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Cheryl Hudson-Jackson, Shir-lynn Brown, and Sherita Caesar have been friends for years. Hudson-Jackson and Caesar attended IIT together in the early 80s and met Brown later when she worked with Caesar at Motorola. About three years ago, Caesar, who was working in Atlanta at the time, was to receive a Woman of the Year award from the Technology Association of Georgia. Hudson-Jackson and Brown flew in for the ceremony.

Caesar had recently lost 25 pounds, and she’d bought a new dress for the occasion. But when she tried it on the day before, she found it didn’t fit as it had in the store. She cried a bit, then settled on another dress to wear.

When Hudson-Jackson and Brown saw her in it, they were speechless. “Sherita was swimming in that old dress, plus I had planned on wearing the same thing, so we had to find her something different,” Brown recalls. They had her try on the new dress again, but it was doing some serious sagging in the chest. Brown’s eyes met Hudson-Jackson’s. They walked over to their friend, stood on either side of her, reached under her dress, and hoisted up her bra straps. Instantly the dress fit fine.

Caesar, it turns out, was a fashion statistic. According to manufacturers, more than 70 percent of women in the U.S. are wearing bras that don’t fit. As they talked about the incident later, the three women agreed that someone needed to bring back the old art of bra fitting. Not a la Victoria’s Secret, “where the girls are walking around with a tape measure around their necks and measuring people over their outerwear,” Hudson-Jackson says. “You won’t get an accurate measurement like that. I mean someone who can look at you and tell you what size bra you need and in what brand, because each brand differs. Someone who can tell you where the support in the bra is, and someone who can help you get your breasts to sit just where you want them to.” As larger women, they’d all experienced difficulty finding undergarments and evening wear. They wanted a lingerie boutique that catered to the hard-to-fit. So they consulted with a few of their friends and drew up a five-year plan to do it themselves, naming their company Rubynesque.

All three women had well-established technical careers. But in addition to working for companies like 3Com, Hudson-Jackson had moonlighted in the lingerie department of Saks Fifth Avenue, just for fun. She’d been interested in lingerie since she was the lone little girl in a family of boys. Her mother and aunts had a passion for fine undergarments, and for her sixth birthday she was initiated into the club with a lacy slip, fishnet stockings, and a girdle. “I remember when shopping on Halsted or at Evergreen Plaza, back in the day, was an experience,” Hudson-Jackson says. “There was a lot of personal attention and time spent with a customer. Everyone got dressed to go shopping, and there was just so much style.”

Just a few weeks after the women hatched their plan, 3Com announced it was moving its headquarters to California and offered Hudson-Jackson a choice: relocate or accept a severance package. She took the package and plunged into the bra business. By February 2002 she was working full-time as president and COO of Rubynesque, learning the ins and outs of business licenses and double backstitching. She attended apparel shows in New York and Las Vegas and researched manufacturers and brands. Meanwhile Caesar, still based in Atlanta, has been serving as CEO; Brown, who moved back to Chicago from Florida last fall, is executive vice president for business and marketing.

The group decided early on that they’d start with a Web business–research showed that larger women like to shop for lingerie online. By April 2003 they’d launched a full-service retail site, Rubynesque.com. But they’d hosted a series of trunk shows as well, and the experience persuaded them that their knowledge and flair for custom fittings could also help set them apart from the competition.

At one trunk show, at the Marriott on North Michigan, they’d gathered a group of about 50 friends, family members, and colleagues. At first the guests were hesitant, but when the Rubynesque ladies began talking about their own “intimate apparel issues” and the wine kicked in, the shirts came off. After that show it was clear to the entrepreneurs that “women of all sizes needed premier lingerie custom fittings,” Hudson-Jackson says. “What we see under clothes–it tells us that women just don’t know what to do. Women just have drawers and drawers of bras that don’t fit, and we end up wearing that one bra that looks good with everything, and we wear it out.”

Most women should have five to seven bras in their wardrobe, says Hudson-Jackson. Playtex and other bra brands that use memory yarn, which molds to the shape of the breast, shouldn’t be worn every day–the fabric needs time to return to its natural state. Moreover, bras are like gym shoes: they need to be regularly replaced. An average-size woman should keep a bra no longer than six months, Hudson-Jackson says, while larger women should replace theirs quarterly.

Fit, of course, is key. Hudson-Jackson recommends a simple test: If your breasts fit in the cup and the bra is comfortable when fastened at the middle hook, your bra fits. If you have to go to the last hook to make the fit comfortable, your bra is too big or its elasticity has worn out; go down one band size–from 36, say, to 34. If you’re using the first hook, go up a size.

Rubynesque is expanding, with a brick-and-mortar store scheduled to open in far-northwest-suburban Vernon Hills next month. For city girls, Hudson-Jackson advises, Nordstrom’s lingerie department is probably your best bet.

“There is an art to bra fitting,” Hudson-Jackson says. “You have to understand how to measure appropriately, understand the make and model of all bras, understand the way breasts grow and the anatomy of a woman. But more than the technical aspects, you have to understand the intimate part of intimate apparel.”

Art accompanying story in printed newspaper (not available in this archive): photo/Dorothy Perry.