When you think of classic style and timeless pieces, there’s a good chance that Roots comes to mind—and for good reason. In 2023, the homegrown brand is celebrating 50 years of effortless style. Its enduring approach? Designing pieces that are meant to stand the test of time, both from a sartorial perspective and a sustainable one. Its use of high quality fabrics made from organic and recycled materials means that those pieces are set to be worn for years to come. Here are five of our favourite Roots style staples, all offering comfort and versatility in spades. It’s your Roots, your way.

Oxford Relaxed Shirt


An oversized Oxford shirt is a capsule-wardrobe classic, no matter your style leanings. Roots’ bestselling version—made with 100 percent organic brushed cotton for a super-soft feel—is primed to expand your closet potential. It’s designed with the perfect oversized fit, so you can wear it open over a tee or buttoned-up and loosely tucked.

Price: $88


Re-Issue 76 English Saddle


No one does leather like Roots, and this English Saddle reissue is proof. Inspired by an iconic bag released by the brand back in 1976, it’s been refreshed and recreated for the modern day in Roots’ Toronto factory. Check the equestrian-style shape and contrasting topstitching—perfect for this season’s prep trend.

Price: $398


Rossland Check Blazer


Whether you’re on the clock or very much off, a relaxed-fit blazer remains one of the most instantly elevating pieces you can have in your closet—which is exactly why we love the Rossland Check Blazer, with its structured design and standout houndstooth weave. Make it a whole look with the matching pleated trouser, or keep it simple with your go-to jeans.

Price: $148


Dauphin Pleated Pant


Looking for an easy trouser that does double duty from a.m. to p.m.? Meet the Dauphin Pleated Pant. Its beauty is all in the thoughtful design: It’s cut from a soft yet structured cotton twill and has a flattering wide leg that tapers at the ankle. Boardroom to cinq-à-sept never looked so chic.

Price: $108


Original Organic Relaxed Full Zip Hoodie


A zip hoodie is a forever fall essential in our books. This forest-hued one—made in a soft fleece with a modern relaxed fit—lets you switch up your look with ease. Sport it casually over a tank and jeans for weekend errands, or double up with the matching sweatpants to really lean into the cozy autumn vibes.

Price: $98