There isn't a lot of originality in fashion - she's seen the roundabout of trends come and go, some good, others bad - namely tight ribbed "bubblegum jeans" which "thankfully" never made a comeback.
"I have got to the stage where everything is coming around for about the third time - it all goes through the same styles someone just puts a different take on it."
It's why she strives to offer customers as much choice as possible - stocking 25 labels including Gerry Weber, Verge, Jet Blonde, Scarlet and David Pond.
Her stores cater for busy women who don't want to forgo style in the process of being mum, businesswoman, wife and weekender.
Working on the shop floor means Hilary always has her finger on the pulse of what people want, and how they'll be wearing it.
"When I go buying I have to individually buy 25 times - although I may be looking at a range I see a bigger picture because I can't end up with 25 of the same thing.
"I also look for exclusivity, I don't buy what every other fashion shop has, we have got two exclusive German labels available in three boutiques, we also have a number of Australian labels that no one else stocks."
Quality is always at the top of her checklist so customers can be rest assured their clothing is not going to fall apart in an instant.
While she buys garments for all five locations, items are often shifted around to suit the lifestyles of local customers.
Each store has a different feel to avoid looking like a generic chain but you can always find the latest trends mixed with basics every woman needs in her wardrobe.
Those building blocks should include a well-fitted pair of black trousers, tailored black jacket, figure flattering pair of jeans, a quality pair of black boots and a handbag.
Having a simple capsule collection allows time-poor ladies to throw something together at last minute and still feel "put together".
If unsure of your style her staff are on hand to help choose garments or entire outfits - but Hilary says a woman's sharpest accessory is confidence.
"We have ladies shopping with us from Wellington and Auckland, who travel to shop with us because we have got the range and the experience," says Hilary.
"But I think as long as you feel comfortable and that it suits you it will look good."
Pointons Fashions celebrated 50 years in 2011 - two years after Hilary and husband Wayne bought out all five established stores.
Starting out as a drapery, the business was transformed to a fashion house by her parents, Glynn and Mary Pointon, who grew the empire from one site.
