Besties in Business

They say if you want to ruin a friendship, go into business together. But they haven’t met the owners of Forty Winks, Dress Boston, and Crush Boutique, three of Beacon Hill’s most elegant boutiques. Remarkably, all these stores were founded and are still owned by women who bonded early in life.

FORTY WINKS

53 Charles St.

Beacon Hill’s only lingerie store celebrates its first anniversary next month, but its owners, Meredith Amenkhienan and Rachel Wentworth, have long aspired to bring their brand to Boston’s toniest neighborhood. 

Amenkhienan and Wentworth met in 2007 when they worked behind the counter at Harvard Square’s Mint Julep, where they noted an interesting pattern. Customers were always asking where they could buy strapless bras to go under the glam party frocks. Intrigued, the two friends explored Boston’s retail market for undergarments. Victoria’s Secret sold sex appeal over comfort in the form of stiff push-up bras with mountains of padding. Department store lingerie sections had small, depressing selections, with no one to assist. “Women hate bra shopping! We started thinking, ‘wow, we could do this better—a lot better!’” says Wentworth.

Still in their 20s, the women wrote an extensive business plan for a lingerie store and looked for retail space in Harvard Square. At first, no one took them seriously. But with help from family and some unselfish mentoring from Mint Julep’s two female founders, Forty Winks launched in 2010. Bras are their number one seller, though Forty Winks has a variety of lingerie. They carry 90 bra sizes, which is more than most women know exist, with cup sizes from A to L and bands from 30 to 44. They have over 50 brands from all over the world and a generous range of styles.

Selling intimates is a delicate business, they explain, and a bespoke touch is the only way to do it right. “You can’t just stick customers in a dressing room with a bunch of bras and say, ‘Let me know how it works out.’ You have to get different sizes, help them adjust bands, evaluate the fit, gauge their reaction to the bra,” says Amenkhienan.

Wentworth adds, “You also have to give honest feedback that is gentle and takes into consideration people’s comfort levels around being half-naked in a fitting room with a stranger.”

This personal approach has attracted many loyal customers who want bras that match their specific lifestyle, career, or aesthetic preference. Some hate lace, while others have an aversion to underwire. Amenkhienan describes fitting an opera singer who couldn’t tolerate a band that restricted her ability to expand her rib cage. Even after almost 20 years in business together, the partners say disagreements are rare. “We communicate really well,” says Wentworth. “We always check in with one another. It’s so good to have a sounding board.”

The two are delighted to be celebrating their first-year anniversary in a neighborhood they love. “Beacon Hill is a great fit for us,” says Wentworth. “We have lots of friends here, and we are so happy to be part of the community.”

DRESS BOSTON

62 Charles St.

Martha Hilfinger Pickett and Jane Schlueter, the owners and founders of Dress Boston, Charles Street’s go-to boutique for luxury clothing and accessories, first locked eyes on the playground in fourth grade in Manchester, New Hampshire.

“Martha was new and a little shy. I just walked up to her and started talking to her,” said Schlueter.

The two became fast friends, poring over fashion magazines and playing sports on the same teams through elementary and high school. After college, they backpacked through Europe together. On the trip, they began to dream out loud about the idea of running their own clothing boutique.

Six years later, after a few jobs and a stint in Chicago, in 2005 they opened Dress Boston on Newbury Street, where they earned a reputation as sellers of elegant, timeless brands. In 2013, they moved to a space inside the Meeting House on Charles Street, and in late 2025, they doubled in size when they moved to their current location at 62 Charles.

Schlueter says, “Our goal was to offer exquisite clothing lines that you couldn’t find here, like Vanessa Bruno and Nili Lotan. We introduced those lines to Boston. Today they’re big names, but we’ve had those brands for twenty years.”

Like Beacon Hill, Dress Boston exudes quiet luxury. Pickett and Schlueter curate wardrobe staples—well-made clothing and accessories that promise to remain fashionable for years. The store’s racks feature luxe knits, refined outerwear, and glamorous but understated occasion dresses. Also on display are enviable handbags, shoes, and an array of fine jewelry.

The two women credit each other, along with a natural division of work, for keeping the business running smoothly. “Jane is smart, hardworking, dedicated, and has lots of big ideas. And she’s very fashionable, as you can see,” says Pickett, laughing and gesturing to her partner’s tailored denim dress.

Schlueter nods. “Martha is an innovative and genuinely caring person. We collaborate on everything.”

Their expanded space will allow them to double the amount of merchandise they can offer shoppers, which brings them joy.

“You have to constantly evolve to survive in this business. We have been around for 20 years, but we don’t have stagnant ways of thinking. We are always excited about bringing something new to our Boston customers,” explains Schlueter. “And we are very grateful to the Beacon Hill community for their support.”

CRUSH BOUTIQUE

138 Charles St.

WHITNEY + WINSTON

113 Charles St.

Crush Boutique owners Rebecca Hall and Laura Ayers vividly recall the day they met in September 1995.

“We were in eighth grade, in Mr. Lang’s homeroom class. Laura looked so stylish in her J. Crew outfit and her Rachel haircut,” says Hall. “I knew I was going to be friends with this girl.”

The two stayed in close contact through college and fantasized about opening their own store while on shopping excursions. The dream became a reality in 2007 when they opened Crush Boutique, a stylish shop in a garden-level space at 131 Charles St. that became the go-to dress and accessory shop for scores of local fashionistas.

In 2012, they opened a second location on Newbury Street. Three years later, the duo opened a new store on Charles Street called Whitney + Winston, a boutique that sells children’s clothing and gifts, named for Ayers’s corgi and Hall’s oldest daughter.

Both describe Crush Boutique’s aesthetic as sophisticated with a hint of whimsy. The clothes cater to a variety of situations and styles, from sedate to super glam. There are structured jeans, thick angora sweaters in baby blue and lavender, sleek silk bias-cut gowns, and look-at-me cocktail party dresses.

“We carry brands that are flirty, but there’s plenty of timeless stuff in the mix,” says Hall. “And a range of price points. We want boutique shopping to be as affordable as we can make it.”

When the pandemic hit retail businesses hard, the duo pivoted to selling pajamas and upscale leisure clothing online. Around that time, they closed their Newbury Street location to focus on reopening the Beacon Hill store in a much larger street-level space at 138 Charles.

“The biggest lesson we’ve learned is that you need to be malleable. If you can’t change, you won’t survive in this business,” says Ayers.

The two say they never had a conversation about who would do what. It just fell into place naturally.

“Good business partners need to know how the other person really works on all levels,” says Ayers. “I feel like we can read each other. Rebecca is very organized and has a great eye. She has a lot of energy.”

As for Hall’s perspective, she says of Ayers, “Laura executes the tasks that require deep focus. She’s calm, collected, and easy to be around. She’s the calm, and I’m the storm.”

The two support each other and their fellow Beacon Hill business owners in demonstrable ways. When Dress Boston opened its new space in 2025, Hall and Ayers sent them a bouquet of dahlias to celebrate.

Hall and Ayers are delighted that so many of their customers have become friends, who routinely consult the women on outfits for a succession of major life milestones.

“We have had the privilege of dressing some clients for their prom, then their first date, then their rehearsal dinner, and now are dressing their babies!”

Photograph by Claire Vail