plaid skirt fall back to school outfit

6 Chic Back to School Inspired Outfits

By
Carolyn Arentson
Last Modified on July 27, 2019

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My school days are far behind me, but that doesn’t mean I can’t jump on the back to school outfits train! Though summer is fun and grand, I welcome fall and all the styles that come with it. Though I’m not a hoodie and birks type of girl, I do like plaid, blazers, and boots! So here’s my take on some chic back to school outfits!

6 Chic Back to School Outfits

1. plaid skirt + cropped cardigan + otk boots + headband
Starting out strong with a total Gossip Girl outfit. Just on the waiting list for Constance! And hopefully, Blair will let me sit on the steps since I’m wearing a headband! Too many GG jokes? Yeah, I agree. 😉

Related: The 5 Piece Fall Outfit

skirt | cardigan | headband | glasses | boots (Rue21, similar)

2. plaid pants + turtleneck + sneakers
Plaid is all around a good idea, whether the print is in a skirt, pants, or dress! This look is casual and cute when paired with sneakers. Totally works too if you’re actually wearing this for school!

Related: 1 Super Easy Fall Boot Hack

pants (tjmaxx, similar) | turtleneck (kohls, similar) | sneakers (target, similar)

3. plaid dress + socks + sneakers
As if a plaid dress with sneakers wasn’t cute enough…just add some socks and this look is playful and fun! Fake glasses optional 😉

Related: 7 Fall Outfits That Will Never Go Out of Style

dress | glasses | sneakers (target, similar)

4. denim skirt + graphic tee + loafers + beret
Denim skirts are classic pieces and ones that can be dressed in whatever mood you’re feeling. Go the stylish fall route with loafers, a plaid blazer, and a beret! The graphic tee adds a little punch to this look!

Related: Staples You Need to Prep Your Wardrobe for Fall

blazer | denim skirt (similar) | loafers | beret (similar) | tee

5. plaid skirt + turtleneck + loafers + baker boy hat
You’re noticing a theme, right? Plaid is best! No matter your age or whether you’re actually going back to school or not, plaid is a print you can count on for fall. This look has a little Parisian flair too that you know I can’t say no to!

Related: 20+ Super Cute Fall Outfits

loafers | turtleneck (kohls, similar) | skirt (Forever 21, similar) | hat (similar)

6. tights + black skirt + gray polo + boots
Tights have been off the scene for what seems like forever, and they’re going to be coming back this fall! Sure, in bold colors, but I like black and the little bit of texture this pair brings! A polo gives that preppy twist to this back to school look too.

shirt | skirt | tights (similar) | boots (similar) | headband

Do you like preppy and/or chic back to school looks? What’s your favorite look out of these? Let me know!

And if you are one of these people that hate it when people move on to fall so quickly…well sorry not sorry 😉

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33 Comments

    1. So many amazing options you have laid out here, it’s hard to choose!! ? I really like that jean shirt with the graffiti, and the loafers etc ? Very unique & just screams funky + chic!
      Xx, Morgs*

  1. The plaid pants and sneakers was my favorite of these finds. I sometimes wish I was heading back to school so I could create these fun looks. I am excited that denim skirts are back, they are so fun.

  2. The intro to that first outfit had me giggling so hard. Gossip Girl references are the way to my heart – and yes, Blair would LOVE that look! And I love all the rest of them just as much as the first. You’re giving me some serious inspiration for plaid and blazers and mini skirts!

    1. I didn’t even think about Clueless. I was thinking all Gossip Girl, but I like the reference!

    1. Haha I’d miss school if it were a place that people actually dressed up 😉

  3. You’ve got such great style! I don’t think I looked nearly this good at college!! Mostly athleisure for me. I adore the denim skirt and blazer outfit!!

  4. Wow these are really cool and chic outfits for going back to school. I loved skirts from Forever 21.