My qualifications for a good teacher outfit include comfortable, not too short (so I don’t have to worry about bending over), and POCKETS! I wore a half apron most days to teach, but it’s always good to have some pockets just in case! Please note this post contains affiliate links.

I put together these outfits with just five core pieces from Madewell, Amazon, and Everlane. A few of these are more investment pieces (and some are now sold out, as of 2023), so keep in mind you can replicate these looks with less expensive options— I’ll be linking different options throughout.

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True, when you think “teaching” you don’t usually think “bodysuit,” but hear me out! You don’t have to worry about keeping it tucked in, and if you find one with snaps, you don’t have to worry about any trouble using the restroom! This jumper is my new favorite piece of clothing. It’s long enough you don’t have to worry about sitting or bending over, but not so long that it looks matronly. Plus, pockets!

I’m a recent convert to wide-leg pants! This cropped version is cute for spring, has pockets, and is formal enough for most school settings. The striped button up top looks cute tied, but can also be worn tucked in or out.