Inside Boston’s oldest year-round costume shop, Dorothy’s Boutique

Dorothy's Boutique owner Jon Diamond poses in a mask for sale inside his shop on Mass. Ave. in Boston, Oct. 30, 2019. Photo by Simone Migliori/ BU News Service

By Simone Migliori
BU News Service

BOSTON — When Jon Diamond was seven years old, he and his brother clambered into the family garage to try on hats. Merchandise from vendors filled the space—dressy, bejeweled hats, stockings, gloves and pocketbooks. Diamond’s parents were milliners, and they owned a growing retail chain in the Boston area. The store, Dorothy’s Boutique, sold the fashionable odds and ends worn by the city’s churchgoing masses. 

Diamond and his brother giggled as they tried on a pillbox whimsy, a fashionable hat decorated with an embellished veil. “People actually wear these?” he remembers asking his parents in bewilderment, only to find out that it was one of their best sellers. 

The boys weren’t just in the garage that day to goof off with the goods. Diamond’s parents enlisted their help ticketing the various accessories sold in the store. Dorothy’s Boutique was his family’s whole life, and by extension, his.

Shop talk spilled over from business hours into dinnertime. Diamond said that when his parents came home at night, it was never a question of what to make for dinner, but rather which restaurant they’d be ordering food from. 

Dinnertime chatter covered every detail of the store, from inventory to sales to curious customer interactions. “It was like, can we talk about something else besides the store? I understand you had a big day, but, you know, this is dinnertime,” he remembers thinking. 

From a young age, Diamond vowed never to take over the store, having seen the way it took over his parents’ lives. Now in his 60s, he’s owned and managed Dorothy’s Boutique for over 30 years. When he took it over in the 1980s, Diamond transformed the store into the costume shop it is today, selling everything from glossy wigs to Chuckie masks sourced from online vendors and his own creative thrifting. 

Owner Jon Diamond helps a customer find a costume wig in his shop Dorothy’s Boutique on Mass. Ave. in Boston, Oct. 30, 2019. Photo by Simone Migliori/ BU News Service

Diamond works year round to keep the shelves packed with bright makeup and colored contact lenses, plastic-wrapped costumes and unique party decor. But October is Dorothy’s busiest time of the year, with shoppers from across Boston descending on the store for goodies.

In the week leading up to Halloween, the store spends most of the day at capacity. Shoppers line up down Massachusetts Avenue waiting to get in to browse, Diamond said. But Dorothy’s Boutique faces new challenges as rent prices increase and online retailers loom. Worst of all, the building housing the boutique is slated for demolishing in a year. As a result, Diamond said he believes his career is winding to a close. 

Though he said he never saw himself joining the retail industry, endless odd jobs in his 20s wore Diamond down. In the restaurant industry, he worked his way up from dishwasher to server to manager. He lugged meats in a factory, worked as a trainer and lecturer, and served briefly in the corporate world. He calls himself a jack of all trades, who knows “a little about a lot.” After 10 years of exhausting work after college, Diamond was more than ready to take over the family business and be his own boss. 

“I can make my own hours and create my own destiny,” he said. “And I thought, you know, it’s an opportunity to do something. To maybe grow something that has a little bit more of my personality.” 

Diamond said he’s passionate about vintage items—from outdated radios to collectible baseballs —and he has an eye for finding gems among mounds of secondhand refuse. His love for vintage goods is part of what drove him to choose a costume shop as his retail vocation, he said. 

“I tried to find a niche where I can meet people and sell things to people and try to make it happen,” he said. “Boston’s a pretty good sized city, but to only have one costume shop? Are we really that boring?” 


In the chill of a windy October weekday, Diamond stood on the street behind the store loading four crisp-looking white chairs into his son Jesse’s car. Jesse needed a new set of chairs to replace the mismatched assortment surrounding his dining room table in Malden, and Diamond found a seller with a gently used Wayfair set. In his free time, he scours online marketplaces and vintage stores looking for treasure that he can give a second life to. 

He bought the chairs, then tightened up the bolts and screws before coating them in fresh white paint. “They do scratch sort of easy,” he reminds Jesse as he hoists them into the trunk. “You just have to be gentle.” 

