When Roots called last week and asked me to show how I would wear Roots on a date, I had a slight panic attack. Roots, on a date? Is that even possible? Where am I going on said date, the woods!? At first I thought I would try and style myself in head-to-toe Roots, and create an outfit for a make believe date of ice skating and hot chocolate (i.e. my worst idea of a date ever) but that wouldn’t be what I would really wear, would it?  As I looked through their site more closely, I found some key pieces that reflected staples of my wardrobe that I had, in fact, worn on a date just a few days before.

It was a Monday night at Parkdale’s newest hot spot: Grand Electric. Since it was an early-in-the-week restaurant date, I wanted my outfit to be laid back, stylish (obviously), a bit sexy and also warm because it was fa-fa-fa-reezing that night! So I slipped into a skin tight long-sleeve black maxi dress and paired it with a sleeveless leather vest. I am a sucker for the motorcycle style, and Roots’ Deeva vest has the most amazing cut, made from incredibly supple  Italian leather. Style and warmth, I love it. Next, a classic heather grey hoody layered underneath my leather jacket and vintage mink vest. I’ve had a bit of an extreme obsession with hoodies since my younger days as a, er, “skater girl” (yup, really), and the classic hoody is still a staple of my style to this day. Since my ex-boyf decided to keep my favourite American Apparel hoodie when we split, I’ve been in search of a new alternative and I love that this classic style from Roots is made from organic cotton. Last but not least, the Annie Oakley bucket bag from their Vintage Tribe collection, I don’t know what to say about this one except for the fact that it is the coolest bag I have ever seen from Roots and I am OBSESSED!

What I Wore: Roots Deeva Vest $448, Roots Classic Full Zip Hoodie $76, Roots Annie Oakley Bag $288, Designers Remix Black Maxi Dress from 290 ION, Black Motorcycle Jacket from London, Vintage Mink Vest, Black Toque (gift), Filippa K boots from George & Jane.

All What I Wore images by David Gillespie 

 Hair by Ronnie at SheShe Beauty