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Today’s Take on 2000s Style: Ivy, Emo, and Athleisure

Some of the most recognizable menswear trends of all time have come from the 2000s, a decade not necessarily celebrated for its style (yet) though iconic in every sense of the word.

By: Harry RosenDate: 2024-10-07

What are your memories of style in the 2000s? Many perceive this decade as part of menswear’s grey era, one that struggled to settle on just one defining image and instead experimented with a few, vastly different trends.


The 2000s was a decade in style that will forever be synonymous with a few trends in particular; the invention of athleisure, the resurgence of ivy, and the heyday for emo. Within the universe of Harry Rosen, the decade was also a time of great transition.



Embrace Your Dark Side

male wearing black clothing with city in background

The 2000s saw the emergence of emo and scene subcultures, defined by a distinctive dark fashion aesthetic. This style was heavily influenced by the emotional music genres of the time (think Jimmy Eat World and Dashboard Confessional) and was characterized by skinny jeans, band T-shirts, and studded belts.


Today’s Take


While many will revert to basic black today, we’re inspired by new looks from DRKSHDW that are giving us revamped emo vibes. This label offers edgy, minimalist designs and innovative fabric treatments, blending luxury with urban style. Start with a pair of cargo pants or skinny jeans in black or a dark wash. Pair them with a graphic T-shirt or a vintage-style tee. Express your individuality and deep connection to music by accessorizing accordingly.


Balmain Logo Embroidered Bomber

Balmain

Logo Embroidered Bomber

$1714.99$2450Save 30%
NEUW Band Organic Cotton T-Shirt

NEUW

Band Organic Cotton T-Shirt

$89
Patrick Assaraf Stretch-Pima Cotton T-Shirt

Patrick Assaraf

Stretch-Pima Cotton T-Shirt

$135
Purple Brand Distressed & Faded Jeans

Purple Brand

Distressed & Faded Jeans

$325
Represent Owner's Club T-Shirt

Represent

Owner's Club T-Shirt

$195
C.P. Company Military Tapered Pants

C.P. Company

Military Tapered Pants

$425
Officine Creative Anatomia 013 Distressed Leather Lace-Up Boots

Officine Creative

Anatomia 013 Distressed Leather Lace-Up Boots

$895
Rick Owens DRKSHDW Low Top Retro Sneaker

Rick Owens DRKSHDW

Low Top Retro Sneaker

$745

Everyday Ivy

male wearing Canali Kei sport jacket with city in background

Born out of Ivy League schools in the 1960s, prep experienced a significant revival in the 2000s thanks to brands like Ralph Lauren, which brought classic staples like polo shirts, chinos, and loafers back into mainstream fashion. This style is celebrated for its clean, polished look, pops of colour, and a focus on quality.


Today’s Take


A preppy Ivy League look is always in if that’s your style: start with a well-fitted polo shirt, paired with a pair of chinos in a neutral colour like beige, navy, or khaki. Complete the outfit with loafers for a classic preppy touch.


For cooler weather or a more polished appearance, add a sport jacket in a complementary shade, like the Kei jacket by Canali. Accessorize with a bag or briefcase, such as the woven briefcase from Officine Creative, because you never know where your day (or life!) will take you.


Canali Textured Geometric Silk Tie

Canali

Textured Geometric Silk Tie

$195
Canali Jersey Sport Shirt

Canali

Jersey Sport Shirt

$425
Canali Washable Pants

Canali

Washable Pants

$650
Polo Ralph Lauren Herringbone Wool-Blend Sport Jacket

Polo Ralph Lauren

Herringbone Wool-Blend Sport Jacket

$1028
Paige Danford Slim Fit Stretch-Cotton Chino Pants

Paige

Danford Slim Fit Stretch-Cotton Chino Pants

$235.99$315Save 25%
A.P.C. Oxford Button-Down Collar Sport Shirt

A.P.C.

Oxford Button-Down Collar Sport Shirt

$257.99$345Save 25%
Magnanni Línea Flex Collection Delrey Drop Tassel Loafers

Magnanni

Línea Flex Collection Delrey Drop Tassel Loafers

$550

All-Access Athleisure

male wearing athletic wear by Rhude with city in background

The 2000s witnessed the rise of athleisure, a trend that blurred the lines between gym attire and everyday wear, making it fashionable to don athletic gear outside of workouts. Spurred on by celebrities and athletes, athleisure reflected our cultural obsession with health-conscious lifestyles. In turn, hoodies , track pants, and sneakers have become wardrobe essentials.


Today’s Take


Start with a vibrant hoodie or a complete track suit from one of our designer brands, like Rhude from Los Angeles. Finish the look with one of our many stylish sneakers from New Balance. This versatile outfit can easily transition from running errands to casual outings, ensuring you stay comfortable and fashionable.


Rhude Cotton-Blend Quarter-Zip Track Jacket

Rhude

Cotton-Blend Quarter-Zip Track Jacket

$1094.99$1825Save 40%
New Balance 1906R Sneakers

New Balance

1906R Sneakers

$200
Rhude Cotton-Blend Track Pants

Rhude

Cotton-Blend Track Pants

$665.99$1110Save 40%
Represent Patron Of The Club Joggers

Represent

Patron Of The Club Joggers

$285
Salomon ACS + CSWP Sneakers

Salomon

ACS + CSWP Sneakers

$235
Represent Patron Of The Club Hooded Sweater

Represent

Patron Of The Club Hooded Sweater

$325
Canada Goose Huron Jersey Cotton Joggers

Canada Goose

Huron Jersey Cotton Joggers

$295
Canada Goose Stormont Merino Wool Half-Zip Sweater

Canada Goose

Stormont Merino Wool Half-Zip Sweater

$550

What Was Happening at Harry’s?


The transition into the 2000s was marked by Larry Rosen, Harry’s eldest son, succeeding his father as Chairman and CEO. For the first time ever, the family-run company was under the leadership of its second generation.


With more time on his hands, Harry made a return to store-level in his later years with the company, reinspiring the format and concept of trunk shows. Harry always had a special love for trunk shows since he initially introducing Italian labels such as Canali, Giorgio Armani, and Zegna to the Canadian market in decades past, which led him to reinvigorating that section of the business once again.


In 2005, Harry stepped down from all day-to-day operations, though retained roles as an Executive Chairman and as a trusted advisor.


A few years later in 2008, Larry Rosen made the astute decision to capitalize on the ever-present dot com wave and launch harryrosen.com, becoming one of the first luxury retailers to create an eCommerce marketplace. Today, harryrosen.com is a thriving and essential sector of Harry Rosen’s overall business.

TAGS:#Fashion,#Places,#Trends,#Harry Magazine,