stylish high school student in school hallway

Back to school outfits

5 school outfit fails and what to do

By Mia Thompson

Published: 17 May 2025

“Fashion is what you buy. Style is what you do with it.” – Unknown. This quote kinda sums up school outfits, don't you think? It’s not about having the latest trends but making them work for you. So, let's dive into some common school outfit fails and, more importantly, how to totally rock your school style!

The 'I Rolled Out of Bed' Look (and How to Avoid It)

Okay, we've all been there. The alarm didn't go off (or you snoozed it...five times), and suddenly you're scrambling. The result? A look that says, 'I wrestled with my closet and the closet won'.

  • The Fail: Mismatched everything, wrinkled clothes, and hair that resembles a bird's nest. I remeber one time walking into class with two different shoes. Talk about embarrassing!

  • The Fix: Plan ahead! Seriously. Even just thinking about what you'll wear the night before makes a HUGE difference. Pick out a simple outfit that you know looks good on you. And for those mornings when you really can't, a classic hoodie and jeans combo is always a safe bet. Add a baseball cap to hide the bedhead! I even keep a spare toothbrush and hairbrush in my backpack for emergencies.

student with messy hair running late for school

student with messy hair running late for school | Image: Supplied

The 'Trying Too Hard' Ensemble

This is the opposite of the 'rolled out of bed' look. It’s when you're so focused on being fashionable that you end up looking… uncomfortable.

  • The Fail: Sky-high heels (in the hallway?), a dress that's more suited for prom than algebra, and enough makeup to stop traffic. Trust me, it’s not the vibe.

  • The Fix: Keep it simple and age-appropriate. School is for learning, not for competing in a fashion show. Focus on comfortable, practical pieces that reflect your personality. A cute top, jeans, and sneakers can be just as stylish as a mini-dress and heels, especially if you add some fun accessories like a cool watch or some funky earrings. When I go to school, I always try to keep it simple to not get too much attention from other people.

teen girl overdressed for school

teen girl overdressed for school | Image: Supplied

The 'Lost in the Laundry' Look

This one is all about fit... or lack thereof. Think clothes that are either way too big or so tight you can barely breathe.

  • The Fail: Baggy jeans that drag on the floor, a t-shirt that's practically a dress, or leggings so tight they cut off circulation. None of these are good ideas, trust me. I once saw a girl whose jeans ripped right down the seam during math class. Awkward!

  • The Fix: Know your size (and buy clothes that fit!). This sounds obvious, but it’s amazing how many people wear clothes that are the wrong size. Pay attention to how clothes feel and look on your body. Don't be afraid to try things on before you buy them, and consider getting items tailored if necessary. A well-fitting outfit will always look better than something that's too big or too small. I feel like a million bucks when I am wearing an outfit that fits me well.

teen girl wearing oversized clothing

teen girl wearing oversized clothing | Image: Supplied

The 'Walking Billboard' Disaster

We all love a good graphic tee, but there's a line between expressing yourself and turning yourself into a walking advertisement.

  • The Fail: Wearing a shirt with an obnoxious logo, a band tee you don't actually listen to, or anything that’s offensive or distracting.

  • The Fix: Choose your graphics wisely. Opt for tees that reflect your interests and personality without being too loud or controversial. I really like bands t-shirts. A subtle band logo or a cool design is always a good choice. And remember, less is often more. Keep it clean, simple, and true to you.

teenager wearing a t-shirt with a very large logo

teenager wearing a t-shirt with a very large logo | Image: Supplied

The 'Comfort Over Everything... To a Fault' Catastrophe

Okay, comfort is KEY. But there’s a difference between comfy-chic and looking like you just gave up.

  • The Fail: Pajama pants (yes, people actually do this), stained sweatpants, or anything that's clearly meant for lounging at home and nothing else.

  • The Fix: Elevate your comfort. There are tons of ways to be comfortable without looking sloppy. Opt for joggers instead of sweatpants, a soft knit sweater instead of a hoodie, and clean sneakers instead of slippers. It’s all about finding that sweet spot where comfort and style meet. And remember, showing that you care about your appearance shows respect for yourself and those around you.

teenager wearing pajamas to school

teenager wearing pajamas to school | Image: Supplied

So, there you have it – five common school outfit fails and, more importantly, how to fix them! Remember, fashion is all about expressing yourself, so have fun with it! What are some of your biggest school outfit struggles? I'd love to hear about them!

“Dress like you’re already famous.” – Rachel Zoe

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