Name and occupation?
Alison Gordon. I’m the CEO of 48North.

What does your day-to-day look like at work?
I’m on a plane a lot, I’m in meetings a lot, I’m on the phone a lot, I’m doing photoshoots. And I’ve got the farm.

Does your company and/or industry have a dress code?
No. We’re in cannabis, so there’s something slightly funky. But we’re also a public company, so there’s a level of professionalism, but everybody just kind of does their own thing.

Kayla Rocca

What do you wear to work?
It really depends on what’s going on that day, so I always check my calendar in the morning. Like, do I need to look nice today? If I have no external meetings, I’m generally in a nice boot, coloured jeans and a funky top of some kind. If I’m in external meetings or meeting with bankers or investors, I’m generally wearing dresses or more “business” stuff, but I try to keep it funky just because that’s me, and I gotta be me. And then on the farm, it’s really just jeans, T-shirts, stretch pants…. The farm is the best – you can wear whatever you want.

My Alice and Olivia leopard print dress, we’ll say it’s my raising-money dress or my “I’m serious” dress. It’s a good dress when I’m meeting with investors and bankers because it stands out. It’s long and has long sleeves, so it’s not too crazy. My longer G.label pants with the Veronica Beard blazer are good if I’m presenting, which I often am, at a conference or something or even just on days when I have a lot of meetings.

It’s very hard for me to get dressed most days because as a woman CEO, when I walk into a room it’s generally men – the investors, the bankers. I don’t read “CEO” when I walk into a room, so my clothes need to communicate my leadership, my professionalism and my strength. At the same time, it’s a cannabis company, so I also need to show an edgier side. But I have to be conscious about drawing a line at body-conscious clothes. I have a lot to think about as I get dressed every day.

I don't read “CEO” when I walk into a room, so my clothes need to communicate my leadership, my professionalism and my strength.

And I feel like nobody talks about the fact that female CEOs need a clothing allowance because people comment when I’m doing media – like, “Oh, didn’t she wear that dress another time she was on?” There are investor boards that are always like “She’s worn that dress before!” It’s like, “You’d never say that about a guy!”

Kayla Rocca

How do you shop for clothes?
I shop a lot online – especially when I’m in the States because it’s easier there. I’ll often order to the hotel. It’s a running joke with my boyfriend that every time we go to a hotel, there’s a massive box from Shopbop waiting for me. I order from there a lot because I don’t have time to shop – it’s really easy. I’ll go online and start filling a cart – sometimes I don’t buy any of it and sometimes I’m like, “Oh, there are some things that I need,” so I go through the cart and take out half of it.

Do you work with a stylist?
No, I’m happy with my own style.

What inspires your style?
Well, I love the ’70s and that whole glam rock. Also Paige Matheson, a character on Knots Landing in the ’80s and ’90s who always wore short suits. She was a businesswoman.

Kayla Rocca

Are there any other challenges you have when it comes to getting dressed?
There’s an expectation for a woman to look a certain way, and some days you’re just not feeling it. And it’s just not the same as a man being able to throw on a suit and, like, grab a funky tie – no one’s noticing if that suit is the same [as one he’s worn before]. So, there are those days when I’m like, “Why can’t I just throw on whatever I want?

Nobody talks about the fact that female CEOs need a clothing allowance.

Is there anything that you bought and then were like, “This just doesn’t work for me”?
I’m always trying to wear medium-length shift dresses that are more boxy, but then they just sit in the closet.

Is there anything else you want to say about your style or how you dress?
A huge thing when you’re running a business, especially in the cannabis industry, is differentiating the company and, if you can, differentiating yourself. When you’re networking, I think people are more likely to remember you when you stand out. So, if you dress the same as everybody else, that’s not going to help the cause – you can be an individual and still look professional.

Alive and Olivia Delora Fitted Mock Neck Midi Dress ($450)


Veronica Beard Brock Dickey Checked Wool-Blend Blazer ($417)


G. Label Kelly Wide-Leg Trousers ($695)