As a woman, I understand your struggle! But as a historian, I can answer with respect to British women from c.1400 to the invention of the bra at the turn of the 20th century!

The unfortunate thing with this debate is that there are not a lot of records from women discussing their personal struggles. Many would not have been literate, because neither were many men until the first drives for universal literacy in the 19th century. It is very true that some women were literate, and educated, but if any European aristocratic women kept a diary where they talked about these struggles of bustiness or even wrote home to their mothers about it, these records have been lost to time. Interestingly it is known that Mary Queen of Scots chose not to wear stays, so we can conclude that not all women did, but it is very hard to extrapolate that to the proportion of society that did. It is a sad but true fact that personal accounts of the lives of the illiterate, which were often women, poor, or otherwise at a societal disadvantage, are very rare indeed.

However, the sources that are available to us are artistic depictions of male and female dress; some surviving garments, especially from the Tudor period onwards; portraits of aristocratic women; records and inventories kept in these women’s households of clothes they bought or donated to charity; sewing instructions and patterns from the late 18th century onwards; and from the 19th century onwards, magazines and publications aimed at young women. It is difficult to know exactly how women felt about the garments available to them without resorting to speculation, but it’s definitely possible to know what at least the majority of women wore.

A woman’s shift was her primary undergarment, the one worn against skin, from the Medieval period, and did not start to change until the 19th century. It was a tunic assembled from simple squares and rectangles which women made at home in their houses, often from linen of varying quality depending on wealth. It was worn under the outer tunic, and later under stays and corsets, to keep the other garments clean. Linen could easily be boiled to wash, but stays, corsets, gowns and petticoats were much harder to launder, so the shift absorbed the body oils and sweat. Laundry was an expensive and laborious process so minimising it was important. There is no evidence that any supporting undergarment like a corset or bra was worn at all until the 1500s when Catherine di Medici helped popularise them. We can see in the illumination Dionysus I humiliates the women of Locri that shifts served the purpose of primary undergarment, regardless of how large-breasted the woman might be. Whether she suffered for this is impossible to determine, but other options were almost certainly not available in Europe until the 16th century. Such shifts would have at least stopped nipples showing through tunics and thus provided some modesty, if not support.

It is generally accepted that Catherine de Medici popularised corsets in the French court in the 1500s, but there are varying schools of thought as to how severe these were. There is a pervasive myth that she introduced iron corsets having banned waists bigger than 13” in her court, but this has been dismissed as impossible and apocryphal. The modern consensus, as put forward by authorities such as Valerie Steele, is that she brought a simple laced bodice, split into two parts and made of stiffened fabric, which shaped the body but not tightly. According to Keith Eubank, the surviving iron corsets were likely either novelty items or orthopaedic devices, not widespread undergarments as initially thought.

The fashionable 16th century silhouette was two cones, a conical skirt stiffened by a farthingale and and an inverted conical torso gently shaped by a split bodice, laced front and back and stiffened with starch and reeds. Such bodices, called a “pair of bodies”, with a decorative stomacher pinned over the laces, a triangular piece of stiffened fabric to fill the gap. Imagine the triangle with laces across down the front of a stereotypical “princess” dress and that’s what a pair of bodies and a stomacher would have looked like. Furthermore, the fashionable silhouette was actually based on the contrast between a narrow waist and large skirts, so stays actually served to flatten a larger bust rather than enhance it as with a modern bra.

“Bodies”, later called stays, evolved from outerwear in the 16th and 17th centuries to underwear by the 18th century. They because shorter with the empire-waist fashions in the regency period, and “short stays” were rather comparable to a longline bra. But no matter the style of the lacing, they were stiffened by reeds or whalebone, neither of which were very stiff. They would have certainly had a sculpting affect but women did not tightlace until the 19th century. When stays are worn loosely, like they were until the 19th century, there is a lot more room to adjust them with the laces by having the lacing closer together at the waist than the bust. Although they were almost always made at home or made to measure, there would have been a level of adjustability for, say, a busty peasant who was gifted old stays as an act of charity; donating clothes to the poor was a frequent act for wealthy women. Whilst there are no specific examples of large-breasted peasants and their corset-dealings due to a general lack of personal accounts of illiterate people, there are many examples of women donating clothes including stays to the general poor, as well as their own servants, so we know that women wore cast-off stays made to measure for someone else. Furthermore, existing specimens show how highly adjustable they were.

Steel busks and steel springs were a Victorian invention, as opposed to the wooden busks and reed stiffening of earlier. At this time, tightlacing began, but this was not a practice of working women. The women who could afford to limit their movements by tightlacing were the same women who could afford to have corsets made to measure, so they could be shaped to fit the fashionable silhouette even if they had a larger bust. Working women did wear corsets but because they didn’t lace them as tightly, they were significantly more adjustable in the fit.

Throughout the 18th and 19th centuries, “jumps”, unboned, short stays of quilted linen, were worn in informal situations for breast support and posture, whilst stays and later steel-busked corsets were worn more formally. By 1800, the primary purpose of corsets had become to support the breasts rather than flatten the torso, as waistlines rose. In many ways a corset was comparable to a modern bra in that it gave support without undue discomfort, unlike the extremes of aristocratic tightlacing in the Victorian era.

Bras as we know them today were born from the Victorian Dress Reform Movement, which eschewed stays in favour of “health” and loose clothing. It is disputed who truly invented the bra, but Olivia Flynt was granted a patent for the “Flynt-Waist” in 1876. She claimed her corsets were “healthy” and marketed them towards large-breasted women. Her adverts in magazines required the purchaser to answer nine questions on the reverse of the card before the initial corset could be fitted. This is an important example of how large-breasted women who couldn’t afford to commission a corset-maker might have procured a garment that fitted during the latter half of the 19th century.

The bra began as a divided corset, with separate sections for waist and breasts. The situation was not much different for large-breasted women in the early 1900s than it had been throughout the Victorian period, but things changed in the 1920s. “Bandeaus” and slips became the underwear of choice, with the slip worn over the bandeau for the first time; previously, a shift of some kind had always been worn beneath support garments. A boyish figure with flat breasts and straight hips was very much in vogue, and the bandeau aimed to flatten the breasts rather than enhance them. The Symington Side Lacer was marketed towards large-breasted women as it laced at the sides to flatten the chest, but overall the 1920s were not accommodating towards large-breasted women.

“Bra” was the most commonly used term to refer to the undergarment amongst 1930s college women according to a contemporary survey, and cup sizes A to D were first used in 1932, although “small, medium and large” were still largely used until the 1950s. By the end of the Second World War, the “pointy bust” fashion had led to bras becoming almost ubiquitous, although large and “unusual” sizes were in short supply.

It could be argued that the eras of adjustable stays gave women the greatest flexibility, although sadly we may never know what most women thought of their stays before the 19th century so it is impossible to make a proper comparison. But options were definitely available for large breasted women in some capacity, once supportive garments had become widespread.

Edited slightly for clarity