30 Back-to-School Outfits to Help You Survive the School Year

Hey guys, and happy back-to-school season—everybody’s favorite time of year! Whether you’re excited to go back to school or dreading it, here are 30 back-to-school outfits I’ve put together for you. I really tried to make them casual and actually wearable for school, and also within a dress code if you have one.

So yeah, let’s get into it!

1. Simple Jeans and a T-Shirt

We’re starting out plain and simple with jeans and a t-shirt. You pretty much can’t go wrong if you match your t-shirt with your shoes. I went for a black Van tee and some black block boots—gosh, that’s too many B’s. Now I look ready to become the honorary 4th HAIM sister, which is really my main goal in adult life. To make this outfit cozier, I’m adding an oversized denim jacket I thrifted and some green high tops for a pop of color. I like this outfit personally because it low-key looks like something that the type of guy I would have a crush on in class would wear. God, that is truly a whole new level of single—when you have to dress up as your imaginary crush in a YouTube video.

2. Corduroy Bell-Bottoms

Recently, I got these corduroy bell-bottoms, and they are majestic. It’s like having a built-in couch on your legs, and it is amazing. I added these 90s-inspired platforms that are surprisingly really comfortable to complete my funky and spunky look. Speaking of bell-bottoms, here’s an alternative outfit with the same silhouette that makes me feel like a substitute teacher, but in a hot way. Also, my legs look super long, and for once, it is not entirely because of my wide-angle lens.

3. Plaid Pants and Oversized Button-Up

For a comfier option, I swapped out my jeans for some plaid pants and went back to my Converse. A pro tip, if you like being comfortable like literally every human ever, is to get yourself some of these flowy pants because they look tailored, but in reality, they feel like pajama pants. On top, I threw on an oversized button-up I thrifted from the men’s section and left open like this pseudo jacket situation. It kind of looks like one of the smocks your art teacher would make you wear when you’re oil painting, but like a fashionable smock.

4. All-Black Outfit

All black is a really simple way to make a basic outfit look more put together. For shoes, I opted for my platform Docs to add a little bit of personality to an otherwise pretty simple outfit.

5. Overalls and Leopard Turtleneck

Oh boy, bet you didn’t think you’d be seeing overalls in 2019. These were so trendy when I was younger, and I spent all of high school trying to figure out how to wear them without looking like a farmer. Finally, this year, I got these black ones, which are minimally hillbilly-y, and I paired them with a leopard turtleneck for a funky little pop of pattern.

6. Dress Layered with a T-Shirt

Do you have a dress like this that you love but, thanks to outdated patriarchal standards, aren’t allowed to expose a part of your body that literally has no sexual function whatsoever? Yeah, if you get dress-coded for spaghetti straps, then go for the tried-and-true method of layering a t-shirt underneath. I thought this mesh one added a really cool texture, and then I finished off this goth girlfriend look with my platform Docs. For a chiller option, I went for a plain white t-shirt and then popped my oversized denim jacket on top.

7. Preppy Look with Corduroy Jacket

For my final look with this dress, I styled it in a more preppy way with this cozy corduroy jacket and some loafers. I’m just in love with this corduroy jacket because A) it’s corduroy, and I love corduroy, and B) it is so oversized—it’s basically like a glorified Snuggie. I swapped out the dress for a tank top and loose vintage shorts for a more casual look. I actually wear this outfit a lot while I’m running errands around LA, and I like how grounded and almost old-school Indiana Jones it feels.

8. Oversized T-Shirt with Witchy Boots

Back when I was in high school, people would make fun of you for wearing an oversized t-shirt because it looked like you forgot to wear pants. But recently, this seems to be the cool thing with the kiddos these days. Here, I styled a black graphic tee with some witchy boots. For a little bit more dimension, I layered this long sleeve underneath. This outfit is actually inspired by Ellie Thumann—I saw her wear something similar on her Instagram, so I wanted to recreate it. Who wore it better? Definitely Ellie, but I tried.

9. Oversized T-Shirt with Black Jeans

If you’re not a fan of the pantsless look, this outfit also works with some black jeans layered on top. I like how it’s quite a statement, even though all the pieces individually are pretty basic.

11. Striped Sweater with Plain Bottoms

Here’s another quick outfit with an oversized t-shirt. This is literally my pajama t-shirt, but as long as you add some structured boots and an oversized jacket, it looks almost convincingly like a real outfit.

10. Pajama T-Shirt as an Outfit

This is my current favorite sweater. I like stripy sweaters because they kind of do the work of creating an interesting outfit for you. Then all you have to do is pair it with some plain bottoms and shoes. These shorts are also corduroy, by the way, in case you were wondering. My corduroy obsession is a little bit out of control right now.

12. Vintage Cardigan and Pointed Heels

To dress up a simple dress, I added a vintage cardigan and some pointed heels for a very chic 50s churchgoer type look. This might be a cute option for the first day of school or when you feel like dressing up a little bit, which for me in high school was like every day because I was extra as hell.

