What to Wear on the First Day of School (Teacher or Student Edition)

Nobody says the first-day outfit matters, and everybody secretly agonizes over it anyway. Here’s a straightforward way to get it right without overthinking it.

For teachers: approachable, not exhausting

The first day sets the tone for the whole year, and that includes what you’re wearing. A graphic tee under a cardigan or blazer reads as put-together but still human — much better than head-to-toe “first day of school teacher outfit” perfection that you’ll never repeat by day three. A design with a little dry humor about the school year works especially well; it gives students something to smile at during the inevitable awkward first fifteen minutes.

For students: comfortable enough to actually focus

The best first-day outfit is the one you forget you’re wearing by second period. Skip anything that needs adjusting, and pick a graphic tee that says something about your actual personality rather than something you think you’re supposed to wear. A shirt with a bit of humor on it is an easy, low-effort conversation starter in a room full of people who don’t know each other yet.

The one rule that applies to everyone

Comfort first, then character. A well-made cotton tee in a design that actually makes you laugh will outperform anything trendier that you’re not going to want to wear again by October. That’s really the whole idea behind the Back to School collection — one design for the “I’m not emotionally ready for this” crowd, and one for the “new notebook, new me” crowd, both built to actually get worn.

More back-to-school ideas

If you’re shopping for someone else instead of yourself, the back-to-school gift guide has more options beyond apparel, including a few that work well for teachers specifically.