Some of the goods at Dorothy’s are items Diamond has picked up from thrift shops in the Greater Boston area—a retro lava lamp, a collection of old-school tin lunch boxes, a perfect copy of Harley Quinn’s jacket from the movie “Suicide Squad.” The hodgepodge compilation of items makes the store a haven for costume-seekers in search of unique finds. 

Costume’s accessories behind the register at Dorothy’s Boutique on 190, Mass. Ave. in Boston, Oct. 30, 2019. Photo by Simone Migliori/ BU News Service

Amanda Stevens, 57, has worked for Diamond for three years, but said she’s been coming to the shop as a costume fanatic since she was 17. The two make playful jabs back and forth so often that Stevens said customers sometimes assume she’s his wife or daughter. “He has a very weird sense of humor,” she said fondly. “He’s a character all in himself.” 

Diamond’s friendliness is essential for working with Dorothy’s diverse customer base, Stevens said. Burlesque dancers, anime cosplayers, drag queens and college students preparing for themed parties frequent the store for outfits, jewelry, costume makeup and other accessories.

But Diamond can strike up a conversation with any customer that swings by the store.

“I like talking to people about anything,” Diamond said. No matter the subject, he keeps an open mind, and has a “hunger” for conversation. “It kind of keeps my brain going, and my wit, and my passion just for life,” he said. 

For Diamond’s son, Jesse, growing up in the store meant access to any costume a kid could dream of—from a Teenage Mutant Ninja Turtle to a blue Power Ranger. As an undergraduate at Boston College, he wowed his fraternity brothers with an inflatable “Fat Bastard” costume from the Austin Powers movies. Jesse remembers his father going above and beyond for customers every Halloween, taking special care to order outfits and accessories for people who couldn’t find exactly what they wanted in the store. 

“He was definitely in his zone,” Jesse said of his father’s long hours in the shop. “[He] wants to just make everybody happy.”

That means no costume request is too outlandish at Dorothy’s. “I keep an open mind, and I have a lot of vendors. And if I don’t have it, then I can make it happen for you—I can totally find it,” Diamond said. 

An endless assortment of costumes at Dorothy’s on Mass. Ave, Boston, Oct. 30, 2019. Photo by Simone Migliori/ BU News Service

When Jesse was younger, he worked at a YMCA camp, where he and the other counselors put on a massive battle role play for the kids. They dressed everyone up as barbarians and robots to fight, using costume accessories donated by Diamond. 

“It was kind of fun being a kid, right, with all this stuff for Halloween?” Diamond asked Jesse. 

Jesse said it was, but that he saw the toll that the hard work and dedication took. “[He was] very busy and stressed,” Jesse remembers of his father while he was growing up. “When you own a small business in Boston, it’s tough. And you’ve got to do what you can to get people in the store.” 


Before the crazy Halloween rush each year, when shoppers line up 30-deep around the block to get inside, Diamond stocks up Dorothy’s with costumes and inventory from his storage unit behind the store. A nondescript, padlocked door leads into the low-ceilinged unit, where plastic-wrapped costumes hang from metal poles. Spooky Halloween decor fills every nook and cranny, tucked behind plastic boxes and other storage. 

Usually, the room is stuffed full with hundreds of trendy costumes, Diamond said. But not this year. With rising rent prices and online retailers stealing customers away, business at Dorothy’s has dropped 40 percent in the last ten years, he said. Buying more inventory than he can sell is too great a risk.  

Glossy wigs on sale at Dorothy’s wig counter in the shop on Mass. Ave in Boston, Oct. 30, 2019. Photo by Simone Migliori/BU News Service

On the Monday before Halloween this year, Diamond sat at his compact desk, tucked across from the register. Shoppers pushed through the maze-like space of the store, clutching masks to their chests and ogling at brightly colored wigs in tiered shelves on the walls. Business isn’t bad this week, he reported with a broad smile.

He was exhausted after working in the store all weekend, but with his bright smile and boundless energy, it was impossible to tell. 

Leave a Comment

This site uses Akismet to reduce spam. Learn how your comment data is processed.