Heading back to school comes with all kinds of stress and excitement, including some major fashion decisions. Picking back to school outfits is a balancing act between fashion, comfort, and unpredictable weather. I know it can get a bit overwhelming, but it’s also an exciting opportunity to show off your style and maybe even take some new fashion chances.
I grew up attending schools with a strict uniform that didn’t leave much room for my personal taste. One of my favorite parts about going to college is the freedom to finally show off my personal style. I’ve loved getting to plan out outfits and wear something different every day. Still, it’s not always easy to come up with new outfits on the daily. If you’re struggling for some September outfit inspiration, here are some easy stylish back to school outfit ideas to prepare you for every single day of the month.
Day 1
Embrace the Millennial Pink Trend With A Pastel Pink Jacket and Matching Skirt
The millennial pink trend isn’t going anywhere, so you might as well embrace it for your first-day #OOTD. The pastel shade works perfect in this monochrome outfit, with even the sunglasses reflecting the rose gold light. You’ll look absolutely chic but totally on trend as you stroll into your first lecture of the semester.
Get the look: Missguided Pink Oversized Denim Jacket ($59), Free People Modern Femme Faux Leather Mini Skirt ($60), American Eagle Rose Gold Aviator Sunglasses ($10)
Day 2
Show Some Flower Power with a Floral Shirt and Baker Boy Hat
This floral shirt totally steals the show, it’s the perfect example of giving a statement piece the room to deliver. The outfit idea works because the denim skirt and black booties allow the floral shirt to shine. Top it off with an on-trend baker boy hat and grab an iced coffee on your way out the door because let’s be real, no second day of school look is complete without caffeine.
Get the look: J. Crew Slim Perfect Shirt ($98), Levi’s Deconstructed Mini Skirt ($45), Target Women’s Newsboy Hat ($13)
Day 3
Look Like a '90s Baby By Throwing a Dress Over a Tee
Channel the ‘90s and make your favorite dress school-ready by throwing a basic tee underneath. Put your hair up in a messy pony, and you’re ready to take on the city (but in reality, maybe just tackle a four-hour class).
Get the look: Forever 21 Polka Dot Mini Cami Dress ($38), Everlane The Cotton Crew ($16), Clarks Kensett Darla Oxford Pump ($70)
Day 4
Brighten Your Look With A Neon Tank and Striped Tennis Skirt
Bright colors will remind you summer is not quite over even if you have to go back to school. Experimenting with neon can be scary, but this outfit shows it certainly pays off—all eyes will be on you as you make your way across the quad. Also, don’t forget a denim jacket for those chilly September nights.
Get the look: Forever 21 Multi-Striped Denim Mini Skirt ($23), Forever 21 Ribbed Knit Crop Top ($7), Levi’s Trucker Jacket ($55)
Day 5
Pay Tribute to ‘80s Office Wear With an Oversize Blazer
Throw a blazer on to add a professional touch even to a more casual outfit. An oversize blazer is a must-have piece for your fall wardrobe as it can be dressed up or down. Paired with jeans and a crop top it’s an adorable ‘80s style outfit.
Get the look: Nasty Gal Shake it Out Plaid Blazer ($45), Romwe Cami Top ($7), Free People Straight Crop Jeans ($78)
Day 6
Add a Leather Jacket to Your Favorite Summer Outfit
I don’t know about you, but by the end of the first week of school, I’m already missing everything about summer. Make your favorite summer outfit school-ready by adding a leather jacket to a crop top and loose shorts. Some retro sunnies seal the deal and make this a perfect outfit for the transitional season.
Get the look: Forever 21 Cropped Rib Knit Halter Top($13), Boohoo Polka Dot Flippy Shorts($10), Topshop Blossom Faux Leather Biker Jacket ($67)
Day 7
Make Your Summer Dress Fall-Appropriate With Sneakers and a Button-Down
Break out with your favorite babydoll dress and pair it with a straw purse for a countryside-inspired outfit that’s both adorable and functional. Seriously, this ‘fit is great for running last-minute errands to the bookstore or hitting up the best campus coffee shop and everything in between.
Get the look: Lulus Toast to Life Mustard Yellow Mini Dress ($49), Zulily Black and White Polka Dot Tie Front Crop Top ($15), Urban Outfitters Circle Straw Crossbody Bag ($59)
Day 8
Be Brunch Ready in a Plaid Skirt and Denim Jacket
ISO the perfect look for a study break? This plaid skirt paired with a denim jacket is an easy, go-to look for brunch with the girls. The accessories such as the rhinestones socks, burgundy hat, and black bag really make this outfit feel put together—really focus on the little details like these when completing a look.
Get the look: Windsor Burgundy Boater Hat ($13), Madewell Shrunken Stretch Jean Jacket ($118), Urban Outfitters Vintage Pleated Plaid Skirt ($30), Topshop Glitter Ankle Socks ($3)
Day 9
Break the Labor Day Rule With An All-White Outfit
Ever heard that old “no white after Labor Day” rule? Throw caution to the wind and bring a touch of summer back to school with a chic head-to-toe white look.
