What Not to Wear on the First Day Back at School

Most first-day-of-school advice focuses on what to wear. The mistakes are usually more useful to know about — they’re the reason a first-day outfit that looked good in the mirror falls apart by second period.

Skip anything completely untested

Brand-new shoes that haven’t been broken in, a stiff shirt straight out of the packaging, an outfit you’ve never actually worn for a full day — day one is the wrong time to find out something doesn’t work. Wear the shoes around the house first. Wash the shirt at least once before wearing it.

Skip anything that needs constant adjusting

If it needs to be pulled up, tucked in, or fixed every ten minutes, it’s going to be a distraction all day, not just an annoyance. Comfort problems compound over a six-hour day in a way they never do trying something on for five minutes at home.

Skip going completely blank

A totally plain outfit isn’t a disaster, but it’s a quiet missed opportunity — it gives classmates or a new group of coworkers nothing to react to. Even a small graphic tee with a bit of personality, like something from the Back to School collection, gives the day’s inevitable small talk an actual starting point.

Skip dressing for who you think you’re supposed to be

Overdressing to impress or underdressing to seem unbothered both tend to feel forced by lunchtime. The first-day outfit guide covers this in more detail, but the short version is: comfort first, then something that’s actually true to how you feel about the day.

Shop the collection

Browse the full Back to School collection for a first-day option that avoids all four mistakes at once.