Time for Back-to-School shopping, which means new outfits for students *and* teachers. Whether you're in the classroom, at a parent-teacher meeting, or running an after-school activity, you need teacher-friendly clothing that balances comfort and professionalism.

That cozy versatility is what Dudley Stephens is made for. Our pieces are made from recycled fleece and stretchy performance fabrics that stand up to demanding classroom days. They’re made to wear over and over for seasons to come, bringing your cost-per-wear into pennies territory—plus, we offer a 15% sitewide discount for teachers, all of which is the kind of math we can really get behind. 

Here are a few teacher wardrobe essentials to help you stay stylish, comfortable and ready for anything the school day throws your way.

Cobble Hill Turtleneck in Black

Our #1 bestseller since our brand’s launch for a reason. Classic, timeless & wearable with everything, it’s the perfect essential for a busy teacher’s wardrobe.

Brighton Boatneck—any shade

An instantly iconic neckline (hello, Audrey Hepburn fans) in lightweight Terry, ideal for those still-warm September days as the year gets underway.

Brighton Boatneck in Nantucket Fog

Brentwood Maxi Dress

Dressing for school days doesn’t get any easier than a shirt dress—especially one you can toss in the washing machine & wear again, wrinkle-free.

Brentwood Maxi Dress in Blue Pinstripe

A Little Black Pant

Ever wish you could just wear your workout leggings to work, for maximum comfort? Our pants are even better—the feel of your favorite gym-ready pant, with work-ready styling.

Palm Bay Pant in Black, St. Simons Pant in Black

Beaufort Button Down

A quintessential striped button down shirt, with the ease—and easy care instructions—of a Dudley.

Beaufort Button Down in Blue Pinstripe

 

Wellington Blazer

Top off your look with a blazer that reads “top-notch teacher” but feels more like “favorite Sunday sweatshirt.”

Wellington Blazer in Navy

 

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