Caroline Jackson on Little Women, the Small-Cup Bra Market, and Finding “Gorgeous Lingerie” in Every Size

For many years, women with smaller busts have likely wondered, at some point or another, why finding a good bra in their size can feel so needlessly complicated. Until fairly recently, being an A, AA, or AAA cup has meant hearing a frustrating set of assumptions: either that you don’t need bras at all, or that a bra made for a fuller bust can simply be sized down and expected to fit. The result, unsurprisingly, has left many women searching far longer than they should for well-fitting, beautiful lingerie that feels made with their bodies in mind.

One might assume a smaller cup bra would be less complicated to design, but Caroline Jackson would be quick to say otherwise. As the CEO of Little Women, a brand that has spent more than 35 years (yes, over three decades) making bras for smaller busts, she knows the work is in the smallest details, from flatter center panels and longer straps to shorter wires made specifically for smaller breast shapes. In other words, a good small-cup bra is not a scaled-down version of someone else’s.

“We are a small brand — albeit one of the only ones selling an AAA cup globally — and we are constantly trying to devise ways to reach customers who don’t know they can buy gorgeous lingerie and matching sets in their size in an affordable way,” she says.

We spoke with Caroline Jackson to talk about what people still misunderstand about smaller bust sizes, the Little Women bras customers swear by, and what the future of bra fitting might look like. Take a look below.

Little Women has been in business for over 35 years, and in that time, you all have helped so many women with A to AAA cups find bras that may have been difficult to come across elsewhere. What do you think people still misunderstand about smaller bust sizes and the women who shop for them?

People who aren’t small-busted often raise an eyebrow and ask why a smaller-busted person needs a bra. There are several answers to this, not least: Why wouldn’t a woman want to feel amazing in matching delicate underwear that makes her feel good? Why should size prevent that?

If there is any breast tissue at all present, it needs support – the Cooper’s ligaments that are at the back of the breast tissue can’t defy gravity. What about modesty? Why wouldn’t a woman want a smooth silhouette under a sheer top or T-shirt? Those are some of the reasons people who aren’t small-busted misunderstand the needs and wants of a smaller-busted customer.

While no bra is one-size-fits-all, there are definitely details that matter more for smaller busts, from shorter underwires to cups that are proportioned differently. From your perspective, what separates a good small-cup bra from one that just happens to come in a smaller size?

There’s a school of thought around what happens when lingerie companies just size up and size down from their standard “block.” This is actually really unhelpful and is a major factor for us in designing bras specifically for small breasts. This method doesn’t take any account of the bra wearer’s physiology or body shape, and why, for example, a small-busted woman needs a flatter center panel and longer straps. The wires are also needing a smaller spec because of the physiology (and fun fact, this makes sourcing very difficult.)

I’m really curious to know what the data says about women with smaller breasts, if there is any. Have you come across anything over the years that surprised you?

In all honesty, this is one of the biggest issues I have in running this company. Bra size isn’t a demographic in any measurable way, and this makes everything from deciding on styles through to marketing very difficult. Our loyal customers are great at giving us feedback, but anything more, say, intimate, is really difficult to ascertain, and a lot of our business decisions aren’t backed up with any specific measurable data, more based on “feelings.” We know the sizes that sell the best – way and beyond any other sizes – and these in and of themselves tell me that there is a market for small cup size bras, right down to specific band and cup.

The Perfectly You Bra has been a customer favorite for such a long time. What do you think has made it resonate with so many women?

I actually don’t know. It and its “sister,” the Very You, sell all day, every day. We’ve modeled many other bras on this pretty classic shape, but there’s something in the names that seems to make them a favorite. We’ve got two new continuity colors coming in shortly, and we’re really hopeful that they will join the best seller list.

I also want to chat about the Amour Ultra Padded Bra. What should women with smaller busts keep in mind when deciding whether a padded bra is right for them?

I think that women who want a very padded bra need to keep in mind whether they want this just for certain clothes or for all day, every day, and the whole mindset that exists around body image. By that I mean people shouldn’t be worried about a degree of “fakeness” in appearance – many of us dye our hair and have fillers and Botox done and wouldn’t expect that to be commented upon. However, putting a very padded bra on when you are normally flat-chested can affect you in different ways.

The lingerie industry has obviously changed quite a lot since Little Women was first founded. For one, women are shopping for bras online more often and getting fitted in person a little less often, especially with the rise of AI and virtual fittings. Where do you see the industry going next?

I think that the industry will get to the point where a woman can upload an image of her body to an app, and the app will do the sizing and recommend a bra for her breast shape. It seems the logical corollary to where we are at currently. We do virtual fittings online, and we use a sidebar quiz designed by lingerie specialists to help women find the right-sized bra already – it’s surely just a matter of time before it all gets done “real time” with no human lingerie expertise involvement.

With that being said, where do you see Little Women heading from here?

Oh, that’s the 64 million dollar question! We are a small brand – albeit one of the only ones selling an AAA cup globally – and we are constantly trying to devise ways to reach customers who don’t know they can buy gorgeous lingerie and matching sets in their size in an affordable way. My plans include developing our dedicated US site to reach the audience there and to keep spreading the word about our gorgeous, small cup lingerie.