plaid skirt fall back to school outfit

6 Chic Back to School Inspired Outfits

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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. 😉

plaid skirt fall back to school outfit

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!

plaid pants fall back to school outfit

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 😉

plaid dress fall back to school outfit

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!

denim skirt and plaid blazer fall back to school outfit

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!

plaid skirt fall back to school outfit

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.

tights look fall back to school outfit

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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6 back to school outfits


Founder and editor of My Chic Obsession, Carolyn is your trusted fashion maven. Carolyn's drive to help others achieve a classic and timeless wardrobe fuels her posts, making a go-to resource for style seekers worldwide. Beyond the wardrobe, she resides in the heartland of the Midwest, dreaming up new ideas and raising her two lively boys - her biggest fashion critics.