Growing up, there are few days of the year with greater expectations foisted upon them than the first day of school. And so the first day of school outfit is particularly crucial—it’s that initial swing everybody takes, simultaneously, at letting everyone else know what they’re all about now. Maybe it’s an introduction. Maybe it’s a re-introduction. Maybe it’s a reinvention! Either way, it always seems to feel very important. Photographer Olivia Wein, a New York City-based high school senior, invited some friends to Man Repeller HQ last week to take photos of their sacred first-day ensembles. Here, they share the thought process behind them.
Noah Schaub, 17 (Senior)
My look: I used to conform to societal masculine norms—sweatpants, a logo t-shirt. It was so binary and boring. In the past year, I’ve finally come into myself. It took a lot of internal work and reflective writing, but we’re here. I want to show other people that they can wear whatever they want. I love people who wear freaky shit.
How I got it: I saw this shirt at a thrift store last weekend and I thought, Oh my God, this is perfect. My dad gave me these jeans three days ago because I was like, “I need jeans.” I wanted to paint on them but he said I can’t. My friend Sidney did my makeup today. I wish I was like James Charles or Jeffree Star makeup-wise, but I’ve got to practice.
My inspiration: I watch a lot of thrifting haul videos. There’s a YouTuber named Internet Girl and she makes bundles of clothing and sells them to people. The bundles usually have a theme, it’s very interesting. I’ve gained more of a vocabulary about certain types of clothing from watching videos about thrifting—that’s how I know my look is more Y2K.
Evangelia, 17 (Senior)
My look: My outfit is very school-girl influenced. I wanted to wear something preppy, but I wanted it to have a little flair, so I went with the glittery makeup look, which is kind of Euphoria-inspired. I only really have two pairs of shoes, but I think these dress shoes go really nicely with long socks and I wanted to wear something flirty and fun for the first day—show off a little leg right off the bat.
How I got it: Both the top and the skirt are from a thrift shop in New Jersey called Bo’s Attic. They cost me about a dollar and 30 cents each. I’m close with the owner. I actually bought the shirt because I went to a student leadership program this summer, so this was going to be one of my business ‘fits. The shoes I got in Greece last summer. They look like Dr. Martens but they’re not. They hold up just as well and cost me about 15 euros. This necklace is from Dolls Kill which is kind of fast-fashion. It was only 12 bucks but I feel like it’s a good statement piece. My earrings are from Rainbow, I think. The clips are just from beauty supply stores.
I use Depop, Pinterest, We Heart It, and Instagram bookmarks to keep track of inspiration. That’s something I’m very passionate about. I had a paid internship at a graphic design company this summer and they basically had me explain to them what was cool and hip for Generation Z. I would just make huge mood boards based on all of the things I had saved.
What I hope happens this year: This year, I’d like to pursue my creative endeavors a lot more. I’ve been trying to build my writing and drawing skills. I’ve already started working on bigger projects, but I would love to actually establish myself as an artist in the New York underground scene. Personally, I’m just trying to find stability in being alone more. I think the most important thing you can do for yourself is establish a strong sense of identity and be comfortable with your social location.
Shandra, 17 (Senior)
My look: This summer was a hot girl summer so I’ve been partying a lot and hanging out with my friends. I’ve never shopped at Rainbow, but everybody says it’s great if you want something cheap and you’re just going to wear it to a party or something. So I was like, “It’s hot girl summer. That’s the move.” I went there with my best friend—well, ex-best friend—and she was like, “This would look so good on you.” I was like, “Really? I don’t know. I’ll think about it.” A week later I went there again with two other friends and they were like, “Shandra! You have to get this outfit.” It’s not really something I would normally wear because I’m more into baggy urban street style. I just thought it was interesting that all my friends had the same view of me.
My makeup: A lot of people know me for drawing face tattoos on myself with makeup—for me, makeup is expression—but since this outfit was so different, I wanted a very sleek, clean look. I’m actually bald with green hair under this wig, but I knew I wanted a nice slick, low bun with some nice sassy vibes. I did the lip liner, and I was like, that’ll be bold, like, I’m hot, but I’m still cute. I love mink lashes. I’m so dramatic in everything I do, so I always have really long, dramatic lashes.