13. Fuzzy Cardigan with Platform Docs

I took this fuzzy cardigan, tied it around my waist, and added my platform Docs for this funky 90s-inspired look. This is also perfect if your dress is a bit loose around the waist because the cardigan or flannel or whatever you want to tie around your waist cinches it in and acts like a giant fabric belt.

14. Long Straight-Leg Jeans with a Baby Tee

Recently, I’ve been seeing people rock this long straight-leg jean look. Before, everything was cropped around the ankle, but now people are getting a little adventurous and, lo and behold, covering up the ankle. I know not every school will let you show your shoulders, so this outfit would also look cute with a white graphic tee or a 90s-inspired baby tee like this one.

15. Cropped Sweatshirt with High-Waisted Jeans

In college, I was always looking for an excuse to wear sweatshirts out of the house, so I came up with this outfit. I thrifted a basic sweatshirt, cut off the bottom with scissors to make it cropped, and paired it with some high-waisted jeans and funky heart socks to make the outfit look a little bit less basic.

16. Floral Wrap Skirt with Loafers

For something more girly, I swapped out my jeans for a floral wrap skirt that’s still really comfortable because of the adjustable waist and balanced it with loafers for a preppy touch. Here’s another simple option with that same skirt. I went for a black t-shirt, tucked it in, and added these fabulously hideous platform Dr. Martens sandals.

17. Denim Jacket with Ankle Boots

To turn this summery outfit into something more fall-appropriate, I threw on my trusty denim jacket that you’re probably tired of seeing at this point—it’s been in almost every outfit—and swapped out my sandals for my favorite ankle boots.

18. Chunky Knit Sweater with Platform Docs

For my final option with this skirt, I went with a chunky knit sweater and white platform Docs to fulfill my 2012 Tumblr girl dreams. Seriously, this is what every single photo I reblogged looked like back in the day. But hey, I think it’s still pretty cute in 2019.

19. Quarter-Zip Sweater with High-Waisted Jeans

Instead of wearing a hoodie, try an equally comfortable quarter-zip. This one is from Urban Outfitters, but you can always find them in the men’s section of the thrift store. Just make sure to tuck in the front to some high-waisted jeans so you don’t lose your waist.

20. Lavender Sweater with Matching Heels

Next, I’m going for something a little bit more colorful. I have this lavender sweater and threw on some matching heels to dress it up a little bit. I feel very ladylike but still really comfortable and cozy.

21. Midi Skirt with Chunky Sneakers

Midi skirts are the perfect solution if you want something girly but also modest. I tied my sweater in the front into this kind of bulbous shape so that it would look more cropped and added some chunky sneakers to keep everything casual.

22. T-Shirt with Ruching Detail

Here’s the same thing but with a t-shirt. I really like the ruching detail on this one, but of course, if you aren’t allowed to show your midriff at school, this would also look great with a regular t-shirt tucked into the skirt.

23. White Jeans with Pastel T-Shirts

White jeans are a great option if you’re a little bored of your regular blue jeans and want to look a bit dressier. I like pairing mine with pastel t-shirts to keep the outfit looking light and summery.

24. Patterned Dress with Accessories

For something a little fancier, I’m going for a patterned dress with some white ankle boots. To me, this looks like a Pinterest-inspired outfit, so of course, I had to throw on some tortoise-shell sunglasses and a matching circle bag to complete the look.

25. Baggy Jeans with Crop Top

Here, I tried something a bit more experimental. I recently thrifted these jeans that are absolutely huge on me, but I cinched in the waist with a belt, threw on my clunky boots again, and added a crop top to balance out the baggy silhouette. I’m pretty into it.

26. Green Cargo Pants with White Sneakers

I found these green cargo pants and paired them with a white tank top and sneakers to dress down the outfit. I like that these pants are baggy and comfortable but still look tailored and trendy.

27. Vintage Shorts with Cropped Tee

Here’s another pair of vintage shorts that I think are so flattering with the pleats in the front. I added a cropped tee to keep things casual and finished off the look with my white sneakers again.

28. Flowy Dress with Belted Waist

Flowy dresses are perfect for the summer-to-fall transition. I belted mine at the waist to give it some shape and added my chunky boots for a bit of edge.

29. Denim Skirt with Long Sleeve Tee

Denim skirts are a great alternative to jeans when you want to switch things up. I paired mine with a long sleeve tee and some loafers to keep the outfit looking preppy.

30. Overall Dress with Sneakers

For the final outfit, I’m wearing an overall dress with a turtleneck and sneakers. This look is really comfortable but still has a bit of structure to it, thanks to the dress.

Hope you guys enjoyed these 30 back-to-school outfits! Remember, the most important thing is that you feel confident and comfortable in whatever you wear. Good luck with the new school year!