By Dalia Sefton
Edited by Justine Pelland-Dyke
Bob Dylan once famously sang, “You don’t need a weatherman to know which way the wind blows.”

Well, Bob, the wind is blowing at a crisp five degrees Celsius, and judging by the apocalyptic results on my weather app, a hard rain’s a-gonna fall. So, while I appreciate the poetry, I’m going to need a little more guidance on what to wear.
Every October, Montreal residents instinctively shove their hands deep into their pockets, bury their faces in their scarves, staring at the frigid pavement and wishing the sun would make a guest appearance. This may seem like an inherent part of being a Montrealer, but I would argue it is nothing more than the borrowed mannerisms of folk’s fall fashion icon, Mr. Robert Zimmerman. You may know him better as Bob Dylan, the man who told us long ago exactly what we’re supposed to wear in the fall.



For this particular curated wardrobe, we look back to late 1960s Greenwich Village, a time when artifacts like Levi’s 551s and boxy brown velvet jackets ruled the sidewalks. Today, the folk revival and its bohemian lifestyle are making a comeback on the streets of the 514. There is no question our generation has a habit of making things, for lack of a better phrase, great again. As each season comes along, Gen Z cannibalizes countercultural movements to the point that resurrecting history’s greatest fashion hits has become something of our own zeitgeist. Perhaps we should have seen this coming after being beaten over the head with clean girls, microtrends, coastal grandmother core, matching sets and the horrors of quiet luxury. Something in us must have snapped. We spent too long chasing business casual chic, and the time had come for a revolt. The pendulum has now swung in the opposite direction, as pendulums tend to do when civilization has had enough.
That is when the Dylan look came stumbling in, not that it ever really left. The man has been lurking in the corners of American fashion for over sixty years, hiding behind the combination of bootcut jeans and Blundstones, waiting patiently for the rest of us to catch up. Long before we called it vintage, Americana, bohemian or whatever tortured name TikTok has invented this week, Dylan was already wearing it. Now half the city is walking around dressed like they have things to say, places to be and a bluesy “yeah, man” ready to slur.
Blowin’ in the Wind
With A Complete Unknown, Timothée Chalamet, already a fashion icon in his own right, showed us just how versatile and trendy Bob’s wardrobe really is. Copying Dylan’s blond era may not have been Timothée’s best look, but his many nods to ’80s double-breasted suits won the public’s approval. Hedi Slimane also understood the assignment. In his final collection for Saint Laurent in 2016, the French designer practically dragged the Dylan uniform straight onto the runway, showcasing the rock and roll tailoring that defined his era at the house. Albums came and went, eras rose and fell, but Dylan’s look stayed stubbornly the same.

Don’t Think Twice, It’s All Right
From Timothée Chalamet to Heath Ledger, Christian Bale, Richard Gere and my personal favourite, Cate Blanchett, Bob Dylan has been portrayed by an endless lineup of Hollywood stars, proving he simply cannot escape the spotlight. He embodies everything we love most about fall: worn-in denim, brown suede, leather boots and Gen Z’s fan favourite, the general look of nonchalance. Whether he wanted the honour or not (if I had to guess, the latter), Dylan’s wardrobe has become the unofficial dress code of this season.



