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A Decade of Men's Fashion: Tracing the Evolution of Street Style

Diane von Fürstenberg
By Diane von Fürstenberg
·5 min read
This article takes a retrospective look at the dynamic world of men's street style over the last ten years, offering insights into how fashion trends and the industry itself have transformed. Through a series of memorable snapshots from various global fashion weeks, it showcases the enduring and evolving personal styles that define the menswear landscape.

Fashion's Shifting Sands: A Ten-Year Journey Through Men's Street Style

A Look Back at the Landscape of Men's Fashion Weeks

Ten years ago, the scene at men's fashion shows was markedly different from today. We journey back to the spring 2017 menswear season, exploring the sartorial choices of stylish attendees. Over this period, significant changes have reshaped the industry, including a major reshuffling of creative directors at various design houses and a noticeable shift in men's fashion silhouettes, which have recently become more relaxed. Furthermore, the global footprint of menswear weeks has contracted, moving from four major fashion capitals plus Pitti Uomo in Florence, to primarily focusing on Milan, Paris, and Pitti.

Notable Personalities and Enduring Styles

The past decade has witnessed both profound losses and remarkable continuities within the fashion world. The industry mourns the passing of Virgil Abloh, whose influence remains deeply felt. Alessandro Michele's departure from Gucci for Valentino in Rome marked another significant transition. Despite these changes, some elements remain constant: Matthew Foley, for instance, has maintained his signature bleached blond hair, although his style has evolved from Milanese sprezzatura to Thom Browne's distinctive gray flannel suits. Iconic figures like Yu Masui and Takeji Hirakawa continue to make their presence known, while photographers Phil Oh and Acielle Tanbetova consistently capture the vibrant off-the-runway fashion scene.

A Journey Through Time: Style Reflections

Embark on a nostalgic trip down memory lane, examining the street styles that have stood the test of time and those that now appear dated. The rapid pace of fashion ensures that enjoying the journey is paramount.

Florence: World Cup Excitement at Pitti Uomo

Attendees at Pitti Uomo in Florence showcased their enthusiasm for the World Cup, mirroring the anticipated excitement for the spring 2027 season, especially with England's upcoming match against Croatia on the second day of the fair.

Milan: Alessandro Michele's Pre-Gucci Style

It's now rare to find a Phil Oh photograph of Alessandro Michele without his "Techno is my boyfriend" hat. However, a decade ago, the designer was deeply immersed in Gucci's aesthetic.

Paris: Public School's Upcoming Presentation

Dao-Yi Chow and Maxwell Osborne, the creative duo behind Public School, are set to host a special presentation in Paris from June 25th to 28th this season.

Paris: Matthew Foley's Style Transformation

In 2016, Matthew Foley's wardrobe was characterized by Emporio Armani, Moncler Gamme Bleu, and Converse. Today, he is more commonly seen in Thom Browne's skirt suits, though his bleach blond hair remains a consistent feature.

Paris: Mobolaji Dawodu's Timeless Aesthetic

Mobolaji Dawodu's unique personal style has remained remarkably consistent over the past ten years, proving to be a rare constant in an ever-changing fashion landscape.

Paris: Chitose Abe's Enduring Presence

Tokyo-based designer Chitose Abe continues to present her men's and women's Sacai collections in Paris, maintaining a strong presence in the global fashion scene.

New York: Miles Chamley-Watson's Dual Success

Steff Yotka predicted Miles Chamley-Watson's rise in 2016, noting his dual talents as an Olympic fencer and a model for brands like Rochambeau and Public School, and his participation in the Rio Olympics. Today, Watson is a beloved figure at Vogue, modeling for Vogue World events in Paris and Hollywood.

London: A$AP Rocky's Enduring Partnerships

A$AP Rocky, captured here leaving the JW Anderson show where he announced a collaboration, continues to maintain a close friendship with the designer. He has since become a prominent fixture at Dior events.

Paris: Dwayne Wade's Professional Transition

Just one month after this photo of Dwayne Wade was taken at Dior men, the basketball star signed a two-year contract with the Chicago Bulls, marking a significant career move.

London: The Allure of Dinosaur Accessories

At an off-site Coach show held at Lindley Hall, nearly every guest was seen sporting some form of dinosaur accessory, highlighting a playful trend.

Paris: Chloë Sevigny's Fashion Week Return?

Chloë Sevigny's last attendance at the menswear shows was for Kenzo's spring 2017 presentation. The question remains whether she will make a return this season.

Paris: The Unmissable Michele Lamy

No Paris Fashion Week is complete without a sighting of Michele Lamy, whose distinctive style is an integral part of the city's fashion scene.

Milan: The Enduring Appeal of Gucci

Street style enthusiasts continue to have a strong affinity for Gucci, a trend that has persisted over time.

