
Uly Pashkova / Wikimedia Commons (CC BY-SA 4.0)
Every generation swears their fashion is timeless. Every generation is wrong. These trends dominated runways, red carpets, and your Facebook photos — and now they live rent-free in your cringe memories. If you owned any of these, congratulations: you were fashionable. You were also wrong.
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In 2003, Paris Hilton, Ashton Kutcher, and every person who watched The Simple Life made mesh-backed trucker hats a $300 luxury item. Von Dutch hats originally cost gas station prices, then celebrity endorsement inflated them into a status symbol. The brand filed for bankruptcy by 2009. The hat that was supposed to signal effortless cool now signals "I peaked in 2004." Ed Hardy filled the same niche a year later with bedazzled tiger graphics, and somehow aged even worse.

The jean that required you to either never sit down or accept that the entire room would see your underwear. Britney Spears, Christina Aguilera, and the entire cast of Laguna Beach made hip-hugging denim the uniform of the early 2000s. Fashion houses tried to revive them in 2022 and Gen Z collectively said "absolutely not." The low-rise era weaponized body insecurity in ways we're still unpacking — turns out, fashion shouldn't require you to stop eating bread.

Nothing said "I have money and nowhere to be" like a $200 velour tracksuit with "JUICY" bedazzled across the backside. The brand hit $600 million in annual revenue by 2006, fueled entirely by celebrities photographed leaving Starbucks looking like they'd just rolled out of a luxury daybed. The parent company sold Juicy Couture for $195 million in 2013 — a 68% loss. The tracksuits live on in Y2K nostalgia TikToks and thrift store racks, which is exactly where they belong.

Each leg was 23 inches wide at the hem — wide enough to smuggle a small child. JNCO jeans were the uniform of the late-90s rave/mall-goth/nu-metal crossover, and wearing them required dragging denim through every puddle you encountered. The brand sold $186 million worth of comically oversized pants in 1998. They attempted a comeback in 2015. It lasted two years. Some things should stay in the decade that created them, and 50-inch leg openings are definitely one of those things.

Before Post Malone collabs and Balenciaga platform versions, Crocs were just foam clogs that your dad wore to mow the lawn. Mario Batali made them his signature chef shoe. George W. Bush wore them with socks to the White House. TIME Magazine put them on the "50 Worst Inventions" list in 2010. Then irony culture, Jibbitz charms, and celebrity collaborations turned them into a $3.6 billion revenue brand by 2023. The original era of earnestly wearing Crocs to dinner, however, remains indefensible.

There's slim-fit, and then there's the 2008-2015 era where jeans were so tight they cut off circulation to your feet. Pete Wentz, Russell Brand, and every Brooklyn barista made spray-on denim a personality trait. An Australian woman was hospitalized in 2015 after her skinny jeans caused compartment syndrome — her calves swelled so badly she couldn't walk. Gen Z officially declared skinny jeans dead in 2021 via a viral TikTok, and wide-leg pants reclaimed the throne. The pendulum always swings.

Diane von Furstenberg sent models down her Spring 2013 runway wearing Google Glass. Vogue shot a 12-page spread. The tech industry genuinely believed face-mounted computers were the next fashion accessory. Instead, wearers were nicknamed "Glassholes" and banned from bars across San Francisco. The $1,500 headset made every wearer look like a Terminator cosplayer who got lost at brunch. DVF's runway moment is now the definitive example of Silicon Valley confusing "new" with "desirable."

Australian sheepskin boots designed for surfers to warm up after dawn patrol somehow became a fashion staple when Oprah put them on her "Favorite Things" list in 2000. By 2004, you couldn't walk through a college campus without seeing Uggs paired with a North Face fleece and leggings — the unofficial sorority uniform. Deckers Brands sold $1.6 billion worth of Uggs at peak. The boots are genuinely warm and comfortable; wearing them to a nightclub with a miniskirt in 40-degree weather was the crime.

Between 2013 and 2016, every guy who'd grown his hair past his ears twisted it into a top-knot and called it a personality. Jared Leto, Harry Styles, and Gareth Bale made it mainstream. Barbers reported a 500% increase in "man bun consultations." The style required months of awkward growing-out phases and produced an entire cottage industry of YouTube tutorials. By 2017, the same men were getting undercuts. The man bun's legacy is primarily photographic evidence that proves we all make choices we regret.

