Back-To-School Fashion Memories (And Tips!) From Industry Insiders
Photo: WWD/Robert Mitra1/16Betsey Johnson
Fashion Designer
What's your favorite back-to-school fashion memory?
Wearing my padded Maidenform bra, my yellow tweed right-below-the-knee skirt, my yellow angora dolman sleeve turtleneck, my ponytail, my no-makeup-whatsoever face, and my polished white sneakers with white ankle socks. Wasn't I cute?
What are your first day of school styling tips?
Go to school looking like you! Feel comfortable, confident, and happy. Try to figure out who you are or who you would like to be more like because you are what you wear. Time will tell who you really are.
Photo: WWD/Kyle Ericksen2/16Whitney Port
Fashion Designer, Whitney Eve
What's your favorite back-to-school fashion memory?
I remember being into this red, white, and blue theme. I don't know why after the Fourth of July I decided that's what I wanted to wear the first day back to school. I wore these jean shorts with the American glad patched onto it and then this little red baby tee with a hot pink heart on it. I crimped my hair and had this whole Americana vibe going on.
What are your first day of school styling tips?
Clothing for school should really just be comfortable. Sometimes I wish I had a uniform at school, because sometimes clothes are something that separates people. But I think you should stay comfortable. It might be some cute skinny jeans with a tee, or some cute Converse. Simpler is better for school.
Photo: WWD/Steve Eichner3/16Prabal Gurung
Fashion Designer
What's your favorite back-to-school fashion memory?
I grew up attending a British Catholic school, so it was a challenge at times to put a personal twist on my uniform. I definitely managed to do so in some unexpected ways, even if it boiled down to my shoelaces.
What are your first day of school styling tips?
Stand out with a bright print!
Photo courtesy of DANNIJO4/16Danielle and Jodie Snyder
Jewelry Designers, DANNIJO
What's your favorite back-to-school fashion memory?
Danielle: My sister and parents gave me a legendary Free People jacket with a golden brown fur color and sick vintage-looking greenish fabric on the bodice. It zipped up in the front and I felt like Penny Lane in it.
Jodie: My patent leather Mary Janes and matching patent leather backpack. In the Nineties, Danielle remembers me "really believing in the power of matching accessories".
What are your first day of school styling tips?
Danielle: Just go for it. You'll look back and remember how much fun you had with fashion, so don't sweat it too much. I remember dressing like Jodie sometimes. I was such a tomboy. I didn't really care about clothes so much, but looking at Jodie made me think I should, and that I was really missing out by not getting involved in the label game. I'd wear these little turtleneck spandex top situations that were so awful and so not me that when I'd be half way through second period, I'd wish I had a change of clothes. My point in sharing this is have your own style and don't let anyone influence you to the point of dressing like someone else.
Jodie: I'd plan my first day of school outfit a week in advance at a minimum. I was so excited about it that I could barely sleep the night before. I used to take trips to New York to shop because Jacksonville wasn't the most fashion forward. My best advice is to get excited and stay excited. The first day of school matters. Don't let anyone let you think differently.
Photo: Fairchild Archive5/16Chris Benz
Fashion Designer
What's your favorite back-to-school fashion memory?
I remember when I was going back to school in sixth grade and I got a CK Jeans logo T-shirt. It was so major. It had the little C with the big K — totally a Nineties moment! I remember just loving it and wearing it all the time.
What are your first day of school styling tips?
Don't load all of your new stuff in one day. You should really pace it out so that you can always feel like you're wearing something new, at least for the first few weeks.
Photo: WWD/Steve Eichner6/16Claude Morais and Brian Wolk
Fashion Designers, Ruffian
What's your favorite back-to-school fashion memory?
Claude: I would wear my corduroy pants and my first plaid shirt and my little nylon jacket lined in flannel with my fresh new school bag and shoes. I think corduroy was my favorite fabric when I was a kid — it still is!
Brian: My style was much more Duran Duran-inspired. I had my Cavaricci jeans and my white doctor-inspired jacket and a pin-striped shirt with a gray deep V-neck sweater.
What are your first day of school styling tips?
Brian: We're really into a lot of a tapestries and brocades, so I think that's really fun for right now. A lot of cute tapestry and brocade dresses, kind of neo-'80s. We're also looking at a lot of cute socks.
Claude: For me, it's to keep it easy and functional with a new shoe and new accessories. Start very clean with a new white button-down shirt. Keep it simple, and accessorize a lot.
Photo: WWD/Steve Eichner7/16Nicole Miller
Fashion Designer
What's your favorite back-to-school fashion memory?
One summer my sister spent the summer in France. When she came back, she brought me clothes from all sorts of different French stores. I loved going back to school wearing pieces no one had ever seen and you couldn't find anywhere!
What are your first day of school styling tips?
For fall, you don't have to buy an entire new wardrobe to be stylish. Transition a summer maxi dress into fall with a chunky sweater and boots. Also, don't be afraid to mix prints, and even consider pairing pieces that clash and contrast; they can actually balance each other if you stick with the same colors. I love mixing masculine pieces matched with feminine ones. Try a military jacket with a floral dress. Jewelry always adds the finishing touch to any look. I love to layer — pile on the heavy metal bracelets. The more, the merrier!
Photo: WWD/Kyle Ericksen8/16Michelle Smith
Fashion Designer, Milly
What's your favorite back-to-school fashion memory?
