25 Teacher Workwear Outfits

Today’s post is for all my teacher friends! To help you kickstart the new school year in style, I’m sharing 25 teacher workwear outfits. I love investing in work staples that I can pair with a variety of pieces in my wardrobe! In this post, I’m showing you how to take one piece and style it multiple ways. Whether you’re doing parent-teacher conferences, teaching in person, or participating in faculty meetings, these outfits will have you covered!

SHOP TEACHER WORKWEAR STAPLES

PRINTED MIDI SKIRT

SKIRT | TOP (left) | BLAZER | BAG (left) | SHOES | TOP (right) | BAG (right)

This printed midi skirt is a must-have for your work wardrobe! I recommend pairing it with pointed-toe heels and a white top for a business casual look. For a business professional look, opt for a ribbed top and white blazer. Layer a thin belt over the top of the skirt to complete the look!

SKIRT | TOP (left) | SHOES (left) | BAG (left) | SHOES (right) | TOP (right) | CARDIGAN | BAG (right)

Another way to style this slip skirt is to pair it with a denim top! Pair it with flats for a casual Friday outfit that is comfortable and stylish.

LITTLE BLACK DRESS

DRESS | BAG | SHOES
If you’re on the hunt for a workwear piece that can easily transition from summer to fall, I’ve got you covered! This v-neck black shift dress is a timeless piece that will not only carry through the seasons but for years to come. I’ve styled it here with these gorgeous sling-back flats and my go-to tote bag by Tory Burch.

DRESS | BAG (left) | FLATS | BLAZER | JEAN JACKET | SNEAKERS | BAG (right)
Layer a jean jacket or blazer over the top of this little black dress to easily transition it into fall. The look on the left is perfect for your work week while the look on the right will have you weekend ready!

DRESS | SWEATER | BAG (left) | SHOES (left) | BLAZER | SHOES (right) | BAG (right)
Another way to style this dress is to layer a sweater over the top to create an illusion of a skirt. I love this camel bow detail sweater from J. Crew Factory. It’s the perfect neutral statement piece for fall!

CROPPED FLARE PANTS

TOP | BLAZER | PANTS | BAG | SHOES
These cropped flare pants from Target are a perfect addition to your work wardrobe! They are only $29 and come in white, black, and pink. I recommend sizing up one from your normal size.

TOP (left) | SWEATER | PANTS | BAG | SHOES (left) | TOP (right) | SHOES (right)

These brown flare pants are giving me all the fall vibes! Layer a sweater over a denim top and add a pair of statement flats, or style them with a printed blouse and heels. Whether you’re teaching in a business casual or business professional setting, these pants will be your new go-to.

TOP | JEAN JACKET | PANTS | BAG | SHOES
I love the way the brown looks against this striped tank top. Layer a denim jacket over the top for a perfect casual Friday outfit that can easily go from desk to date night!

STRIPED MIDI SKIRT

SKIRT | TOP (right) | BAG (right) | SHOES | TOP (left) | BLAZER | BAG (right)

This midi skirt is the perfect blend of style and comfort! It features an elastic waistband, modest side slit, and stretchy cotton material. These looks are perfect for parent-teacher conferences or an important meeting!

SKIRT | TOP | BAG (left) | SHOES (left) | SWEATER | SHOES (right) | BAG (right)

If you’re looking for a casual way to style this skirt, swap the heels for flats and pair it with a neutral cardigan. This button-front cardigan from Old Navy can be worn on its own or you can use it as a layer if your classroom is chilly!

BLACK FLARE JEANS

TOP | PANTS | BAG | SHOES

These cropped flare pants are a work wardrobe must-have! They are my most worn pair of black pants. I love that you can style them casually with a button-down and mules.

TOP (right) | PANTS | BAG (right) | SHOES (right) | TOP (left) | BAG (left) | SHOES (left)
These two workwear looks are a perfect example of how you can wear these cropped flare pants now and into fall. Simply swap a lightweight sleeveless shirt for a cozy sweater and you’re ready for fall!

BLAZER | TOP | PANTS | BAG | SHOES

This striped blazer is a fun addition to your work wardrobe. The neutral color allows you to pair it with multiple pieces. I’ve styled it here with a classic white tank and neutral heels.

BLACK PENCIL SKIRT

SKIRT | TOP (right) | BAG | SHOES (left) | TOP (left) | CARDIGAN | SHOES (right)

A black pencil skirt is another must-have work wardrobe staple! The fit of this one from Banana Republic Factory is excellent. I love that it’s fully lined, and it has an invisible zipper in the back.

SKIRT | TOP (right) | BAG (right) | SHOES (left) | TOP (left) | BAG (left) | SHOES (right)

If you’re looking for another way to style this classic pencil skirt, I recommend pairing it with a sweater or printed blouse. Both of these options are perfect for a business professional look. Opt for neutral heels and a black tote bag to complete the look!

Which of these 25 teacher workwear outfits are your favorite? Let me know in the comments below!