My take on first-day hype: I feel like stressing over first-day outfits is more middle school or freshman year because you want to look cute for boys. Me? I’m like, I don’t care what you think about me. I’m cute regardless, baby. This year, all I’m thinking about is college and the fact that I’m about to be out. Bye!
Maya, 16 (Junior)
Can you tell me about your look?
The boots I’m wearing are actually my favorites. I bought them off my friend because I was always borrowing them. They go up really high. I love them so much. The pants are a recent buy. I bought them specifically with the idea of, How can I show up back to school with my same style, but also kind of show off? I love them so much. I bought them online and it’s one of the first times an online purchase actually fit my proportions pretty well. The belt is my dad’s. The shirt was given to me by my grandma. I get all my clothes from her. The neon green glows under a black light. It’s super weird and random. I adore it so much.
What do you want your first day outfit to say?
I know I’m going to have the chance to wear this for the rest of the year, but that first day just has to be the reminder that… can I swear?
….I’m still that bitch. It’s like, I’m still here. I didn’t change over the summer. Or maybe I did and this is the representation of it.
Do you normally plan your outfits in advance?
Only sometimes. I have a very serious streak of getting to school late, mostly for that reason. I procrastinate a lot, so I don’t plan my outfits out very often, unless it’s something like the first day of school. I bought these pants specifically for that. And I originally had another pair of shoes that I also bought for back to school, but as much as I love them, I scrapped them because I’ve got to keep it fresh.
What do you hope happens this year?
I was actually thinking about this a little while ago: Fashion is something I want to go a little deeper into. I feel like my sense of style didn’t really develop until last year. The year before that, whatever was big, I liked. But I’ve met a completely different group of friends that I’ve connected with way more. My friend and I started a band, so we see way more of that artistic scene. We play a lot of punk rock, specifically fem-oriented punk rock. We’re inspired by Siouxsie and the Banshees and Hole. I think from there, I was able to realize, Oh, I don’t need to do everything BuzzFeed tells me to do.
Zarvon, 16 (Senior)
Can you tell me about how your outfit came together?
This is going to be my last first day of school, so I wanted to do something a little bit more flashy. I just got these new pants on Grailed—they’re Nike x AMBUSH. Lately, I’ve just been trying to dress as weirdly as possible while keeping it all black, kind of dressing like a ninja. These Dior sneakers are my favorite shoes and then I just threw on this regular Supreme T-shirt. I try to not put too much effort into my outfits. Also, one thing I don’t like is matching. I feel like matching is too easy.
Have you had most of these things for a while or are they all new?
I really just got into fashion, like, sophomore year of high school. I remember the moment I decided I had to dress good: I put on these Brooks Brothers green pants with a baby blue polo shirt and when I came into school everyone completely roasted me. They were like, “You got dressed in the dark! What’s wrong with your outfit? Do you know how to match colors or anything?!” So then I went shopping with some of my friends—one of my friends, Axel, really helped me out. I used to shop at H&M and Zara a lot, and I used to look up to rappers to copy outfits, like Travis Scott or A$AP Rocky. But the more I got into fashion, I just started to develop my own sense of style.
How big of a deal is a first day of school outfit to you usually?
I don’t really care about first day of school outfits. In the fourth grade or something, I had a Winnie the Pooh shirt that I thought was really fresh and I really wanted to wear that. But now I feel like everything is all about Instagram, that’s where people see your outfits. Honestly, I feel like you shouldn’t wear your best outfit on the first day of school because you’re setting the bar too high. You should have some chill.
Jian, 17 (Senior)
How’d you put your outfit together?
I wanted to do a tonal look, so I chose red and then I mixed textures—cotton, silk, the elastic on the belt. Because it was dressy, I put on Converse to make it a little more plain or casual.
Sounds like you have an advanced approach. How into fashion are you?
It’s a pretty big part of my life. My mom was always into fashion, so it was introduced to my brother and I early on. If I don’t like my outfit it’ll literally ruin my day. It sucks that it has that control, but it’s a fact.
Red is a bold color to go with for the first day.
I know. Red is my favorite color because in Chinese culture it’s considered lucky. I honestly like to wear black all the time, but I feel like for the first day of school you should try something different to make an impression.