When I was eleven years old, my family moved from Connecticut to rural Ohio. Back-to-school in Connecticut was always a super fun fashion moment, requiring carefully planned outfits and attention to detail. When I showed up for my first day of school in Ohio, everyone was in jeans and crummy sweatshirts, and there I was in my hot pink miniskirt, coordinating sweater, and piles of accessories. I stood out like a sore thumb and felt so self-conscious! But I pulled myself together, held my head high, and somehow got through it.
What are your first day of school styling tips?
Get dressed in your most favorite new clothes, then mess something up a little bit so it doesn't look like you tried too hard.
Photo: WWD/Thomas Iannaccone9/16Dana Lorenz
Jewelry Designer, Fenton/Fallon
What's your favorite back-to-school fashion memory?
For me it was more important to have all the outfits together for the first week than the pencils and pens and supplies, I did not care about any of that. My mother toiled more over the first seven days of school than she did all year.
What are your first day of school styling tips?
Wear a couple of things that make you really stand out, but be comfortable with yourself. As long as you're comfortable and confident and you're wearing at least one thing that's a little bit shocking, or a little bit fun, or a little bit unique to you, you'll be great.
Photo: WWD/Steve Eichner10/16Cynthia Rowley
Fashion Designer
What's your favorite back-to-school fashion memory?
The first day of school was a really big deal in my town, and I had all summer to create my outfit. To this day, I can probably describe each and every one of them as embarrassing as some of them were.
What are your first day of school styling tips?
Don't be too serious. Fashion is a way to express your creativity and individually. It's meant to be fun.
Photo: WWD/Steve Eichner11/16Steven Alan
Fashion Designer
What's your favorite back-to-school fashion memory?
I remember back-to-school was always an important time for me because I was very concerned about what I was going to wear, but I wanted it to feel like I wasn't concerned about it! It was really about finding great things that felt kind of understated, but I probably didn't even know what that meant when I was that age.
What are your first day of school styling tips?
I think you have to be within your comfort zone, so if you try to style yourself differently from the way you feel comfortable, it's not going to work. Just be yourself!
Photo: WWD/George Chinsee12/16Amy Smilovic
Fashion Designer, Tibi
What's your favorite back-to-school fashion memory?
I absolutely remember every single back-to-school outfit. I have no idea what I had for lunch today, but I can tell you every outfit going back to first grade. Sixth grade was this baby blue Oord with this navy blue pencil skirt, and the Oord had a little white collar on it. It was very chic in its own way. I loved it!
What are your first day of school styling tips?
My styling tip for anyone is to absolutely wear what you love. When people ask me, "What's a fashion don't?" Really, if you love yourself in it, I don't think it's a don't. I really think you should have fun with it!
Photo: WWD/Steve Eichner13/16Beth Buccini and Sarah Easley
Boutique Owners, Kirna Zabête
What's your favorite back-to-school fashion memory?
Sarah: We were the type of people that were waiting for the September thick Vogue to come, and all the stuff in the magazine. Collages on the closet walls! I dressed by color, like "Purple Tuesday"!
Beth: I literally every single night would get on the phone with my best friend, and we would plan our outfit out for the next day. Is tomorrow a dressy day or a casual day? Are we doing skirts or are we doing pants? Literally every night. The joke is that I was voted best dressed in my high school class, and Sarah and I were voted best dressed at UVA.
What are your first day of school styling tips?
Sarah: I always think it's a little bit weird when kids come back from the summer like, "It's a whole new different me!" Don't you remember that from high school, when people would reinvent themselves in the summer so they were barely recognizable? I think it's fun to change it up, but still be yourself.
Beth: I always had a struggle. Sarah and I are both from Virginia, so obviously when we went back to school in September, it was still full-on summer and hot as could be. I wanted to shop for fall clothes and have a fall wardrobe. But then it was so hot — you were still in summer clothes that everyone had seen in the spring! So I always tried to freshen it up and add an accessory so I had something somewhat new before November hit and we could really start wearing fall clothes.
Photo: WWD/Steve Eichner14/16Jill Stuart
Fashion Designer
What's your favorite back-to-school fashion memory?
Buying new school shoes! At the end of each summer I would always look forward to that.
What are your first day of school styling tips?
To help first day jitters, I always told my daughters to wear what made them feel comfortable and confident.
Photo: WWD/Robert Mitra15/16Simon Doonan
Creative Ambassador-At-Large, Barneys
What's your favorite back-to-school fashion memory?
I am so old — when I went to school, we had to wear uniforms! They were very strict with us about our uniforms, but we used to think of ways to make our uniforms groovy, like wearing them with flared pants. We literally would have hair inspections every week to make sure our hair wasn't touching our collar. But we found ways to be groovy! I wore Chelsea boots with my school uniform, and I thought I was just the best! Other boys would get their pants flared and wear a subtle flare, and then they would have to go see the headmaster. When people are pressed, they get very resourceful.
What are your first day of school styling tips?
I think the big tragedy of school is the conformity, where everyone wants to wear the same thing. I always beg younger kids to go for more individuality and have their own look. If you're a redhead, don't dye your hair blonde! Be glad that you're different. Celebrate, vive la difference!
Photo: Fairchild Archive16/16Billy Reid
Fashion Designer
What's your favorite back-to-school fashion memory?
BR: My mother had a women's clothing store. I remember she would bring me home shirts that were like — this was back in the '70s — quilted yokes and big collars, and I always wondered why they buttoned on the other side. Well, they were women's shirts and she was giving them to me to wear. No wonder I got teased! I was wearing a women's shirt around school all day.
What are your first day of school styling tips?
Go simple. Definitely keep it simple. And I would say wear something you've worn before. You want to be comfortable.