Get the look: Topshop Jamie High Waist Ankle Skinny Jeans ($70), Urban Outfitters Anna Felt Panama Hat ($39), WERFORU Women Casual Dress Belt Genuine Leather Belt with Round Buckle ($15)
Day 10
Jump to It With a Denim Jumpsuit
Jumpsuits are perfect for styling with minimal effort, throw on a red lip for a touch of classic style. Paired with sneakers and a backpack, this is the ideal easy back to school outfit.
Get the look: Urban Outfitters Hello Sunshine Denim Romper ($69), Urban Decay Vice Lipstick ($18), Converse Chuck Taylor All Star High Top ($55), Adidas Mini Faux Leather Backpack ($65)
Day 11
Grab Coffee in Wide Leg Pants and a Crop Top
A ruffle trimmed crop top is one of those great summer pieces we hate to leave behind as the seasons change. Wear it one last time in this ensemble perfect for grabbing a coffee or taking a stroll. The wide-leg pants give off a vintage vibe while the rust-colored crossbody adds a touch of the coming fall season to a summer look.
Get the look: American Eagle Soft & Sexy Lettuce Trim Baby Tee ($25), Reformation Sailor Jean ($128), Madewell The Simple Crossbody Bag ($98)
Day 12
Beat the Seasons By Adding Tights Under Shorts
Throwing tights under shorts is a great way to make an outfit work as the weather cools down, but it’s a great way to add another detail to your look as well. A structured white jacket also bridges the gap between seasons for days when it’s freezing in the morning but boiling by lunchtime.
Get the look: Liverpool Moto Jacket ($98), ASOS Denier Black Tights ($7), Vagabond Marja Chelsea Boot ($175)
Day 13
Aim for Originality in a Bold Skirt and Red Sunnies
Don’t be afraid of bold pieces, a colorful skirt like this will be the envy of your schoolmates. Paired with a graphic tee and bright red accessories, this outfit shows you’re “original” in the best way.
Get the look: Missguided Red Multi Colored Wide Leg Striped Pant ($51), Steve Madden Editor Block Heel Bootie ($50), Urban Outfitters Wild Child Cat Eye Sunglasses ($18)
Day 14
Get Sporty in Basketball Shoes and Cargo Pants
I love street style outfits like this, and the laid-back vibe of this outfit is perfect for a long day of class. Simply combine a graphic tee with cargo pants and basketball shoes. This look is comfortable for spending hours in the library or exploring your college town.
Get the look: Extra Vitamins Waves Tee ($39), Sanctuary Terrain Cargo Pants ($99), Nike React Hyperdunk Basketball Shoes ($140)
Day 15
Break Up An All Black Outfit with Bright Accessories
This jeans-and-tank-top look is perfect for running from class to class. All-black outfits never get old, and the basic ensemble serves as a neutral backdrop for colorful accessories.
Get the look: H&M Jersey Top with Lace ($20), Everlane The Modern Boyfriend Jean ($68), Romwe Floral Print Turban ($15)
Day 16
Rock the Embellished Denim Trend With Embellished Jeans and a Peplum Top
Embellished denim is still on trend, and I love this style with the grommet detail. Paired with a peplum top, sandals, and your favorite shades, this outfit will keep you cool and stylish during those precious last few warm days spent lounging on the quad.
Get the look: Urban Outfitters Beckett Square-Neck Peplum Cami ($39), 7 For All Mankind Edie Ring-Detail Straight Jeans in Light Riviera ($239), Steve Madden Donddi Flat Sandals ($59)
Day 17
Borrow From Your Dad's Style With a Printed Button Up and High-Waisted Jeans
This dad style outfit is perfect for September’s unpredictable weather (bonus: these pieces could all be easily found at your favorite thrift shop). The printed button-up looks cute knotted or could be easily removed if it starts to heat up. It’s an easy and comfortable outfit for grabbing an early morning cup of coffee with friends or spending the day at a local park.
Get the look: Forever 21 Tropical Print Pocket Shirt ($16), Adidas Advantage Sneaker ($55), Dr. Denim Nora Light Retro ($85)
Day 18
Give off Vintage Vibes in a Cap Sleeve Tee and High Waisted Jeans
This button-up cotton shirt is an adorable vintage style basic. Paired with high-waisted jeans and platform sneakers, this is a look so easy it could be a uniform. Head to class in comfort and style with this ‘90s inspired #OOTD.
Get the look: Everlane Cotton Short-Sleeve Popover Shirt ($55), Everlane The Cheeky Straight Jean ($68), Superga COTU 2790 Platform Sneakers ($70)
Day 19
Take on the Changing Seasons in Your Favorite Layering Tops and Distressed Denim
This back to school outfit idea brings both color and pattern, and the light layers make it easy to adapt to changing weather. Plus, who doesn’t love a good pair of distressed jeans?
Get the look: American Eagle Tomgirl Jean ($60), Forever 21 Striped High-Low Shirt ($18), Missguided Pink Lace Front Long Sleeve Bodysuit ($25)
Day 20
Look Too Cool for School in a Graphic Tee and Leather Boots
Never underestimate the power of a graphic T-shirt. A vintage band tee with jeans and leather boots is the perfect “too cool for school” look. You’ll be ready to hit up a concert after class instead of hitting up the dining hall.
