As we attempt to prepare ourselves and our wardrobes for the impending Fashion Week (and autumn to follow), it feels like planning outfits for the first day of school. Long before the days of Insta-selfies and street style, clothes selected for the much-anticipated return to the hallways carried serious weight, sending coded messages about our vacations (see: concert tees, friendship bracelets, tan lines) and setting the tone for the school year ahead. Questlove captured it best for us earlier this summer, at Madonna’s party at Harlow: “You know, the night before the first day of school, that outfit in your closet you can’t wait to rock?” he remembered. “Seventh grade. ‘Everybody’ was on. And my outfit kept staring at me. I was staring at my outfit all night, just imagining I was gonna rock people in the morning when they saw my outfit.” Read on to find out what Questlove wore to rock his classmates, along with Courtney Love, Jenna Lyons, Zac Posen, and several other designer’s favorite back-to-school looks. Then tell us about yours in the comments.
"Seventh grade. Back in ’83, beat boys were rocking these button-up pants, like Starter pants for NBA players when they rip their pants off. But for some reason it was stylish. It was like, maroon bell bottom-y [pants] that you snap up on the sides, and a pair of shell-top Adidas that my mom would not allow me to wear in August. She got them in July and I wasn’t allowed to touch them. [The first day of school] would have been the first time I was allowed to rock ’em. That and a “Hip Hop You Don’t Stop” graffiti T-shirt. Yeah. I was a beat boy back then."
"It would be about third grade. My parents were hippies. I had to go to this Montessori in a poncho – a poncho – and saddle shoes. And we were on a brewer’s-yeast fast, so my lunch was a brewer’s-yeast thing to drink. Me and my sisters had matching ponchos that my mother had made out of patches. Yeah. But my sister got to wear the Birkenstocks. I had to wear the saddle shoes. Really nasty. And by the way, I was so happy to be sent to boarding school in England after that, you have no idea. I got kicked out of that Montessori pretty quickly."
"My favorite first-day-of-school outfit ever: I had purple denim jeans that came almost up to my neck and a tiny little purple crop top with a giant Raggedy Ann and Andy belt, with a Raggedy Ann face virtually the size of a bull head and white go-go boots – plastic boots. I don’t know where I got them. I was probably 10 or 11. I remember it well."
"I dressed as Charlie Chaplin for my first day of high school: bowler hat, long coat (oversize), pinstriped pants in gray charcoal, patent-leather shoes, white tuxedo shirt. I probably had an umbrella, to take the place of a cane. That’s how I bizarrely chose to present myself. I met my best friends of life through that, in my first class."
"Oh, I’m sure it was just a hot mess. I grew up in Tucson, Arizona, rather in poverty. So my school shopping was like Salvation Army and Goodwill. I could try to look like the other girls, wearing Guess and Esprit and Keds at that time. So there was one year, this is a true story, I got white jeans. I drew on the Guess triangle. I got cheap canvas “Keds” and drew on the blue — you know how there was just the blue square on the back? I think I faked it with the Guess jeans and the Keds. Kind of sad, but kind of cute — kind of resourceful. Yeah, because from far away it was like: Yeah, those are Guess; those are Keds."
"I grew up in Saddle River, New Jersey, so I would say it’s quite conservative and preppy. I was 13 and I had started sneaking to New York City on a bus when I was like 12. There used to be a store called Antique Boutique on lower Broadway, back in the day, and there were these UFO parachute pants — huge balloon pants, with a drawstring on the bottom. I was fully into New Wave: [I] had the long hair, shaved all on the side and the back, and the long bangs. I came back dressed in head-to-toe black, with like drawstring pants that looked a bit like ninja pants, I guess, to other people. It was pretty controversial, I have to say, when everyone else was wearing Ralph Lauren and Tommy Hilfiger."
"I was obsessed with Hawaiian shirts and I got one. I knew that it was fall, but still, I didn’t care. I got this Hawaiian shirt with this woman on the back that was doing the little Hawaiian hula dance. It was crazy. I paired it with jean shorts and high-tops. This was in sixth grade. I don’t think that I got any good reactions, but for me, I thought it was pretty awesome."
"I remember my first dress that my mom bought me that I really loved, that I wore to school. It was Diane Von Furstenberg. I was probably like 12. I was very tall. It was pink with a white collar, a little white piping, a little pink belt. It was adorable. I’m like, 'Oh my god! Diane Von Furstenberg!' I felt like royalty."
"I don’t remember mine, but I would always style my brother, so my favorite moment for him, I styled him as Huey Lewis and the News: So, the red blazer, I put him in periwinkle Converse, and he had to listen to me."
"I used to go to this boarding school where we rode, and I had these brick [red] britches that no one had at that time and I wore them all the time. My mother had sent me off to this school called Foxcroft. I was not a happy camper there, but I had these britches and I wore them all the time. It really made all the girls crazy. They were all trying to get them and no one could them. Then they were very, very popular."
Mark Badgley and James Mischka
Badgley: "I know mine. It was a burgundy, check, madras button-down short-sleeved shirt with khaki pants and matching burgundy cordovan Bass Weejun loafers. It was like third [grade]. I had a little bit to say in it." Mischka: "Mine was third grade also. I lived in Malibu and I wore yellow-and-purple tie-dyed bell bottoms and a T-shirt and a head full of love beads."
"I actually have a photo of it. I throwback Thursday-ed it. It’s a multi-striped jumpsuit and I was in like second grade. With a red blazer. We had to wear a blazer to school. It was an independent private school, so it was like, blazer, tie. My parents were crazy about prints and I still am to this day. I live for weird prints. I think it’s ingrained. It’s a lifelong thing — color and prints."
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