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Style in the ‘50s: Sophistication Meets Rebellion

We look back at how life in the 1950s influenced the style of the Canadian man – and what Harry Rosen was up to at the time.

By: Harry Rosen StaffDate: 2024-09-03
  • man wearing a grey suit with buildings in background
  • man wearing a leather jacket with lake in background

In the middle of the 20th century, Canadian men dressed quite differently than they do today – that's no surprise – but some of the style elements have survived, making their way into the popular fashion of today.


We examine which of the ‘50s most prevalent styles are still alive in the modern age, plus delve into what was going on at Harry Rosen during the decade.



Mid-Century Sophistication


In the wake of World War II, an economic boom fueled a resurgence in traditional menswear. Tailored suits with wide lapels and high-waisted trousers, crisp dress shirts, and classic accessories like ties, pocket squares, and cufflinks defined the era. Men embraced a polished and sophisticated look, reflecting the optimism and stability of the times.


Today’s Take – refined, classic tailoring never goes out of style. Today's men channel this classic gentleman look and embrace timeless elegance with a few key pieces. Invest in a well-fitted suit, ideally in classic colours like navy, black or charcoal. Pair it with a crisp white tucked dress shirt and finish with a silk tie and a neatly folded pocket square.


Remember, being well dressed is all in the details—opt for quality cufflinks to add a touch of refinement to your ensemble. This look is perfect for formal occasions, formal office attire, or when you want to make a lasting impression.



Release Your Rebel


The rise of youth culture in the 1950s sparked a rebellion against traditional norms, giving birth to iconic subcultures like greasers and rockabillies. Leather jackets, denim jeans, and slicked-back hair became the defining sartorial expressions of this era, inspired by rebellious figures like James Dean or Marlon Brando in “The Wild One”. The look was all about attitude, confidence, and a touch of nonchalance.


Today’s Take – elements of this youthful spirit have returned today, including starting your look with a classic high quality white t-shirt—simple yet effortlessly cool. Pair it with a well-fitted pair of denim jeans, traditionally in a darker wash. Central to this look is the classic leather jacket, adding an edge to any outfit, completed with a pair of boots or sneakers.


This ensemble is perfect for casual outings, concerts, or any occasion where you want to exude effortless cool.



Modern Style, '50s Inspiration
Canada Goose Emerson Rubberized Logo Cotton T-Shirt

Canada Goose

Emerson Rubberized Logo Cotton T-Shirt

$195
Jacob Cohen Nick Cotton-Blend Stretch Jeans

Jacob Cohen

Nick Cotton-Blend Stretch Jeans

$565
Officine Creative Anatomia 013 Distressed Leather Lace-Up Boots

Officine Creative

Anatomia 013 Distressed Leather Lace-Up Boots

$895
Montblanc Horseshoe Buckle Leather Belt

Montblanc

Horseshoe Buckle Leather Belt

$485
Brunello Cucinelli Basic Fit Oxford Cotton Button-Down Shirt

Brunello Cucinelli

Basic Fit Oxford Cotton Button-Down Shirt

$870
Brunello Cucinelli Padded Leather Flight Jacket

Brunello Cucinelli

Padded Leather Flight Jacket

$11495
Brunello Cucinelli Essential Cotton Jersey T-Shirt

Brunello Cucinelli

Essential Cotton Jersey T-Shirt

$430
Ferragamo Fermin Polished Leather Oxfords

Ferragamo

Fermin Polished Leather Oxfords

$1210
TOM FORD Tonal Polka Dot Silk Tie

TOM FORD

Tonal Polka Dot Silk Tie

$420
Zegna Trofeo Wool Sartorial Mélange Suit

Zegna

Trofeo Wool Sartorial Mélange Suit

$5100
BOSS Slim-Fit Virgin Wool Serge Sport Jacket

BOSS

Slim-Fit Virgin Wool Serge Sport Jacket

$899


What Was Happening at Harry’s?


On February 4th, 1954, a young man named Harry Rosen along with his brother Lou opened up Harry’s first namesake menswear store on Parliament Street in the residential neighbourhood of Cabbagetown in Toronto with a $500 loan.


The first Harry Rosen store began selling made-to-measure tailoring to men, earning their business, confidence, and loyalty one by one, customer by customer. Harry and Lou even went as far as to bolt yards of fabric to empty boxes, stuffing them on their shelves to make their inventory look fuller.


After a few years of successfully developing a clientele, Harry and Lou hired their first ever employee, a bright-eyed 17-year-old by the name of Steve Pawlak, who, at the time of writing, is still our longest-serving employee and continues to work at our First Canadian Place store in Toronto’s bustling financial district.


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