The Hundreds Pays Homage to Y2K Streetwear in Winter 2023 Collection

Featuring a limited-edition Anniversary Jacket by Jay 305, as well as collaborations with Amber Vittoria and Heathcliff.

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The Hundreds draws heavy inspiration from OG streetwear styles and silhouettes across all of its collections, but for the legacy Los Angeles label’s 20th anniversary, it’s really tapping into the early days of the city’s streetwear scene. Throughout the year, The Hundreds has dropped off retro-rooted capsules in honor of its 20-year milestone – including a vintage Summer 2023 capsule and a nostalgic Fall 2023 offering  – exploring the years of cultural history behind the brand. For its latest commemorative 20th anniversary delivery, the Winter 2023 Collection, The Hundreds is serving up a slew of sportswear and workwear-inspired pieces, dripped in vibrant colorways.

A run of clean jerseys and heavyweight flannels dominate the offering, seeing LA motifs and imagery infused throughout. Patterned tees pair perfectly with minimalistic, monochrome hoodies, whereas other tops and jackets take heavily branded stances, emblazoned with Adam Bombs and other captivating graphics and slogans.

Though the Anniversary Jacket is the collection’s statement piece. Enlisting the likes of West Coast artist Jay 305, the letterman-inspired jacket combines wool and leather across the body, and retails for $449 USD. Check it out in the gallery below.

The collection also taps two other collaborators to contribute: multidisciplinary artist Amber Vittoria and cartoonist George Gately’s Heathcliff cartoon character. Vittoria, now on her second collab with The Hundreds, created the graphic “Folder Bar T-Shirt” and Heathcliff is stamped across the forefront of graphics as well. “First introduced in 1973 by cartoonist George Gately, Heathcliff has captured the hearts of fans across generations with his mischievous personality portrayed through a series of comic strips,” The Hundreds notes in a caption. “In continuation of our 20th-anniversary celebration, this year’s Winter 2023 Collections features a couple of collaborations within the mainline collection.”

 

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The Hundreds Winter 2023 collection is available to shop now on The Hundreds’ official online store.

In other streetwear news, PLEASURES and PUMA hit the desert for the duo’s second collaborative venture.

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Elaina Bernstein
Elaina Bernstein Editor

Elaina Lauren Bernstein is a New York-based writer and editor, overseeing Hypebeast's music vertical, Hypetrak. She handles both editorial and social coverage for Hypetrak, and served as the Deputy Editor for Summer 2025's Hypetrak Magazine — the first in 10 years. With a particular affinity for underground hip hop, she has racked up a wide range of interviews and cover stories, spanning A$AP Rocky, Larry June, Shaboozey, Leon Thomas, Rihanna, Brent Faiyaz, Jean Dawson, and Miguel, and has covered major music tentpole events including the Grammys and Coachella. The intersection of fashion and music guides her coverage as well.

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