcast journalism at Emerson College

BECAUSE
Her talent for showcasing the cool is clear from her urbane style with edge

SEEN WEARING
Prada, Dries Van Noten, TWP and Daniela Corte

LYNN
DALE PHOTO BY NICOLE BAAS
LYNN DALE

LYNN DALE

WHO
The maven behind Lynn Dale Events and all-around gal about town

BECAUSE
Celebration is in her DNA, and she looks flawless at everything from museum openings to black tie soirées

SEEN WEARING
Paule Ka, Delpozo, Benvenieste, Edeline Lee, Cucinelli, Louis Vuitton, Akris and Fendi

MAWUENA
DAVIES PHOTO BY: MAWUENA DAVIES
MAWUENA DAVIES

MAWUENA DAVIES

WHO
The jet-setting photographer and stylist who is often his best subject

BECAUSE
His eye for creating complete looks from unique, often vintage pieces is unmatched

SEEN WEARING
Indi & Ash, Black Sign, Sillage, Todd Snyder, William Frederick, Engineered Garments, wmenswear, Oni denim, Fried Rice, Pigeontree Crafting, Bleu de Chauffe, Alden, Viberg, and Thomas Farthing

MILLICENT CUTLER PHOTO BY: MADISON MEYER
MILLICENT CUTLER

MILLICENT CUTLER

WHO
The owner and creative mind behind lifestyle boutique Ouimillie

BECAUSE
She blends sass and class while always mixing it up in colors and prints

SEEN WEARING
enmoyal, Rachel Comey, Alysi, Isshi, Martinez and Hanna Norris x Ouimillie

PAMMY
WILLIS PHOTO BY: TOAN TRINH
PAMMY WILLIS

PAMMY WILLIS

WHO
With her chef husband, she owns the acclaimed Pammy’s restaurant

BECAUSE
Her megawatt smile and eyecatching gray curls are always the best accessories for her bold and joyful style

SEEN WEARING
Essential Antwerp, Phillip Lim, Stine Goya, Hermes, Sandro and Iceberg

PHILIP SAUL PHOTO BY: MARK DUNN
PHILIP SAUL

PHILIP SAUL

WHO
Founder, owner and creative director of SAULT New England boutique

BECAUSE
He makes preppy cool

SEEN WEARING
Forét, Sault New England

SEAN WILLIAM DONOVAN PHOTO BY MICHAEL BLANCHARD
SEAN WILLIAM DONOVAN

SEAN WILLIAM DONOVAN

WHO
The interiors and prop stylist makes every space look beautifully photo-ready

BECAUSE
He’s classic like JFK Jr., fancy like Gatsby and effortless like Redford

SEEN WEARING
Todd Snyder, Sault NE, Banana Republic, Alex Mill and Abercrombie jeans

WINSTON SIMONE PHOTO BY MICHAEL BLANCHARD
WINSTON SIMONE

SIMONE WINSTON

WHO
Philanthropist and founder of The Newbury Cup

BECAUSE
She can make even a T-shirt and jeans look regal

SEEN WEARING
Khaite, Cult Gaia and Caroline Herrera

JANET WU PHOTO BY MICHAEL BLANCHARD
JANET WU

JANET WU

WHO
The former 7News and Bloomberg anchor is a frequent moderator at panels and events around town

BECAUSE
Whether she’s on television, a guest at an event or the evening’s emcee, she knows exactly how to dress for her petite frame in time-honored styles

SEEN WEARING
Roland Mouret, The Row, Victoria Beckham and Andrew Gn



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Photography by: PHOTO BY MELISSA OSTROW, MICHAEL BLANCHARD, MATT TEUTEN, JUAN CARLOS GONZALEZ, FREDERICO DI LALLO, JESSICA DELANEY, AARON JAMES, DANI SILVA, CHERYL RICHARDS, NICOLE BAAS, MAWUENA DAVIES, MADISON MEYER, TOAN TRINH, MARK DUNN

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