Get the look: Daydreamer Doors Waiting For the Sun Oversized Tee ($69), ASOS Oversized Croc Cross Body Bag ($56), Urban Outfitters Sloane Seamed Patent Ankle Boot ($79)
Day 21
Look Like a Boss in a Striped Top and Pointed Shoes
This chic business casual look is perfect for a job interview or running a club meeting. The pointed shoes and business casual top create a stylish outfit that shows you are in charge while the jeans add a touch of comfort and casual style.
Get the look: Vince Camuto Maita Pointed Toe Leather Loafer ($70), Nasty Gal Baby Be Line Striped Top ($40), Rag & Bone High-Rise Skinny Ankle Jeans ($195)
Day 22
Show Your Sporty Style With a Tennis Skirt and Windbreaker
This outfit is both functional and stylish—it’s great for running around the court at your intramural soccer game or just running around campus. The windbreaker and tennis skirt with white sneakers channel retro athleisure, the gym bag slung over the shoulder completes the look and is a functional accessory.
Get the look: H&M Pleated Skirt ($30), Nike Sportswear Funnel Neck Jacket ($80), Adidas Originals National Sling Bag ($39)
Day 23
Roll into Class in Printed Palazzo Pants and A Cropped Sweater
Palazzo pants are stretchy and comfortable for lazy days, but the bold pattern still makes a statement. Throw on a cropped sweater and you have a look that’s both easy and stylish. Finish off the outfit with neutral accessories—nobody will ever know if accidentally overslept.
Get the look: Boohoo Woven Flamingo Print Wide Leg Trousers ($18), Tobi Jeannie Black Lace Up Crop Sweater ($23), Rebecca Minkoff Small Vanity Saddle ($123)
Day 24
Hit the Books in Style with A Dressed Down Jumper
This outfit makes me rethink what I define as business casual. The pinstriped jumper keeps things professional while the off the shoulder top shows personal style. It’s the perfect outfit for heading to work or the library.
Get the look: Forever 21 Plunging Linen Blend Jumpsuit ($28), Free People Smocked Crop Top ($38)
Day 25
Mix and Match Printed Pieces to Create A Unique Outfit
This is certainly an outfit that shows you’re not afraid to take some fashion risks by mixing patterns. Try combining some neat thrifted pieces and put together your own original ensemble.
Get the look: Zara Patchwork Print Pants ($36), Le Specs x Adam Selman The Last Lolita ($119)
Day 26
Show Off Your Sophisticated Style With an All Black Outfit And a Duster Jacket
Throwing a dressy duster over an all-black ensemble will create a sophisticated look for a day exploring museums or meeting a dinner date. The reflective sneakers add a touch of texture to an outfit that’s both classy and functional.
Get the look: Keds Triple Kick Metallic Suede ($68), BooHoo Waterfall Duster ($18), Banana Republic Leather Trouser Belt ($48), Topshop Black Mom Jeans ($75)
Day 27
Dress Down a Sheer Top with a Black Slip and Sneakers
Make your favorite sheer top campus-appropriate by pairing it with a basic black slip. Throw on some sneakers for comfort, and you have a look that’s perfect for hitting the books or the dance floor.
Get the look: Free People Pop It Layering Tee ($40), Urban Outfitters Cami Slip Mini Dress ($30), Vans Old Skool Platform ($55)
Day 28
Have a Picnic in Black Jeans and Polka Dots
Polka dots take this basic, color-blocked outfit to the next level. In a red blouse paired with black jeans and boots, you’ll be ready for a school day or a picnic, but throw on a red lip and you’ll be ready for a night out.
Get the look: Topshop Polka Dot Tie Front T-Shirt ($50), American Eagle Mom Jean ($40), Automatic Leather Chelsea Boots ($51)
Day 29
Be a Style Scholar in Trousers and Wide Frame Glasses
This look comes off both casual and professional by combining dress pants, a graphic tee, and wide frame glasses. Adding details like a cinched belt and glasses to the outfit will help you look stylish and sophisticated, even if you’re struggling at a study sesh.
Get the look: Everlane Italian GoWeave Easy Pant ($88), Vagabond Olivia Leather Boot ($160), Warby Parker Chamberlain Frames ($95), Skagen Lobelle Leather Saddle Bag ($195)
Day 30
Go Beyond Basic Black and White with Embellished Black Pants
This black and white outfit is anything but basic. The embellished detail in the pants adds a level of texture, while the baker boy hat adds a touch of vintage to a more modern look. This look will take you from class to a night out at your favorite restaurant in style.
Get the look: Missguided Black Button Detail Flared Pants ($13), ASOS High Crown Wool Baker Boy Hat ($26), Free People TGIF Pullover ($68)
Now that you have your first-month outfits sorted, click here for some perfect-for-class shoes to wear for those long walks across campus.
Opening image by Chloe Felopulos.