Paris: Yoon Ambush at Louis Vuitton

Designer Yoon Ambush was spotted at the Louis Vuitton show, capturing a moment of her presence at a major fashion event.

Florence: Models in Posed Perfection

Models strike a pose for a photograph in Florence, adding to the visual narrative of the fashion week.

Paris: Supreme Soccer Jersey Trend

A stylish individual wears a Supreme soccer jersey in Paris, reflecting a trend that coincided with Japan hosting the 2016 FIFA World Cup.

New York: Rocky Xu's Entrepreneurial Journey

Before becoming the celebrated purveyor of New York City's beloved matcha at Rocky's Matcha in 2026, Rocky Xu was captured here in New York. His matcha is now a popular choice at fashion hotspots like Raf's and Happier Grocery.

Milan: JJ Martin's Brand Expansion

In 2016, La Double J by JJ Martin was a nascent online shopping destination. Today, the brand has evolved into a comprehensive lifestyle and fashion entity, frequently featured in prominent publications like Vogue and Architectural Digest.

Paris: Marc Goehring's Faith Connexion Ensemble

Marc Goehring is seen in Paris sporting Faith Connexion pants, showcasing a specific fashion choice at the time.

New York: Hanne Gaby Odiele's Effortless Style

Hanne Gaby Odiele exudes effortless off-duty style in New York City, demonstrating a chic and relaxed aesthetic.

Milan: Gilda Ambrosio's Consistent Appeal

Gilda Ambrosio continues to be a favorite subject for Phil Oh, a testament to her enduring and captivating style.

Paris: Luka Sabbat's Timeless Cool

Ten years on, Luka Sabbat retains his status as a fashion-forward individual, maintaining his cool presence.

New York: Isaac Miller's Digital Transformation

Today, Isaac Miller is recognized for his popular TikTok account, @isaaclikes_, where he interviews celebrities, designers, and influencers about their preferred global restaurants and destinations. This marks a shift from his earlier presence at fashion events.

New York: Noah Johnson's Trendsetting Years

Before assuming his role as Highsnobiety's Editor in Chief, Noah Johnson served as GQ's Global Style Director, a position that involved identifying and documenting emerging trends.

Paris: The Appeal of Specific Fashion Pieces

The desire for these shorts and a "Never Trust a Vogue Girl" shirt from Hood By Air was palpable, indicating popular fashion items.

Paris: Jonas Glöer's Prada Loyalty

Jonas Glöer, a model and friend of Raf Simons, was an early adopter of Prada, sporting the brand long before Simons joined the Italian fashion house.

Milan: Fendi's Unified Show under Maria Grazia Chiuri

By 2026, under the creative direction of Maria Grazia Chiuri, Fendi will be showcasing its men's and women's collections together in a unified presentation.

Paris: Caroline de Maigret's Chanel Devotion

Caroline de Maigret has consistently been a loyal supporter of Chanel, reflecting her long-standing relationship with the luxury brand.

Paris: Takeji Hirakawa's Signature Style

Takeji Hirakawa remains a beloved figure in menswear fashion, known for his distinctive style, even when he opts for repeated outfits, as noted by Vogue's Nicole Phelps in 2023.

Paris: Yu Masui's Irreverent Approach to Fashion

Yu Masui, a Japanese journalist, is celebrated for his playful and unconventional approach to dressing, consistently earning a spot on "Best of the Year" lists, as observed by Vogue's Nicole Phelps in 2023.

Milan: Will Welch's New Chapter

The spring 2027 menswear season will mark Will Welch's first as a non-GQ editor, embarking on a new role under Pharrell Williams, indicating a significant career shift.

Milan: Natasa Cagalj's Influence at Ports 1961

After Natasa Cagalj, a Central Saint Martins graduate, was appointed creative director of Ports 1961 in 2015, Milan's streets quickly became adorned with vibrant tassel skirts, a testament to her immediate impact on trends.

Milan: Moschino's Star-Studded Menswear Show

Moschino's spring 2017 menswear show featured an impressive lineup of models, including Miranda Kerr, Stella Maxwell, Taylor Hill, and a then 19-year-old Hailey Baldwin.

Florence: Jenny Walton's Presence at Pitti Uomo

Jenny Walton was captured at Pitti Uomo in Florence, highlighting her attendance at the prestigious event.

New York: Models on Skateboards

During New York's menswear week, models were seen utilizing skateboards for transportation between shows, showcasing a youthful and dynamic aspect of the event.

New York: Jenna Lyons's Leadership at J.Crew

Jenna Lyons, at the time, held the position of executive creative director at J.Crew, playing a key role in shaping the brand's aesthetic.

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