1990s

In the late 90s, as pictured in hundreds of beloved movies and TV shows, students could be seen around high school campuses with crop tops and platform shoes or baggy tops and even baggier pants.

Style was heavily influenced by music genres such as hip-hop and grunge, with teenage boys expressing their tastes with oversized jeans and streetwear trends.

On the other side of the rebellious and youthful spirit of fashion, there was influence from celebrity models such as Cindy Crawford and Naomi Campbell. There was an established norm in fashion at the time, with clear trends and styles that most people would follow.

Dressing out of the ordinary and challenging the status quo was Woodbridge High assistant principal Christine Haley, expressing her feelings about music and art through her fashion choices.

“I was super punk rock and wore a lot of crazy colors,” said Haley. 

This was rare for the time, as Haley described there being only around three students in her school with similar styles.

As part of the norm, fashion was often attached to gender, with a distinction between more “masculine” or more “feminine” clothing.

However, as teens today increasingly borrow from the oversized styles of the 90s, Haley acknowledges that some aspects have changed—for the better.

“There’s always been trends in clothing that are either really feminine or really masculine. And today, the lines are blurred,” said Haley, admiring the shift away from such clear and separated lines of societal expectations for certain groups of people’s clothing.

In addition, there is no longer such uniformity, with significant diversity in accepted and normalized styles across high schools, including Woodbridge High. Students are free to express their own styles and personalities through their fashion, in much greater ratios than in Haley’s high school experience.

Accurate to the perceptions of many students today, fashion in the 2000s was characterized by bold colors, jerseys, and low-rise and baggy jeans.

English 1 teacher Megan Larson shared a firsthand account of high school fashion during the time.

Streetwear styles of the 90s stayed around, while influences from movies, magazines, and celebrities such as Britney Spears and Justin Timberlake gave the decade its own unique flair.

“This is also when thrifting was getting really popular, so I feel like everyone was just thrifting and that was influencing the style a lot,” said Larson. 

This reflects another resurfacing trend where teenagers can be seen wearing and seeking secondhand clothing from places like Goodwill.

As colder seasons came around, fashion trends could be seen changing as well. Teens dressing for winter in the 2000s enjoyed stylish boots, Mary Janesand loafers, as recounted by Larson.

Larson’s fashion today—along with that of many other students—still reflects the common style and trends from when she was a high schooler, though closer outside of school than while at work.

The styles of the 2000s have returned in full wave, quickly gaining popularity in the early 2020s, with social media users coining a new meaning for the term “Y2K.”

Associated with bright colors and pop stars, the decade quickly became a known and loved aesthetic of the new generation. Despite being relatively recent, the era was romanticized for its old-school atmosphere and presence in so many iconic TV shows and movies.

From 90s streetwear and baggy clothes, to 2000s shoes with layered laced tank tops, the fashion of the 2020s confidently reflects admiration of decades past.

What most positively sets the present-day high school fashion scene apart from previous years of trends is the freedom for self-expression and self-confidence. Students no longer feel the need to perform and look a certain way for others. Many are choosing to wear whatever they feel most comfortable or expressive in.

“When I was in school, people were still comfortable, but it definitely wasn’t as much like sweatpants, sweatsuits,” said Larson.

Despite heavy inspiration from past decades, the boldness of choosing comfort in 2020s fashion is a statement of dismissal of societal standards.

“It’s like, ‘I want to feel comfortable and this makes me feel good about my body and it maybe doesn’t fit like a traditional stereotype of what’s feminine, whether it’s tight or shows off certain parts of your body,’” said Haley, mimicking what she feels she sees in students’ fashion choices today.

Drawing from past years’ trends popularizing thrifting, many high school students now continue to enjoy buying secondhand, even leading to the creation of new apps such as Depop or Poshmark designed specifically for teens to post and purchase used clothing.

But with the decline of physical media such as magazines and the decrease in popularity of many high school-themed movies and TV shows, what influences how teens today dress?

The most obvious factor is social media.

Students point to influencers on social platforms, namely TikTok and Instagram, as the major determiners of which trends and styles become popular in the 2020s, including those returning from past decades.

As one creator features a new style or brand of clothing, everyone can be seen wearing it within the week. Stores themselves try to lean into this trait of the newer generation, leading to collaborations with young influencers and further differing from past brand connections being almost entirely reserved for major celebrities such as movie stars, music artists or supermodels.

Though also spreading in popularity primarily through social media, young celebrities also continue to influence beauty standards, including what is or isn’t objectively “cool” to wear.

As fashion continues to adapt to changing societal pressures and values, seemingly recycling and rhyming with past trends, unlikely connections are built across generations of high school students.