The Guy’s Guide to Dressing in Layers

With colder seasons just around the corner, closet strategies are slowly being updated to dress accordingly. That means dressing in layers; a sure fire way to stay warm and still look like an ace.

“I’m one of those guys who gets excited when the weather starts to cool,” says Harry Rosen’s Managing Director, Michael Peters. “For me it signals a time to revisit some of my favourite pieces. I always advise to keep in mind the three F’s –fit, fabric, and function.”

But chances are you may look at layers like somewhat of a fashion rubik’s cube? “Wait, so does the jean jacket go over the sweater, but under the vest?” you ask. Here are a few notes to make things more convenient.


According to Peters, this layer is the initial inner item that will be touching your skin, so you want to make sure that it’s not only breathable but also non-irritating. We’re thinking of a high quality cotton undershirt.

“As a general rule, start with the thinnest clothes. Each layer should hug the body,” says Peters.

Layer 1

Classic V-Neck, Ralph Lauren, Three Pack ($38.50)


Building upon that, a nice button down tailored shirt is most often a successful option. Peters advises to choose a shirt that doesn’t contain a wild pattern, as it will be hard to complement. Opt for something neutral with a solid colour, to anchor the outfit.

“Your fabrics should be complementary and not fight each other,” says Peters.

Layer 2

HUGO BOSS, Cotton Dress Shirt ($185.00)


 The third layer or middle layer as it might be referred to, tends to be a prime opportunity for throwing on a premium quality thin v-neck sweater. Note; remember that you want it to be closely hugging your body like a pair of slim cut jeans.

Layer 3

Silk Cotton Cashmere Vee Pullover ($85.00)


Now, we’re not here telling you that you should be one of those fashionisto marvels who walk down the street wearing more layers than an onion. So the forth and arguably the final layer, is where you’ll package the look with a finishing cover. Maybe it’s a tweed blazer, a chunky wool cardigan, a jean jacket – but no matter what, Peters calls for texture.

“It’s important to keep in mind,” says Peters. “You want to mix in a variety of rich textures so I’ll often wear a wool tie to add another dimension. To complete the look, a wool or tweed sports jacket is the ideal outer layer.”

Armani Collezioni, Unstructured Jacket ($1,325.00)

Layer 4


We understand that you don’t always want to sacrifice comfort for style, so when the temperature really starts dropping, it might be necessary to replace that fourth layer with an actual cold weather jacket – we’re talking about a bulky, yet silhouette defining winter parka.

Layer 5


Canada Goose, Banff Parka ($845.00)

Jeremy Singer is a freelance writer and reporter from Toronto. He has a journalism degree from Ryerson University, and enjoys covering all aspects of men’s lifestyle and pop culture. He hopes to one day try on an $8,000 suit but not buy it, because he’s afraid of commitment. Feel free to contact him on Twitter or at his website.


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