Wondering what to wear on the first day of high school? These 35+ back to school outfits are perfect looking your best!
Starting high school can be a nerve-wracking experience, and choosing what to wear on the first day can add to the stress. However, dressing well can help you feel more confident and ready to tackle the day ahead. With so many outfit options available, it can be challenging to decide what to wear.
That’s why we’ve put together a list of 35+ back-to-school outfits to inspire you and help you make a great first impression. From casual to dressy, these first day of school outfits are perfect for the first day of high school and beyond. So, let’s dive in and find the perfect outfit for you!
Styles For Every Personality
In the first part of those post, I’ll break down what to wear on the first day of high school based on your personality and style!
If You Like…Pastels, Flowers, & Nice Things
If you’re a fan of pastel colors, flowers, and all things pretty, then you might want to consider the Pastel Y2K and preppy styles. Pastel Y2K is a maximalist style that includes a wide variety of pieces, making it difficult to generalize. The key is to add as many accessories as you want, such as big hoops, cute statement earrings, clay pendant keychains, furry cardigans, and colorful baguette bags. To achieve a “chill” look, you can also try out the 2000s Juicy suit trend.
For a preppy outfit, you can start with a white, long-sleeved button-down shirt and layer it with a knitted pastel vest. Finish off the look with loafers or white sneakers. When it’s warmer, you can swap out the white shirt for a pastel or vibrant-colored collared shirt.
If you prefer a smaller bag, a baguette bag is a great option. For larger items like books and notebooks, a white tote bag or neutral-colored backpack is both practical and stylish. This combination works well in any situation!
Staple Pieces:
- Baby Tees
- Pastel Cropped Tops
- Pastel Vests
- Argyle Vests
- Tube Tops
- White Button Down
- Collared T-shirts
- White Sneakers
- Pastel-colored Crocs
- Loafers
- Baguette Bag
- Canvas Tote Bag
Check out more of our favorite Y2K outfits here.
One of my favorite pastel combos is purple and yellow because of their soft contrast. With the mini skirt and the sweater, this outfit would great during the summer – especially if your high school’s rooms are airconditioned.
Get ‘Pretty in Pink’ vibes from this bestie outfit! Preppy ’80s style would be the best way to describe this fit. Their Jordans also contributed a nice color-block accent to their whole look. To give your usual vest fit a little oomph, tuck or crop them like this!
This outfit reminds me of strawberry jellies, tulips, and candy! The pieces she picked, the long-sleeved collared knit top, pants, and socks also look so comfortable (apart from stylish), which is appropriate for studying or learning.
A great way to use jeans is by turning them into an ice breaker piece, an opportunity for negative space. This allows other colors and main pieces to stand out and gain interest. Look how the sweater, purse, and shoes stand out with this dull bleached pants.
Here’s another relaxed and laid-back version of the first fit. Fuzzy dual-toned crop top, lilac high-waisted cargo pants, and espadrilles. A couple of necklaces can also add a bit of accent to this soft outfit.
Want to romanticize your life? It’s your time to shine with an all-pink outfit! Rock this fit with a fitted cropped basic, a pink knit sweater, and a matching mini skirt! To make it “school-appropriate”, switch up the heels for sneakers or chunky loafers.
If You Like…Grunge, Indie Music, & Digital Art
If you’re a fan of grunge, indie music, and digital art, then there are several styles you might want to try out for your back to school outfits, including minimalist grunge, biker chic, and rock ‘n’ roll.
Minimalist grunge is all about 1990s style, featuring bumsters, Canadian tuxedos (or denim jackets), staple white t-shirts, and Doc Martens. You can take inspiration from icons like Kate Moss, Fiona Apple, and Janet Jackson.
Biker chic fashion is similar to minimalist grunge but with an edgier twist. Studded leather jackets, leather leggings, combat boots, distressed denim jeans, and chrome jewelry are some of the staple pieces of this style.
Rock ‘n’ roll style is also similar to the first two styles, but it’s focused on aged, distressed, and vintage clothing. To achieve this look, you can start with tie-dyed tees, cut-out Bermuda shorts, tank tops, vintage band shirts, and ripped jeans.
Overall, these styles are perfect for anyone looking to channel their inner rebel and express themselves through fashion. Whether you prefer minimalist grunge, biker chic, or rock ‘n’ roll, there’s a style out there for you.
Staple Pieces:
- Low-waisted Jeans or Dad Jeans
- Washed Black Denim Jeans
- Canadian Tuxedo or Denim Jacket
- Staple White T-shirt
- Tie-dyed T-shirts
- Vintage Band Shirts
- Cropped Tank Top
- Cut-out Shorts
- Leather Jacket
- Leather Leggings
- Ripped/Distressed Jeans
Check out our favorite grunge fashion brands here.
Nothing describes the ‘90s better than denim on denim! Look at how this Canadian tuxedo paired with matching jeans. I love how polished and clean the seams look as well.
If you’re going for a smart bur relaxed first day look, put on your favorite white tee, blazer, and bleached denim jeans. To tone down the blazer, wear your go-to canvas sneakers.
Be that chic girl-next-door by wearing your denim midi skirt with suede boots. To create a slim, cinched waist, pair with a fitted long-sleeve turtleneck top. For a feminine touch, wear hoop earrings.
If 1990s is too straightforward or serious for your taste, you can incorporate the Y2K silhouette while retaining 1990s elements like denim and monochrome pieces.
Keep it simple and polished with a Parisian chic-minimalist grunge outfit. Instead of pants, switch up with something more feminine, like this denim mini skirt. This may not be comfortable for daily wear, but its great for looking your best on the first day of high school.
If You Like…Libraries, Journalling, & Poetry
If you’re a fan of libraries, books, coffee, journaling, and literature in general, then you might want to consider dark/light academia styles and cottagecore styles for what to wear on the first day of high school.
Dark academia is a subculture centered around poetry, arts, writing, and higher education. This style features vests, pleated skirts, button-downs, turtlenecks, and “fall” style clothing. The color palette for this style is typically darker, consisting of navy blue, dark brown, dark purple, burnt orange, and olive green. Light academia follows a similar style but with a lighter color palette, usually consisting of brown, beige, and cream white. European university students are a great reference for this style. A tote bag or a canvas backpack is a great complement to this style.
For a softer version of lit. chic, you can go with cottage core or romantic/soft feminine. Skirts, puff-sleeved tops, corset tops, and dainty floral dresses paired with canvas sneakers or Mary Janes can give you a cohesive foundation for these back to school outfits.
Overall, these styles are perfect for anyone who loves literature and wants to express their passion through fashion. Whether you prefer dark or light academia or cottage core, there’s a style out there for you to wear on the first day of high school.
See more about dark academia style here.
Staple Pieces:
- Vests
- Pleated Skirts
- Button-downs
- Turtle Necks
- Puff-sleeved Tops
- Scarves
- Layered/Tiered Skirts
- Ruffle Dresses
- Floral Dresses
- Corset Tops
- Loafers
- Canvas Sneakers
- Mary Janes/Doll Shoes
- Ballet Flats
Dark academia is a great representation of literary and art enthusiasts. There’s no better foundation than a vest, a button-down, and a pair of high waisted plaid pants. Add a belt for a nice accent.
If you want to keep it minimal, straightforward, and easy to put on, just put on an all-black fit and add an accent cardigan piece. A pair of black ankle boots can create a seamless fit.
When the summer’s end is approaching, layers are in! Put on a turtleneck top as foundation, and add a button-down polo for dimension. Applying the all-black fit + accent cover up works for this ensemble as well.
If a button-down feels too formal or masculine for your taste, a great way to add a feminine touch is by switching it up to a puffed sleeve button-down blouse. Add a plaid dress to create dimension and character.
How to dress for a rainy first day of high school: wear a white button-down, overlap an argyle vest, and wear a matching jacket over it. Blue jeans can add contrast to this warm-toned outfit.
On the other hand, you can dress like cappuccino in white, cream white, brown, and a coffee-toned knitted vest. For an added contrast/accent, painting your nails in vibrant red would be fabulous!
Not a fan of layers? Keep it minimal and stylish by wearing few pieces in contrasting colors. This creates dimension — even without the extra pieces. Color blocking neutral pieces would work well too!
If You Like…Techno/Hip-Hop Music, Socializing, & Extreme Sports
If you’re into techno/hip-hop music, socializing, and extreme sports, then you might want to consider Y2K space-age fashion, Gorpcore or utilitarian, or hip-hop street-style fashion for what to wear on the first day of high school.
Y2K space age fashion is all about leather, PVC, and chrome fabrics. To wear these materials to school, it’s important to incorporate them into an outfit rather than going all out. A black dress, skirt, or pair of pants are great foundation pieces. You can add chrome/silver accessories, from your bag to your jewelry, and pair them with sneakers like ‘dad sneakers’ or sporty-casual sneakers from New Balance and Asics.
Gorpcore is all about utilitarian clothing, featuring cargo pants, Goretex waterproof sneakers, puffer jackets, fisherman vests, and combat boots. It’s a genre of fashion that’s secretly comfortable because you’re wearing practical clothing. If you enjoy outdoor activities, knowing how to style your utilitarian pieces can save you from buying a whole new wardrobe.
Hip-hop street style is a subversive and experimental style that can be paired with a hoodie and blazer or a skirt and sporty/utilitarian top. Footwear can vary, but sporty sneakers and canvas sneakers are great investments for this style.
Overall, these styles are perfect for anyone who loves techno/hip-hop music, socializing, and extreme sports. Whether you prefer Y2K space-age fashion, Gorpcore or utilitarian, or hip-hop street-style fashion, there’s a style out there for you to wear on the first day of high school.
Staple Pieces:
- Chrome/Silver Jewelry
- Black Skirt
- Black Dress
- Black Pants
- Leather Jacket
- PVC Pants
- Puffer Jacket
- Fisherman’s Vest
- Grey Hoodie
- Black Blazer
- ‘Dad’ Sneakers
- Canvas Sneakers
- Waterproof Footwear
Gorpcore challenges conventional silhouettes with oversized utilitarian pieces. This outfit consists of a workwear jacket, cargo pants, clogs or chunky boots, and a pair of “Spyder” sunglasses.
If you’re feeling experimental, try finding a pair of oversized cargo jeans in the men’s section. Do necessary alterations to fit in it perfectly.
Nothing beats a mini skirt when going for a feminine gorpcore look! To complete this back to school outfit, pick chunky footwear or utilitarian footwear with socks for a bulky silhouette.
Nothing beats the comfort of midi skirts, especially when worn with back to school outfits. Find an accent skirt to pair with a beloved classic tank top and shoes (with white socks). Laid-back and head-turning!
Gorpcore or utilitarian isn’t always limited to dark or monochrome colors for your back to school outfits. See how she played with pastel colors and brown tones to balance out her outfit.
Flaunt that cool girl energy with this a black cropped top, leather jacket, cargo skirt, and chunky low-cut boots. Pair with an embellished baguette bag for a Y2K touch. This is one of my favorite edgy back to school outfits!
If You Like…Meditation, Adventures in Nature, & Crystals
If you’re into meditation, adventures in nature, and crystals, then bohemian style might be the first thing that comes to mind. However, there are similar but progressive styles that fall under this category. For what to wear on the first day of high school, you might want to consider minimalist zen style/Wabi-sabi style, fairycore, or bohemian.
Minimalist zen or Wabi-sabi style is all about minimal clothing made of natural materials like linen, cotton, or crepe fiber. This style features airy button-downs, linen skirts/pants, and Kimono cover-ups that are both comfortable and great for studying or hanging out in the library.
Fairycore or Fairyfolk is similar to cottagecore but with a bit more embellishment and extra details. This style features soft pastel colors, mushroom embellishments/accessories, gauzy dresses, and floral details. For school, you can tone it down by pairing a dressy top with jeans.
Bohemian style is a bit more maximalist and crazy about prints, featuring printed tiered skirts, tube/bandanna tops, and fringed jeans. For school, it’s important to keep it comfortable and appropriate for a learning environment or dress codes that might be required in your high school.
Overall, these styles are perfect for anyone who loves meditation, nature, and spirituality. Whether you prefer minimalist zen style/Wabi-sabi style, fairycore, or bohemian, there’s a style out there for you to wear on the first day of high school.
See also:
Staple Pieces:
- Mushroom Earrings
- Kimono Cover-up
- Linen Button-Down
- Linen Pants
- Puff-Sleeved Top
- Floral Dress
- Crochet Tops
- Printed Tiered Skirt
- Kerchief Bandanna Top
- Granny Square Tote Bag
- Canvas Tote Bag
- Loafers
- Clogs
- Open-toed Slip-on Sandals
Choosing soft, simple, and minimalist pieces is the best way to emulate a clean zen look for your first day of high school outfits. Pick a white basic tank top, a neutral cardigan, and dainty ballet flats to get this look.
I love how this look replicates modest Japanese street styles! The long-sleeved top, the jumper dress-like cover up, and pants just defined dimension to a whole new level!
Taking colors from nature is enough to create a soft look, despite the darkness of the color’s tones. Take for example this earthy brown skirt paired with black.
Sage green is one of my favorite colors to play with when wearing zen first day of school outfits. Paired with cream white, it looks so easy on the eye! For full-on comfort, wear white sneakers.
When in doubt, wear linen. Linen is airy, light, and comfy, and it gives beach-like energy no matter what you pair them with.
Pleats create dimension and character to any outfit, especially if you’re planning to do layering. This isn’t exactly a simple or minimal outfit, but the colors blend harmoniously with each other.
Don’t be intimidated to go all white! To tone down a bright dress like this, you can wear loafers instead of heels. A feminine dress like this doesn’t have to wait for special occasions to be worn!
Go fairy core by wearing a dressy piece with casual accents. I particularly love the arm warmers with this dress! The witchy jewelry also popped, being the darkest piece in this outfit.
FAQs About What To Wear On The First Day Of High School:
Here are some common questions about the top cute back to school outfits!
How can I find the perfect back to school outfit that fits my personal style?
To find the perfect back to school outfit that fits your personal style, start by considering your interests, body type, and comfort level. Look for inspiration online, try on different styles and colors, and don’t be afraid to mix and match.
What should I consider when choosing a back to school outfit?
When choosing a back to school outfit, consider the dress code, your personal style, the weather, and your comfort level. Choose clothing that makes you feel confident and comfortable, while still adhering to school rules.
Are there any trends in back to school outfits this year?
Some trends in back to school outfits this year include oversized blazers, denim jackets, plaid skirts, chunky sneakers, and statement accessories.
How can I make my first day of school outfits comfortable and practical for a long day of classes?
To make your back to school outfit comfortable and practical for a long day of classes, choose clothing made of breathable materials, wear comfortable shoes, and consider layering to adjust to changing temperatures.
Should I stick to dress codes when choosing back to school outfits?
Yes, it’s important to stick to dress codes when choosing a back to school outfit. Check your school’s dress code policy and choose clothing that meets the requirements.
What are some affordable options for back to school outfits?
Some affordable options for back to school outfits include shopping at thrift stores, buying basics from fast fashion retailers, and looking for sales and discounts.
Can I wear the same back to school outfit multiple times or should I have a different outfit for each day?
You can definitely wear the same back to school outfit multiple times, but it’s also fun to mix and match different pieces to create new outfits.
How can I accessorize my back to school outfit to make it stand out?
To make your back to school outfit stand out, consider adding statement accessories like jewelry, hats, scarves, or bags. You can also experiment with different textures, patterns, and colors to create a unique look.
Where can I shop for cute back to school outfits?
When shopping for back to school outfits, there are many options available to you. Department stores like Macy’s and JCPenney offer a wide variety of clothing options, from basics to trendy pieces. Fast fashion retailers like H&M, Forever 21, and Zara are also popular choices for back to school shopping, as they offer affordable and stylish clothing options that are updated frequently.
Thrift stores are another great option for finding unique and affordable back to school outfits. You can often find vintage or retro pieces that are on-trend, as well as basic items like t-shirts and jeans. Shopping at thrift stores is also an eco-friendly option, as it reduces waste and promotes sustainability.
Online marketplaces like Amazon and eBay are also great places to shop for back to school outfits. You can find a wide variety of clothing options, as well as accessories and shoes, all from the comfort of your own home. Online marketplaces also often offer discounts and deals that you may not find in-store.
In addition to these options, you can also consider shopping at local boutiques or checking out online marketplaces like Etsy for unique and handmade clothing. Whatever your budget or personal style, there are plenty of places to shop for back to school outfits.
Should I dress up or dress down for my first day of school?
It depends on your personal style and the dress code of your school. If your school has a more formal dress code, you may want to dress up a bit more. If your school has a more casual dress code, you can dress down a bit. Ultimately, it’s important to wear something that makes you feel confident and comfortable.
What are some classic first day of school outfits that never go out of style?
Some classic first day of school outfits include a simple t-shirt and jeans, a collared shirt and khakis, or a dress with flats. These outfits are timeless and can be dressed up or down depending on your personal style.
Should I wear something comfortable or something trendy on my first day of school?
It’s important to strike a balance between comfort and style on your first day of school. You want to wear something that makes you feel confident and comfortable, but also shows off your personal style.
Choosing what to wear on the first day of high school can be a daunting task, but it doesn’t have to be. By considering your personal style and interests, you can find back to school outfits that makes you feel confident and comfortable. From minimalist zen style/Wabi-sabi style to bohemian and fairycore, there are plenty of first day of school outfits to choose from. So, whether you prefer a more classic look or something a bit more trendy, take some time to explore your options and find the perfect outfit for your first day of high school.
