Categories: Fashion

The Cutest Outfits To Wear For Your First Day Of Classes

There’s nothing worse than hearing the words “first day of classes” in the summer. To make it up to you, I’ll show you something that will make you excited for school. If planning your outfits makes you more excited for classes, here are some styles that might interest you. There’s an outfit in this list for everyone! 


1. Pretty In Plaid

Just because it’s fall, it doesn’t mean that you have to stop wearing skirts. I try to incorporate skirts into most every outfit I wear during my first week of classes. People typically dress more formal when it’s syllabus week, so a classic black skirt would be perfect for the occasion. Pair a simple skirt with a gingham blouse for a cute, studious look. Brandy Melville has a ton of similar shirts, but for a more inclusive and sustainable option, check out Etsy and Depop. I love the look of this outfit with a pair of platform oxfords and ankle length socks!

2. Lacey Layers

Lace is a very adaptable material. It can work with an elegant outfit or with a bohemian one; it can be dressed up or dressed down, depending on what you pair with it. For this outfit, I chose a more laid-back, boho look. I love the layering with the linen button-up shirt, and the crochet bag?? Incredible. I would never use a backpack again if I had a tote bag like that. Throw on some mom jeans and casual jewelry for a ready-for-class outfit. 

3. Overalls FTW

My love for overalls is ineffable. If it were up to me, I would replace every pair of jeans with denim overalls. You better believe I’m wearing a pair to the first week of classes. When matched together with a graphic tee and dad sneakers, overalls create the ideal back-to-school outfit. If you have to trudge across campus from class to class, you’ll stay comfy in this look. For those of you that love to accessorize, throw on a bucket hat or a baseball cap. Sporty and chic.

4. Beaches Or Books?

How can you let people know that you spent the summer in Nantucket without telling them? Here’s my answer to that question: dress like a coastal granddaughter. Obviously, I’m not advising you to wear a bathing suit to class. Incorporate blues, whites, and tans into your color scheme and dress in billowy clothes. Pops of bright colors are also encouraged, like the green in the picture above. If you want to go the extra mile, show off your favorite beachy jewelry. Seashell necklaces and pearl earrings never go out of style.

5. Emma Chamberlain’s Uniform

I might just be the #1 fan of Emma Chamberlain’s trademark outfit. It’s essentially just a cropped tank or shirt, a loose maxi skirt, rolled up socks, and dad sneakers. Though Emma claims this look is for the summer, I think it could work for the fall, too. Since the first week of classes is usually towards the beginning of the new season, you definitely wouldn’t freeze in a skirt and smaller top. This outfit is both casual and put-together; you’ll be sure to wow everyone in your lecture. 

6. Dress To Impress

If you’re anything like me, you struggle with matching your favorite top with the right pair of pants. Avoid mismatching by wearing a dress. A casual sundress is my wardrobe staple for syllabus week; my favorite finds are from Urban Outfitters and thrift shops. Go with a floral pattern for a romantic look, or plaid for something more academia. Remember your accessories! I love wearing dresses with dainty jewelry, and if I’m feeling it, I’ll even throw on a hair ribbon or two. 

7. Prep For Autumn

For some people, summer ends the second school begins. If that sounds like you, my guess is you love the fall. Dress for spooky season with autumnal colors, mainly browns, oranges, deep reds, and other neutral tones. Once the shorts and tank tops come off, the sweaters and jeans come on. Since it’ll probably be a bit warm out still, opt for a lightweight sweater and baggier pants. Don’t forget your pumpkin spice latte! 

8. Comfort Is Key

There’s nothing wrong with dressing for comfort. As soon as the first week of classes is finished, you bet I’m pulling out my sweatpants. My other go-to comfy outfit is an combination of neon pants and a graphic tee. I’m obsessed with my pair of pink biker shorts from Amazon and my green pair from Zara; they make a lot of appearances in my seminars. Pacsun is a great option for graphic tees, and the same goes for Etsy. Just don’t get too comfortable that you’ll fall asleep in class.

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9. Not All Business

Show your class who’s boss with this business casual outfit. While I don’t recommend wearing sunglasses to class, the sweater vest and button-up shirt combo is a must. I’m a firm believer in the sweater vest trend, even though it’s fading in popularity. (Manifesting a sweater vest comeback this fall). Chunky loafers would always fit the vibe of this outfit; I always wear my pair from Princess Polly.

10. Step Into Prep

The thought of going back to school might fill you with a very gray, very dull sense of dread. One way to fight this dread is by dressing in bright, happy colors. Be your own beckon of light in a colorful pair of pants, like these cute red gingham ones. If you’re searching for a positive mantra, find one in the form of a graphic tee. I have one that says something about the sunshine, and whenever I wear it, I can’t help but to feel all warm and cheery. Clothes really do make a person, I guess.


Half of the fun of going back to school is showing off your outfits. I feel pressured to say that the other half is learning, in case any of my professors read this. Head into your classes feeling cute and ready to ace it.

Like this article? Share it with your friends for some outfit inspiration!

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Jill Schuck

Hi everyone! My name is Jill, and I'm a senior at Trinity College in Hartford, CT. There, I'm studying creative writing and sociology, with plans to work in publishing. Aside from reading and writing, I enjoy traveling and practicing self-care. If you want to connect, follow my Instagram @jillschuck!

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