Little Women Is Launching World’s First AI Bra Fitting For Small Busts

Finding the perfect bra has never been easy for small-busted women – and with many high street retailers phasing out AA and AAA cup sizes, it’s getting harder. Caroline Jackson, founder of LittleWomen, has made it her mission to change that.

Now, she’s taken it a step further: partnering with AI fit-tech company Brarista to launch the world’s first AI bra fitting service for small busts. The new service uses Brarista’s AI Fit Chatbot to deliver expert bra fittings, style advice, and care tips for A, AA, and AAA cup customers – all from the comfort of home.

A soft red lace bralette paired with matching briefs styled under an oversized striped shirt — the perfect blend of effortless comfort and sensual minimalism. Ideal for elevating everyday lingerie drawers with a pop of bold colour. Credit: Little Women

Caroline shares how she revitalised an overlooked lingerie brand and why purpose-led innovation is key to making women feel seen (and properly fitted)…

The Founder Journey with Caroline Jackson:

What inspired you to start your business?

I purchased an existing brand, but my interest and passion was my background in retail buying – and my entrepreneurial brain loved the opportunity I could see in an underfunded and under-potentialised brand.

The initial steps to bring everything to life…

The business was already established but we implemented changes to the website to bring it into the 21st century. This involved a lot of research into the best platform for our business and obviously a careful implementation to ensure business continuity whilst we moved the existing – underwhelming – website to a new platform.

Some of the biggest challenges were…

This was in the relatively early days of e-commerce and my business partner and I had little to no knowledge or understanding of how e-commerce ‘worked’. We were pretty naïve about things like SEO and online advertising, plus there was not so much ready information around about e-commerce best practise so we were fumbling in the dark a little.

Social media was nowhere near as pervasive as it is now and we had to adapt to ‘survive’ in an e-commerce only niche. We also had never run a fulfilment based business either so it was literally learning everything from the ground up.

When it came to funding…

We were and are self funded.

A pivotal moment…

The implementation of the Brarista AI chat bot, plus the addition of our online fitting service (we believe we are the first to offer this service globally) have literally ignited our business.

We approach building a team by…

We are a very small team who have been part of the business for years. If we were in the position to increase our team one of the most important things I look for is how well they can get on with the existing team. I am a big believer in instinct and I usually have a good handle on whether someone is going to fit. In terms of leadership I aim to give everyone varied and interesting work to utilise their abilities and strengths whilst developing areas that they need more experience of or exposure to.

With a SME it’s not always practical or affordable to send people on lots of training courses and of course, not always relevant. However the team are encouraged to attend webinars and other information/training during their working hours so they can continually learn and develop their skills. I hate a silo mentality that says your job title is X so that’s the only set of tasks you should do. People have hidden talents and interests that I positively encourage them to explore – it makes for a job that they grow with for them and makes sound business sense for me with new ideas and directional suggestions that we can utilise.

Some strategies which have brought scale to the business…

It’s a continually iterating theme and one which we’ve literally this month decided to push harder to do more – and by that I mean putting some serious money into this. Having a PR service where the owner knows the lingerie business is hugely beneficial; our social media marketing has come on leaps and bounds since we employed a dedicated, in house content creator and we do everything we can to maximise the value that our new or existing customers feel at every touchpoint. Because we’re in a niche it’s always been challenging but we have made significant headway over the last few years.

A failure we made…

There have been loads – it’s the nature of the beast in a rapidly evolving market landscape. One of my most loathed mistakes was the purchasing of a massive spread of bralettes and matching briefs from the other side of the world and foolishly taking the suppliers word for it that it was a best seller in Asia and it would work really well for us. I naively placed the order without seeing a fit sample. The first time I saw it ‘on’ a person was at an e-commerce photo shoot and my heart sank. On a perfect sized model it looked absolutely terrible, just all wrong and we never launched it. Sadly there was no redress with the supplier and it was a lot of money wasted. Never again. But this is how we learn, not only through our wins but through our challenges and what doesn’t kill you often makes you stronger.

Credit: Little Women

We stay motivated by…

That’s a $64 million dollar question! I have moments when I think ‘why on earth am I doing this’ but interestingly just as my motivation might be flagging something good happens – big or small – that perspectivists the slump. I’m not a health and fitness kind of woman (I wish!) but I find dog walking makes for good headspace, or a salon treatment when I can block an hour or so out to have some time not working and when I’m blissed out having a facial or whatever is when my BIG ideas come. I’m a big believer in breathwork and wish everyone did it for their mental health!

Some advice to aspiring entrepreneurs…

This may sound strange but start off knowing what your exit strategy is. And by that I mean have your ideal roadmap ready that gives you the perceived stages that you imagine you want your business to go through, right to the point of selling / retiring. Not every business start up succeeds – we all know those stats – and not every start up is going to be the next Meta or whatever, but there is always space for businesses that solve problems or offer a service that provides value to the customer and which observe the best customer service model they possibly can. This is where the magic lies.

The Modems’ Byte-Sized Questions: