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One minute it’s summer break, the next minute you’re frantically wondering what to wear to the first day of school. Whether it’s about walking into high school with confidence or just getting through the day without a meltdown, these back to school outfits bring the cute, comfy, and “I’ve got this” energy we all need when the school year kicks off.
Oversized Hoodie and Puffed Crop Vest
Shop this Amazon Outfit HERE (This vest has limited size options, shop here for a similar style.)
Effortless, an oversized hoodie and leggings are an easy fix for a running late but still looks good outfit. Add on platform booties and a crop vest for a trendy first day of school look.
Crop Tee and Flared Ribbed Pants
Stay cute and casual with an oversized crop tee and flared knit pants that move with you. Finish it off with sneakers and a crossbody for a comfy high school look.
Fleece Vest and Oversized Sweater
An oversized sweater and fuzzy vest are the ultimate duo for cozy layering. Add leggings and some comfy slippers that give Ugg vibes for a relaxed school year outfit.
Baggy Wide Leg Pants with Tube Top
Baggy wide leg pants with a ruched tube top are easy to wear for the beginning of the school year, where the mornings are cool and afternoons grow humid. Just slide on some comfy sandals and you’ll be out the door in five!
Athletic Dress and Running Shoes
Shop this Amazon Outfit HERE (these sneakers since sold out, shop here for a similar style)
Perfecting for sprinting to class or just looking like you might—this athletic dress with a built-in bra and pockets is practical for high school. Throw on running shoes and call it your easiest last-minute sporty outfit yet!
Sleeveless Tennis Dress and Chunky Sneakers
Athletic meets chic with this sleeveless tennis dress. I paired it with some Hokas, making this is an easy high school outfit that works on and off the court.
Square Neck Tank and Mini Skort
Throw on a relaxed fit denim jacket and sandals with a buttery soft square neck tank and matching skort to handle the unpredictable weather at the beginning of the school year.
Spaghetti Strap Tennis Dress with Denim Shirt
For a sleek look, a spaghetti strap tennis dress pairs perfect with a lightweight, denim button down shirt. To give balance, just add a vintage shoulder bag and slip on sandals.
Lounge Set and Suede Clogs
Serve relaxed but make it fashion with this cute two-piece set that feel like pajamas but totally look put together. Top it off with suede clogs for a comfy vibe that works beyond just the first day of school.
Long Sleeve Mini Dress and Sneakers
This square neck dress is and flattering, and I rounded out the look with my go-to pair of sneakers.
Flare Mini Dress and Striped Shirt
Shop this Amazon Outfit HERE (These sneakers since sold out, shop here for a similar style)
Layer up with a striped button down over this short sleeve mini dress that keeps you chic from first bell to last. Add a shoulder bag and some sneakers to keep it casual.
Ribbed Tank and Plaid Shorts
A classic ribbed tank and comfy gingham lounge shorts with buckle sandals are perfect for those still-summer mornings at the start of the school year. You can always layer with a denim shirt if the classroom A/C is cranked too high.
Off-Shoulder Top with High-Waisted Jeans
Shop this Amazon Outfit HERE (these jeans have since sold out, shop here for a similar style)
A sleek off-shoulder top is a great option to stay cool but covered during those first few back to school weeks. Finish the chic but casual look with platform boots and high-rise denim jeans.
Short Sleeve Lounge Set and Platform Ankle Boots
I love a cute and simple lounge set. All you need is your fave pair of bootie and a soft hoodie to stay comfy all day.
Oversized Off the Shoulder Sweater with Relaxed Fit Jeans
Shop this Amazon Outfit HERE (these jeans have since sold out, shop here for a similar style)
Those breezy fall days will be the least of your worries with this soft and chic off-shoulder sweater. Slip on some straight leg jeans and these furry clogs for the ultimate cozy back to school look.
Cable Knit Sweater with Soft Leggings
I’m obsessed with this chunky knit sweater and leggings combo. Just grab a saddle bag and comfy slip-on shoes for a classic high school outfit.
Fitted Crop and Linen Pants
Light, breezy, and seriously cute, these chic linen pants paired with a crop tee and some Converse gives all the laid-back energy to start the school year off right.
Oversized Sweatshirt with High-Waisted Leggings
This is a go-to high school outfit for those “just trying to survive the day” vibes. Wear an oversized GAP sweatshirt with leggings and Hokas for all-day comfort without looking like you rolled out of bed.
Denim Jacket with Palazzo Pants
A crop top with palazzo pants makes a cute and simple outfit to wear on repeat throughout the school year. To elevate the look, a denim jacket and a crossbody bag.
Trench Coat and Straight Leg Jeans
A trench coat is a chic, versatile piece that can be dressed up or down. I love pairing a trench with a simple pair of jeans and comfy sneakers for a casual but cute outfit for high school.
Waffle Knit Lounge Set with Slippers
The soft waffle knit shirt and matching flare pants keeps you warm and cozy. All you need is a pair of slippers to stay cozy on rainy days during the school year.
Sweatshirt and Suede Ankle Boots
Comfort is key for the cold months of the school year. A baggy sweatshirt and leggings with your go-to ankle boots is a cute and simple outfit for high school.
Cropped Zip Up Hoodie with Leggings
A cute cropped hoodie is essential for you fall high school wardrobe. It’s so versatile, you can layer it with a super soft crop tank and leggings for the perfect last-minute look.
Fleece jacket and Cropped Cami
This look is peak cozy chic! Perfect for fall and winter days of the school year, the fuzzy jacket keeps me warm throughout the day. Round out the outfit with a cropped cami and a pair of Converse.
Crochet Sweater Vest and Jeans
A crochet buttoned vest and straight leg jeans is a chic throw-on-and-go-outfit. Finish the look with your fave pair of sneakers for a casual high school look that still makes a statement.
Trench Coat with Leggings
Keep it sleek and simple with this square neck tank and leggings duo. Top it off with a trench coat for a cool without trying kinda vibe that you can rock throughout the school year.
V-neck Vest with Cropped Denim
Add a little vintage flair to your school year wardrobe with a knit vest top and cropped jeans. Finish it off with buckled sandal slides for an easy, breezy style for those warmer days of school.
Baggy Crop Tee and Linen Wide Leg Pants
After a late night of studying and little sleep, make your test day low-key with a loose crop tee and lightweight pants. It’s a comfy high school outfit that still looks intentionally chill.
Seamless Jumpsuit and Long Knitted Cardigan
This outfit is lazy day perfection that till comes off put together. Layer a cozy oversized cardigan over a seamless jumpsuit and complete the look with suede ankle boots.
Batwing Sweater with Leggings
You can never go wrong with a chunky sweater and soft leggings! Just add a pair of platform ankle boots to elevate the look while still staying comfy for a day full of classes.
Cropped Tee and Joggers
For those zero effort but still cute days, throw on joggers with a fitted crop tee. A subtle sporty look for the school year without wearing over-the-top athletic wear.
Ultra Soft Lounge Set
When you want to feel like you stayed in bed all day, but still put together, this comfy lounge set is the answer.
Tennis Dress with Sweatshirt
I love how this high school outfit brings all the old money energy but keep it casual. A spaghetti strap tennis dress paired with an oversized sweatshirt, perfect for those days of school where the mornings are chilly but afternoons grow hot.
Long Sleeve Crop and Flare Jeans
This is a practical back to school outfit you can wear throughout the school year. All the throwback vibes, you can’t go wrong with a ribbed scoop neck top, high-rise flares, and a pair of Converse.
Blazer with Fitted Tank and Relaxed Denim
Take casual up a notch with a matching fitted crop and blazer—equal parts polished and laid-back. Pair it with denim and a saddle bag for a chic, easy outfit made for the school year.
How to Pick a First Day of School Outfit
- Pick Comfort first: Stick with soft fabrics and versatile pieces you can wear on repeat and feel good in all day
- Add One Statement Piece: A fun jacket, cool sneakers, or a cute bag can totally level up a simple outfit. Want expensive style without the price? Check out these designer lookalikes.
- Plan for the whole day: Think beyond the first photo—will it survive gym class, lunch, and a full day of running around? Layers and comfy shoes are always a smart move.
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