How does makeup factor in?
I don’t wear a full face. I have admiration for people who can do that, especially for school. I know of people who wake up an hour early to do their makeup and there’s always a girl in the bathroom doing her makeup because her parents don’t let her leave the house like that. Good for them. But I don’t wear any foundation, concealer, bronzer, or anything. I’ve been becoming more interested, but honestly, I like the way my face looks when it’s more chill.
What do you want to study in college? Do you know?
I’ve been interested in international relations for a while because I’m so fascinated by different cultures and languages and food and stuff like that. But recently I’ve become more interested in environmental [issues]. Everyone I say that to is like, “We need it.” I genuinely want to help fix the world.
Indigo, 15 (Junior)
My look: Putting together a first-day of school outfit is fun. I would like to say that I don’t care about it, but I do. There’s no stress though, I’m just doing it for me. I got this skirt in the winter so I haven’t been able to wear it enough yet. It’s darling in my opinion. And so is the shirt: cute, innocent enough, not too flashy, it just says, “hey.” The shoes I chose are my tried-and-trues. I got them at a thrift store for $5. They’re dirty, but that’s okay. All of my clothes are thrifted. I think it’s a talent. You have to find your own stuff and make something out of it.
My inspiration: I follow a lot of those runway archive pages on Instagram. I also get inspired by what I find in thrift stores. Sometimes one thing can shape an outfit. Also, David Bowie. It’s not like I want to dress like him, but I think he’s so cool for being him. My mom showed me a parody of the “Space Oddity” video—and I was like, Whoa, I like this song, so I watched the original.
What I hope happens this year: I’m moving back to Florida. I used to live there and then in 9th grade I moved to New York because my dad lives here. But I’m moving back down, and it’s going to be awesome because I’m going to get a car. I’m really excited. I’m doing online school which gives me my own timeline. I’ll probably still get dressed for online school—a cute top and some sweatpants. I have these Juicy Couture tracksuit bottoms that I always pair with a cute shirt. I’m like, This is stylish. It’s Juicy.
Juliet, 14 (Sophomore)
The look: It depends on the day, but I like my clothes to be either extremely bright and glittery or dark and fitted. Usually when I’m wearing bright clothes, I add gems. I feel like it highlights my face and adds a little sparkle. I got my shirt off Depop, which I think is a really cool site. I think it’s important in this time, because you’re not wasting anything. People are sharing things that they’ve loved and passing them on to the next person. I’m really into flare jeans, like, 2000s low-waisted. I know people hate on low-waisted a lot, but they’re coming back.
What I want it to say: My outfit represents a more positive outlook on school. Last year, starting at a school I didn’t really want to go to was a difficult experience. My first first-day look was a little eerie, in a sense. I didn’t really want to be there. I didn’t want people to form an opinion on me because I didn’t want to be there for that long. But now I’ve started to like it better—I’ve gotten more into art—so my second-year first-day look is more positive.
My inspiration: Honestly, I get inspiration from a lot of people who go to my school. Everyone has really unique style. I don’t stick to a certain look. One month it’ll be more of a Y2K, 2000s thing and another day it’ll be more like a 90s, grungy style. My dad is a glass blower, so he grew up in an artsy scene in college. I see all his pictures from there and sometimes I get inspiration from that. He’s always telling me little things—like tie-dye and baggy jeans—and then when they come back into style he’s like, “I told you so.”
Ellison, 17 (Senior)
Tell me about your first-day look.
For the first day of school, I wanted something I’m comfortable in. School always brings up such bad anxiety issues—I mean, I feel like it does for everybody—so I wanted to make sure I’m wearing something I know I feel good and look good in. This shirt came to mind. It’s by Our Legacy. I got these camo pants on Depop for, like, $30. I saw the shoes in Opening Ceremony and I really considered getting them for a minute! Then I was like, Ellison, what are you thinking? You can’t do this! So I went onto Grailed and found them in perfect condition.
Love when that happens.
Such a good feeling.
What’s the story with your tiny Jacquemus bag?
