It’s time to revamp your teacher wardrobe! And, of course, comfort is key. Since we cannot wear our preferred T-shirt and shorts (aka, the summer uniform) to work, we’ve rounded up some dresses that are a close second. These super comfy and casual dresses for teachers are awesome. Plus, they have pockets! Chose your favorite to get compliments galore from fellow teachers. 

(Just a heads up, WeAreTeachers may collect a share of sales from the links on this page. We only recommend items our team loves!)

1. We love polka dots!

Black and white polka dot dress with pockets

Who wants to feel like they are in a soft T-shirt all day but also hide snacks in their pockets and channel Julia Roberts at the same time? This option is so flowy, and it comes in over 40 pattern options! You’re sure to find a favorite.

Buy it: Polka Dot Dress/Amazon

2. When a dress feels like pajamas, you buy it.

Grey v-neck maxi dress

Here are so many perks about this dress: The length makes it perfect for late summer and early fall and pockets bring joy to any Monday. Imagine wrapping yourself up in jersey sheets, throwing on some gladiator sandals, and calling it a day. You can bring that vision to life with this dress.

Buy it: V-Neck Split Hem Dress/Amazon

3. If your classroom is freezing, long sleeves are the way to go.

Long sleeve Winter dress

If your classroom is like most, you have to layer up, even at the start of the year. This dress solves the comfort problems you may face if your room can feel like the frozen section at the grocery store.

Buy it: Long Sleeve T-Shirt Dress/Amazon

4. A good vintage flair is hard to resist.

Vintage navy dress with florals

This could be a casual, a happy hour, or even a party dress. It has a puffy skirt, and there are many great designs to choose from.

Buy it: Vintage Flair Dress/Amazon

5. This flair dress can be dressed up or down.

Pocketed flair dress

This versatile pattern can easily be dressed up or down with a scarf or bold jewelry. Muted tones are perfect for adding your favorite colorful shoes or teacher bag!

Buy it: Pocketed Flair Dress/Target

6. These stripes are chic.

Chic black and white striped dress

This dress will look like you tried hard to look good. It’s definitely the kind of dress that will bring on some compliments. Check out navy, green, and bright colored options too!

Buy it: Chic Striped Dress/Amazon

7. Floral is always in.

Navy floral pocket dress

Want to look like you’re ready to head to the Kentucky Derby or high tea but also be comfortable and have a hiding spot for snacks? Then you need this dress. There are many floral options for you to chose from.

Buy it: Navy Floral Dress/Amazon

8. Tie-dye isn’t just for kids!

Burnt orange tie-dye dress

Show your students how cool you are with this fun swing dress. It comes in different tie-dye colors and a plain T-shirt dress option too.

Buy it: Tie-Dye Dress/Amazon

9. Ruffle hems are too cute.

Ruffle hem sleeveless dress in tan

Try this dress in tan, coral, or mint. The ruffle hem and waist tie are too fashionable to resist!

Buy it: Ruffle Hem Dress/Target

10. Prance around your classroom with this fun maxi.

dotted maxi dress in burgundy

This maxi is flowy and classroom ready! We love this dotted detail. 

Buy it: Dotted Maxi Dress/Target

11. Basics are a must.

Casual dresses for teachers - swing dresses

This dress comes in so many great solid colors. This dress is also perfect to wear with a pair of fun leggings, a statement necklace, or bright shoes. (Need some leggings ideas? We have some for you!) We even asked some teachers we know to test it out, and they loved it (check out the photos below)!

Teacher dress

Buy it: Tunic Pocket Dress/Amazon

12. Midi-dresses are in style.

Ruffle tank dress in grey

These ruffle sleeves are everything! Plus, the material is lightweight and comfy, ready for hours of wear.

Buy it: Ruffle Tank Dress/Target

13. We’re loving this lace detail.

Lace t-shirt dress in red wine color

This dress is one that is unique in its design with adorable lace. Many color option and long-sleeves for cooler days are ready for your to choose from.

Buy it: Lace Detail T-Shirt Dress/Amazon

14. Be teacher-ready in a smock dress.

Orange striped smocked dress

This smocked-look is teacher ready! We’re also loving the other option in this style with a blue floral pattern. Your fellow teachers will be asking where you purchased this one.

Buy it: Orange Smocked Dress/Target

15. Because some of us are excited about boot season …

Casual Dresses for Teachers - Boots

A v-neck and long sleeves give this swing dress a different variation. Plus, this dress goes perfectly with classic brown boots during the fall. In teacher fashion, throw on a scarf with a cute jacket, and you’ve got an outfit your coworkers will compliment.

Buy it: V-Neck Long Sleeve Swing Dress/Amazon

16. Everyone needs a maxi dress in their life.

Boho style black and white patterned maxi dress

This boho style is great for the start of the school year. This dress is a true mix of being a maxi and still being casual. Choose from over 40 variations, including florals, animal prints, and solids.

Buy it: Boho Maxi Dress/Amazon

17. This is a teacher go-to.

Striped dress with waist tie

This Amazon bestseller is hard to beat. Pick your favorite color stripes, and you’re ready to rock this day in this super comfy dress.

Buy it: Waist Tie Striped Dress/Amazon

18. Bring out the cheetah.

Cheetah cami dress

Toss on your favorite colored cardigan, and your outfit is ready to go!

Buy it: Cheetah Cami Dress/Old Navy

19. Time for some color in your closet.

Colorful Halter dress

Grab this super colorful option or opt for a more muted, solid tone if you love this dress’s style.

Buy it: Colorful Striped Dress/Amazon

20. Patterns make outfits fun.

Green fern short sleeve dress

So many patterns to chose from! Our faves? Leafy ferns, snakeskin or tie-dye!

Buy it: Green Fern Dress/Amazon

Did we miss any of your favorite casual dresses for teachers? Come and share in our WeAreTeachers Chat group on Facebook.

Plus, check out our dresses that will make you feel like Ms. Frizzle.

20 of the Best Casual Dresses (With Pockets!) for Teachers