3 Ways to Wear the Over-the-Knee Boot

The hottest boot of the year is the stretch suede design that laces up behind the knee. Designer Stuart Weitzman kicked off the trend last year when I bought mine. Almost everyone I worked with at Holt Renfrew’s head office owned a pair – either the flat Lowland or the heel Highland – they are that comfortable! 


The black suede Highland, shown here, is the most versatile boot I’ve ever owned. It goes from day to night, work to weekend, and the soft stretchy suede is truly comfortable. I never buy anything that I can’t wear less than 3 different ways – these boots can be worn so many different ways that you’ll reach for them all season.  

Weekend shopping – I’m always running around on the weekend so here, I’ve paired the boots with an oversized black sweater, mini skirt and Givenchy cross-body bag. Bonus – they’re warm too so you can wear a mini in the winter with tights and not freeze. 


Work – For an office look, I paired the boots with a stretch denim pencil skirt and the cosiest Eileen Fisher cardigan. I’ve also worn my boots with a black dress and tailored jacket for a boardroom-worthy look. 


Out with the girls – This Tanya Taylor tunic came with a matching skirt but I liked it better with tights and the over-the-knee boots. It’s a little short but who cares. 

Makeup, Lace Maralit. Hair, Tony Masciangelo and Jed Puznak, Alcorn Hair. Photography, Tara West. 


Here’s a repeat of the last look. I wore the outfit when I was interviewing designer Tanya Taylor at Holt Renfrew before one of her trunk shows. I love Tanya’s energy and her designs just keep getting better!