“When you put together a good outfit and you step outside you just feel more confident in yourself.”
Ethan Martinez looked at the clothes hanging in his closet in seventh grade and thought it was time for a change.
The colorful T-shirts from his parents with graphics of kids characters didn’t seem appropriate for a soon-to-be high schooler. That’s when he started shopping for himself. Now, Ethan, 16, follows the trends and styles his own everyday “fits,” slang for a put-together look.
But during the school year, he prefers comfort over style as he walks the halls at Lincoln Park High School. There is one exception: the first day. For Ethan, looking sharp for that opening bell is key to starting off his junior year right.
“You can’t just go to your first day of school wearing pajamas,” Ethan says. “You ever hear the saying that first impressions are the best impressions?”
Ethan is one of the many Chicago Public Schools students who start piecing together their outfits weeks before reuniting with friends and teachers. Their individual styles offer a chance to showcase their personalities and, in some cases, introduce new versions of themselves to their classmates as they return from summer break. Classes begin Monday for most Chicago schools.
Ethan says he started thinking about what he wanted his first day outfit to look like back in the middle of the summer. He envisioned a simple but stylish pairing of cargo shorts — a trendy item — with a sweater and Air Jordan sneakers to match his top. Other brands that he likes include Under Armour, Calvin Klein, Nike and Levi’s.
He says he doesn’t adhere to a particular style but takes inspiration from musicians like rapper Lil Baby and Mexican artist Tito Double P.
Ethan says he feels like he can do anything when he’s wearing something snappy.
“When you put together a good outfit and you step outside, you just feel more confident in yourself,” Ethan says. “You ever walk by a clean window, and you just can’t stop staring at yourself? It’s kind of that feeling.”
“Just wear what you want to wear and don’t care about what other people are going to think about your outfit. Wear something that you feel good in.”
Sasha Levy, who is starting her freshman year at Whitney Young Magnet High School, also believes in the mood setting power of clothing. She dresses up when she wants to be in good spirits. When she thinks a day might be stressful, she prefers comfort over being chic.
But Sasha, like Ethan, thinks it’s important to show up with a good outfit on the first day.
She decided on a pastel yellow, pink and blue Hollister tube top and long jean shorts paired with a gray and white Adidas sneakers.
“I just want people to think I have good style,” Sasha says. “I just want [my outfit] to look cute, like a good first impression.”
Sasha likes to shop at Brandy Melville but also scours websites for anything that catches her eye. She’s noticed babydoll tops that flare out at the bottom are a popular item this year. Any getup she puts together is accented with gold jewelry, Sasha’s favorite.
Her style is influenced by the personalities she follows on TikTok and other social media platforms. If they’re wearing something that she likes, she says she thinks, “Oh, wow, I want to get that.”
But those items aren’t always grown-up approved. Sasha says her grandmother sometimes gives her grief over crop tops or tube tops.
“Because that’s a classic, like you’re showing too much skin,” Sasha says.
For Sasha, the trends, brands, styles or the opinion of others aren’t all that important in the end. The only place teens should be turning for fashion advice is in the mirror, she says.
“Just wear what you want to wear and don’t care about what other people are going to think about your outfit,” she says. “Wear something that you feel good in.”
“You can accessorize your uniform, you can decorate your little school bag, you can decorate everything. When you have a uniform you can create what you want to wear.”
Pharrah Harper, a freshman at the University of Chicago Charter School, also has experienced resistance to crop tops from the older crowds, as well as to the loose fitting cuts that are en vogue.
She thinks it’s good that parents pay attention, but they shouldn’t stifle a teen’s need to convey their individuality through what they wear.
“That’s how we, like, really like to express ourselves and want people to, like, understand us. So … just let us get a little short crop top once in a while, make us look cute,” she says, as long as it isn’t too short.
Showing off her personality through clothes takes a little more effort for Pharrah. She’s required to wear a uniform consisting of a shirt with the school logo and khaki pants or a skirt. But that doesn’t mean she can’t make it her own.
For her first day, Pharrah’s wearing high-top Converse sneakers and accessorizing with gold jewelry. Rather than feeling restricted, she thinks the uniform requirement is a chance for students to show off their imagination.
“You can accessorize your uniform, you can decorate your little school bag, you can decorate everything,” Pharrah says. “When you have a uniform, you can create what you want to wear.”
Pharrah also follows Tik Tok influencers to find inspiration for her own style. She isn’t loyal to a particular brand or store and prefers to shop around.
She doesn’t think students should put too much pressure on finding the perfect pieces to wear on the first day.
“Don’t stress, just [go with] whatever’s in your mind. And [if] you think you look cute in it … just go with it.”
Emmanuel Camarillo covers K-12 education for the Sun-Times. Araceli Gómez-Aldana is a WBEZ reporter and host.