For Your Inspiration: Sandra Pierce, aka The Bag Lady of Bay Street

If there’s one woman out there who does it all – this one has got to be it.

Some of you may know her as The Bag Lady of Bay Street, we witnessed her be referred to as the “Unofficial Mayor of Toronto,” but most consistently she is Sandra Pierce, woman-extraordinaire. We met her for lunch one August afternoon, and based on the fact that she showed up wielding a gorgeous black cane and sporting red enamel circle frames, our expectations were appropriately set quite high.

Sandra coined “Bag Lady Syndrome,” which is when a woman fears that she won’t have enough money saved for retirement, no matter how successful and financially responsible she is. And Sandra knows a thing or two about financial stability, seeing as how she is one of the top Investment Portfolio Managers in Toronto. We spoke about this, The Power of the Purse – a charitable evening that raises funds and awareness of the power of women and girls in the developing world – and fashion in a candid, no holds barred interview over lunch at the Hazelton in midtown Toronto. Ladies (and gents), take notes.

sandrapierce_2We asked Sandra, as the official Bag Lady of Bay Street, why she thinks successful women, even those who run their own businesses and are Birkin-Bag-successful, have anxieties about their financial stability. She basically summed it up as the unknown being f***ing scary. It’s difficult to answer those tough questions like, “will I have enough money to support the lifestyle I’ve earned?” And, “will I have enough money left over to retire?” “What even is, “enough”?” Sandra assured us that these are difficult questions to answer for anyone whose profession doesn’t require them to do so.

The answer?

“Don’t worry about the future – prepare for it. I always think a woman should be involved in the finances, and I’m not talking about the household budget because most women actually run the household finances. I’m talking about the investable assets. That while you make your money, you’re saving it to have a lifestyle that you’re going to enjoy. Money is just energy to provide you with something else, as opposed to a goal in itself. And I think women have to be involved with that and not be afraid to ask questions. I’ve never had a man say to me, ‘I’m not good at that.’”

We couldn’t help but ask Sandra how she would choose to enjoy her success, which for us obviously translates to, what is your dream purse. “A red Birkin. I love the history of it, the masterpiece of it, the craftsmanship. But I hope my husband doesn’t read this because he would say, if you didn’t buy those other 40 bags, you could have one!”

It is therefore only fitting that the pride and joy of Sandra Pierce is The Power of the Purse, a spectacular event dedicated to and full of influential women that she built from the ground up. She admit to us that she doubted her ability to create an event like this, but unsurprisingly to us, she’s pulled it off seamlessly for seven years, raising over $900,000 (!) for Plan Canada’s Because I am a Girl global initiative. We asked her why “The Purse” and she put it so plainly, so matter-of-fact: “Women have more power in their purse than ever before to make a difference. That’s truly what it is.”

Two hours later, we’re officially obsessed and nearing the end of our time with Sandra, and just had to ask her about her style, go-tos for a desert island, and the lessons she’s learned. See Q&A below.

H: What are three wardrobe essentials every working woman should have?

S: A good watch, a great pair of shoes, and one outfit that makes you feel like a queen.

H: What are the three designers you have the most of in your closet?

S: Nicholas Kirkwood for shoes, Chanel for bags, and Balmain for clothes.

H: You’re stranded on a desert island – what five things would you want with you?

S: A big juicy book, rosé champagne, a pillow, an Hermès blanket, and Ryan Gosling.” (We had to stop ourselves from applauding.)

H: If you could do-over one thing, what would it be?

S: I don’t really believe in regrets, but I would worry less. I spent a lot of time and energy as a young woman worrying, and it actually does all work out.

H: What would you say to your 20-year-old self?

S: Wash that man right out of your hair. And don’t let them define you – find your own definition.

H: And lastly, who is your icon?

S: Iris Apfel. One, I love her I-don’t-give-a-shit attitude. I love her style, I love that at 96 she takes time and effort to pull herself together every day. And she doesn’t edit herself, either. I’ve been in front of her when she’s spoken in a small group and she just tells it like it is. I love the fact that she is truly herself.

Needless to say, here at Handled we are confident in who our icon is. And it ain’t Iris.