Man Repeller's Leandra Medine shares her cold-weather styling tips for Canadians

Founder of the popular website Man Repeller, author, and, more recently, footwear designer Leandra Medine is a bona fide trendsetter and fashion authority who's been named to Forbes' flagship "Top 30 Under 30" list, won a blogging award from TIME, and sits front row at all the international fashion weeks. She has over 2.5 million followers across her personal and brand accounts on Instagram, all of whom can't get enough of her bold sartorial choices and open, often humourous approach to style.

In Toronto earlier this week for a special appearance at Hudson's Bay Style Social shopping event downtown — Medine's eponymous shoe line just launched exclusively in Canada at the department store — Medine sat down with us to talk about why we all need a navy parka, whether socks with heels are still a "thing",  and her top cold-weather styling tips for us fashion-conscious, cold-braving Canadians everywhere. 

What are your favourite outerwear trends this season?

I haven't really thought much about outerwear yet, but I always come back to ankle length swing coats. I think I'd like a checkered coat with a hood for the season. I'm not as keen on the puffer coats, although I very much appreciate their value and definitely wear them when it is required, and there are actually really good iterations of really fun ones that are coming out. It's probably great to live in Canada right now, because outerwear feels more innovative than it has in a long time.

Can you tell us the three essential pieces in your coat wardrobe for fall?

I've got that long coat with a hood, and then I have a plain black wool coat that sort of goes with everything, it's like an end-all be-all to some degree, and a cropped puffer that I tend to like to wear with heels because for whatever reason the long coats feel too fancy when I'm dressed fancy. So, that offers a nice contrast.

Many people end up investing in a durable, but plain, black winter coat—what are some stylish ways to dress up a black parka?

The really simple way to dress up a black parka is actually to buy a navy parka. There's something really regal about that colour and it seems like we always gravitate towards black, but there is so much opportunity with brown and navy. Black feels like it matches with everything under the sun, but I think you can make that true for brown or navy also.

What are your favourite cold-weather layering tips?

For actually staying warm, I kind of just keep adding on. It starts with a bodysuit, and then there's a short sleeve t-shirt, and then there's a long sleeve t-shirt, and then there's a sweater, and then there's a jacket; or sometimes, there's a long sleeve shirt, which could be a turtleneck, and then a button down over it, and then a cardigan over that...and therefore you see all the layers and they're part of this deliberate look. There is a lot more opportunity to express yourself when there are multiple layers involved, because you can also shed these parts of yourself through the course of the day, which is really nice. And metaphoric.

Are socks with heels still a trend?

Whether or not I'm over it does not command its trendiness. But I like to subscribe to that trend; it feels like a really easy way to take summer shoes into the winter with you, or to justify the purchase of a pair of sandals in the middle of the winter, which sometimes you kind of just need to do to make yourself feel better about how cold you are.

Tell us about your shoe collection.

The collection is really split up into two disparate ideas. The first being, everyone who has what is presumably deemed a wardrobe staple — so jeans, white t-shirts, black jackets — should be able to feel like they're in a proper look with just the inclusion of a new pair of shoes. I've always lived by this tenet that you don't need to buy new clothes in order to feel like your wardrobe is being updated, that your accessories can really say more than maybe we let on to. That's really one of the founding principles of the shoe brand.

And then on the other end of it, if it's not these shoes that are supposed to be the whole outfit, they are these shoes that are supposed to make you feel like second skin, the things that you come back to season after season that are interesting enough to elicit that sense of exciting, indulgent impulse purchase, but that don't feel dated after the sum of the season.

For more from Leandra, including the three things she does when she wakes up and just how many shoes she may own, check out our rapid fire round with her below.

Life with Leandra Medine — A tell-all in 13 questions:

The first 3 things you do when you wake each weekday morning:

Drink a bottle of water, brush my teeth, go to my girls' room.

What do you tell yourself when you need motivation?

So many things. This is like an ongoing monologue at all parts of the day. What do I tell myself when I need motivation, what do I most frequently tell myself: I've been through worse, and I'll get through this.

One book you'd recommend to everyone?

I don't think there's a one-size-fits-all with books. That's really hard. But if you're looking for a light read, I would recommend Me Talk Pretty One Day by David Sedaris. It's an enjoyable way to escape from perhaps the banalities of your day, or the dread of your day.

Favourite motherhood moment so far!

Every moment has been wonderful. Just the fact that they're healthy is enough for me.

You have an entire weekend to binge-watch stuff — what's it gonna be?

The only time that's happened in my life has been around a personal tragedy to some degree, and I watched three entire seasons of Friends, and I don't regret it. So maybe I would do that again.

What is your favourite restaurant in the world?

My own kitchen because that's where the most diverse food comes out.

What's your poison?

My favourite drink is definitely a cappuccino made with oat milk.

What's your desert island beauty product?

Red lipstick.

How many pairs of shoes do you own, approximately?

I like shoes very much. Probably to the sound of 170 pairs.

Best (romantic) relationship advice you could give:

Don't underestimate the power of ease.

Current, or lifelong, role model and why?

I want to say that it's somebody like Maya Angelou. And I'm still trying to figure out who my "role model" is, but I have this vision in my head of a very confident version of myself who's just meditating on top of her own uterus, like sitting on a cushion that looks like her uterus. I'm not that person yet, but I really want to be that person. And I think she's my role model.

Secret internet obsession!

It's not such a secret, but probably astrology sites. I'm always looking for them to tell me things about myself.

The best compliment you've ever received:

Probably anything related to intelligence like "that was a really smart take" or "an enjoyable read." Those are the best compliments from a vanity perspective. The best compliments morally have all been related to "your sharing saved me," "helped me," "made me want to share," "it healed my loss."

Truc Nguyen is a Toronto-based writer, editor and stylist. Follow her at @trucnguyen.