MC Hammer made them famous in 1990, and for some reason, Justin Bieber and the entire H&M design team decided to bring them back around 2012. Drop-crotch pants create the silhouette of someone who has given up on both gravity and dignity simultaneously. Designers called them "relaxed" and "bohemian." Everyone else called them "the pants that look like you're wearing a full diaper." Paul Poiret introduced the original harem pant in 1911; he would be horrified to see what the 2010s did with his concept.
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In 2003, Paris Hilton, Ashton Kutcher, and every person who watched The Simple Life made mesh-backed trucker hats a $300 luxury item. Von Dutch hats originally cost gas station prices, then celebrity endorsement inflated them into a status symbol. The brand filed for bankruptcy by 2009. The hat that was supposed to signal effortless cool now signals "I peaked in 2004." Ed Hardy filled the same niche a year later with bedazzled tiger graphics, and somehow aged even worse.

The jean that required you to either never sit down or accept that the entire room would see your underwear. Britney Spears, Christina Aguilera, and the entire cast of Laguna Beach made hip-hugging denim the uniform of the early 2000s. Fashion houses tried to revive them in 2022 and Gen Z collectively said "absolutely not." The low-rise era weaponized body insecurity in ways we're still unpacking — turns out, fashion shouldn't require you to stop eating bread.

Nothing said "I have money and nowhere to be" like a $200 velour tracksuit with "JUICY" bedazzled across the backside. The brand hit $600 million in annual revenue by 2006, fueled entirely by celebrities photographed leaving Starbucks looking like they'd just rolled out of a luxury daybed. The parent company sold Juicy Couture for $195 million in 2013 — a 68% loss. The tracksuits live on in Y2K nostalgia TikToks and thrift store racks, which is exactly where they belong.

Each leg was 23 inches wide at the hem — wide enough to smuggle a small child. JNCO jeans were the uniform of the late-90s rave/mall-goth/nu-metal crossover, and wearing them required dragging denim through every puddle you encountered. The brand sold $186 million worth of comically oversized pants in 1998. They attempted a comeback in 2015. It lasted two years. Some things should stay in the decade that created them, and 50-inch leg openings are definitely one of those things.

Before Post Malone collabs and Balenciaga platform versions, Crocs were just foam clogs that your dad wore to mow the lawn. Mario Batali made them his signature chef shoe. George W. Bush wore them with socks to the White House. TIME Magazine put them on the "50 Worst Inventions" list in 2010. Then irony culture, Jibbitz charms, and celebrity collaborations turned them into a $3.6 billion revenue brand by 2023. The original era of earnestly wearing Crocs to dinner, however, remains indefensible.

There's slim-fit, and then there's the 2008-2015 era where jeans were so tight they cut off circulation to your feet. Pete Wentz, Russell Brand, and every Brooklyn barista made spray-on denim a personality trait. An Australian woman was hospitalized in 2015 after her skinny jeans caused compartment syndrome — her calves swelled so badly she couldn't walk. Gen Z officially declared skinny jeans dead in 2021 via a viral TikTok, and wide-leg pants reclaimed the throne. The pendulum always swings.

Diane von Furstenberg sent models down her Spring 2013 runway wearing Google Glass. Vogue shot a 12-page spread. The tech industry genuinely believed face-mounted computers were the next fashion accessory. Instead, wearers were nicknamed "Glassholes" and banned from bars across San Francisco. The $1,500 headset made every wearer look like a Terminator cosplayer who got lost at brunch. DVF's runway moment is now the definitive example of Silicon Valley confusing "new" with "desirable."

Australian sheepskin boots designed for surfers to warm up after dawn patrol somehow became a fashion staple when Oprah put them on her "Favorite Things" list in 2000. By 2004, you couldn't walk through a college campus without seeing Uggs paired with a North Face fleece and leggings — the unofficial sorority uniform. Deckers Brands sold $1.6 billion worth of Uggs at peak. The boots are genuinely warm and comfortable; wearing them to a nightclub with a miniskirt in 40-degree weather was the crime.

Between 2013 and 2016, every guy who'd grown his hair past his ears twisted it into a top-knot and called it a personality. Jared Leto, Harry Styles, and Gareth Bale made it mainstream. Barbers reported a 500% increase in "man bun consultations." The style required months of awkward growing-out phases and produced an entire cottage industry of YouTube tutorials. By 2017, the same men were getting undercuts. The man bun's legacy is primarily photographic evidence that proves we all make choices we regret.

MC Hammer made them famous in 1990, and for some reason, Justin Bieber and the entire H&M design team decided to bring them back around 2012. Drop-crotch pants create the silhouette of someone who has given up on both gravity and dignity simultaneously. Designers called them "relaxed" and "bohemian." Everyone else called them "the pants that look like you're wearing a full diaper." Paul Poiret introduced the original harem pant in 1911; he would be horrified to see what the 2010s did with his concept.