Stroll Through 70 Years of Style at Harry Rosen

Harry Rosen & SHARP

Harry Rosen’s 70-year history tells a story of sartorial evolution, one that has reflected and shaped the clientele of each era. What began as a humble store in Toronto quickly transformed into a brand synonymous with luxury, craftsmanship, and personal service. From the glitter-dusted floral prints of the 1970s to casual comforts brought on by the turn of the millennium, Harry Rosen has a history of meeting the culture head-on, offering refined yet exciting selections for discerning shoppers of every decade. To commemorate the menswear champion’s seven decades of success, we thought it was a fitting time to dive into the heritage of Harry Rosen. Cruising through seventy years of style yields more than just nostalgia, though — we also discover how Harry Rosen reinterprets trends from every decade, styling each one to deliver a fresh and fashionable take for today.

1950s: The Rise of Youth Culture

Today, teenagers leave their fingerprints all over the modern market, from meme-able social media marketing to Spotify’s overflowing selection of teen-pop. It’s easy to think of the teenager as a de facto category — especially in the identity-shaping world of fashion — but, before the 1950s, adolescents were more of an afterthought. It wasn’t until the mid-20th century that youth employment spiked, brought on by a boom of post-war prosperity. Flush with cash, teenagers rocked and rolled their way into the market, popularizing slamming guitars and blue jeans — and setting a precedent for brands to capture the young customer.

Harry Rosen, founded in 1954, was in the same boat — fresh, disruptive, and eager to make its mark. While known for tailored suits, the Canadian menswear titan kept an eye on the emerging subculture, embracing the rebellious, rugged-casual looks that upended sartorial tradition. The leather jacket, jeans, and white t-shirt combo — popularized by mid-century celebs like James Dean — became a symbol of nonconformity. Today, Harry Rosen continues to balance well-crafted garments with casual, wear-able trends, offering an elevated take on the youthful aesthetic.

1960s: The Mod Scene

Although we’re knee-deep into the 2020s, mid-century modern has endured, carving out a sizeable niche in today’s interior design, grooming, and fashion. In the 1960s, though, mid-century modern was simply… modern. Slick tailoring, rich hues, and shaggy haircuts defined the Mod movement. This style revolution struck a chord at Harry Rosen; in the decades since, the retailer has doubled down on slim-cut suits, sharp silhouettes, and bold accessories. Today’s modern, fitted looks appeal to a generation looking to make a statement. Styles of the decade return today in sleek tailored jackets, crisp shirts, and clean lines.

1970s: Disco Fever

An explosion of flamboyant ‘fits lit up the 1970s sartorial scene, casting a burnt orange glow over every garment rack. Flared trousers and wide-collared shirts embody the era’s carefree confidence, coupled with disco-funk anthems and plenty of patterns. Saturday Night Fever style and Harry Rosen’s trademark tailoring merge here, manifesting in this white Tom Ford suit — a statement piece to shake up the refined wardrobes of Harry Rosen shoppers. Discerning customers can dance back to the decade with this high-quality fabric and iconic silhouette.

1980s: The Bomber Jacket Boom

Though less radical than their leisure-suit-loving predecessor, the 1980s were far from subdued. Instead of flamboyant prints and flared trousers, however, ’80s style embraced the daring, edgy appeal of bomber jackets and flashy accessories. Inspired by military wear but quickly adopted by the fashion world, the bomber’s versatility and cool factor made it a must-have. Harry Rosen responded to this shift by curating collections that mix luxury with laid-back vibes. Today, a casual staple like the bomber jacket can be found with trendy details like a large hood and asymmetrical pockets, in premium leather or other high-end fabrics, appealing to both the fashion-forward and the classic dresser.

1990s: The External Tuxedo

In the ‘90s, tuxedos stripped down to their essentials. Clean lines, neutral tones, and precise tailoring took centre stage, pushing aside the boldness of the ‘80s to make room for a new, understated type of elegance. It’s a trend that endures — think of today’s sharp fits, boasting sleek lapels (shawl or peak) and flat-front trousers in timeless black. Harry Rosen’s expertise in tailoring empowers clients through a sophisticated take on this classic style, as showcased in the timeless Ralph Lauren Purple Label Tuxedo above. Paired with a crisp white shirt and finished with shiny leather loafers, it speaks to the everlasting appeal of minimalism.

2000s: The Rise of Athleisure

Thanks to recent revivals of Y2K-inspired clothing in designer capsules and collections, fashion from the early aughts is still fresh in the collective consciousness. The era took ‘dressing-down’ to new heights, infusing a healthy dose of athleisure into everyday street style. Characterized by luxury tracksuits, sleek sneakers, and performance fabrics, athleisure became a go-to for suave comfort-seekers. This coincided with an expansion at Harry Rosen, where their product selection now includes a range of high-end spins on casual pieces. The trend rejuvenated menswear, proving that even casual, sporty pieces could carry the same level of craftsmanship and style as a tailored suit.

2010s: Stay Warm in Style

Given the country’s famously freezing temperatures, Canadian clothing brands were uniquely positioned to succeed in functional fashion. When brands like Moncler, Canada Goose, and Mackage brought about the rise of stylish outerwear, Harry Rosen swooped in to curate an upscale selection of overcoats and puffer jackets. Once reserved for winter sports, puffer jackets became a must-have for urban fashionistas, with Harry Rosen as the go-to destination for high-quality puffers that combine luxury with practicality. These jackets, featuring cutting-edge insulation and sleek designs, are now an essential part of men’s wardrobes, offering both comfort and style during the colder months.

2020s: Quiet Luxury

Quiet luxury emerged in response to an overload of maximalist micro-trends, favouring long-term investments over bold logos and flashy fast fashion. Today’s fashion-conscious men seek understated elegance — luxury that speaks softly, but with authority. It’s natural, then, that Harry Rosen became an emblem of quiet luxury, as the Canadian retailer has long championed this approach. Attention to detail and craftsmanship reflects a focus on quality and fit, lending a subtle sophistication to every garment. In this era, brands like Tom Ford, Brunello Cucinelli, and Ralph Lauren have gained prominence at Harry Rosen, reflecting the modern man’s desire for timeless, investment-worthy fashion over transient trends.

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