This was my birthday present from my mom because Simon Porte Jacquemus is one of my favorite designers. His lavender thing that he just did—it was so good. I like that this was the invite to the fashion show. When he put it on sale, I was like, “Oh my God, this is it. This is what I want for my birthday.” I describe it more as a necklace than an actual accessory because you can’t really fit anything of substance in there. I can fit like one AirPod and that’s it.
Is your mom into fashion too?
Well, I have two moms. One of them is a photo producer and before that she was a documentarian. My other mom is a psychiatric nurse practitioner psychopharmacologist and she helps mainly teens and children with mental illnesses. So I don’t really know entirely where I got the fashion thing from, but I’ve got it and I have it really bad.
What do you want your first-day look to say?
I want it to say, “Yes, I’m tired, but I’m still going to be, like, a style icon all year and you can bet on that.” But I also don’t want to be too much of a bitch, because sometimes with the glasses I definitely give off that vibe.
Isabel, 17 (Senior)
How’d you put your outfit together?
I’m really into color coordination. I have this statement necklace and it makes me think of cotton candy, so I always like to do a blue and pink look with it. My friend gave me this blue dress and then I have all these butterfly clips from Amazon. I bought 100 and there are about 50 left. I feel like they make me look a little magical so I put them all throughout my hair. I always like to do my edges, so I did a hairstyle where I could do my edges while having my hair out. Then I put on the pink eyeshadow.
Can you tell me a little more about your makeup?
These freckles are fake. I used my friend’s eyebrow stuff, and I just dotted them on. I like doing different patterns and stuff, so I can have variation to the freckles. Today I thought it would just be a cute little moment. I’ve been into makeup for the past year, and I try as hard as I can to color code my eyeshadow to my outfit every day, if possible. Sometimes I like to do a rainbow during the week and if I can’t do a certain color, I get really upset, because I want it all to be in order.
How far in advance did you plan your outfit?
Two weeks. It’s really fun for me, because I like piecing everything together and making everything perfect. The first day of school also isn’t more important than the rest of the days. I have more time to prepare for the first day, but then I think of my second day outfit, then the third day. Later on, I just think of it the night before.
Nico, 15 (Junior)
My look: I wasn’t sure what to wear. These are all clothes I thrifted this summer. I knew I’d want to wear something no one had seen me wear before. The look is pretty traditional, but I felt like the shorter skirt and shoes made it my own. The shoes belonged to my mom, and she gave them to me as something special for my junior year, so I really cherish them because they’d been with her for so long.
My inspiration: I have a bunch of old fashion magazines stacked up at my house and I look through a lot of those. Seeing clothes from past eras has always interested me. This year, I got really into corsets and corset belts and it just happened to be what was in fashion.
What I hope happens this year: Last year was a really rough year for me. I have epilepsy, so I struggle with my health a lot. This year, I hope I can just focus on my school work. Since I’m going into junior year, I get to be in the first public performance at my school. (We only get to perform in the plays as juniors and seniors.) That’s a big thing that I’m really looking forward to. I just hope that I don’t stress myself out too much—I already have a part-time job and I want to be able to see my friends and stay connected to everyone.
Jack, 14 (Freshman)
How did you go about choosing your outfit?
I kinda wanted something that might appeal to a lot of different people because I’m not really sure what kind of people I’ll end up being friends with this year. I have my dad’s old Beatles shirt on that has some holes in it and paint on it and stuff. It’s really soft and comfortable. The pants I’ve had for a while so they’re worn down a little bit, a little bit more comfortable, and the shoes are hand-me-downs from my step-brother.
Do you borrow t-shirts from your dad a lot?
Yeah, he has a lot of really old, soft t-shirts and they’re good pajamas and stuff. I wear them a lot.
So, if you’re interested in what someone is wearing, does that make it easier to strike up a conversation?
Yeah. That’s why me and [sister and story photographer] Olivia both thought the band t-shirt would be cool because I’m really into music and stuff. If I see someone with a t-shirt from a band or a show that I know, that’s a way for me to relate to someone I don’t really know that well.
I forgot to ask about your necklace! What’s the deal with it?
The necklace is something I drew and my friend made for me. It’s a wolf head carved out of bone and blue pietersite, which is supposed to be like the eye of the storm—kind of focused and relaxed.
Photos by Olivia Wein. Produced by Sabrina Santiago.