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

They’re almost better than jeans!

Collage of women wearing casual dresses with pockets

It’s time to revamp your teacher wardrobe! And, of course, comfort is key. Since we can’t wear our preferred T-shirt and shorts (aka, the spring and 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! Choose 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 cooler weather, 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, no matter the time of year. This dress solves the comfort problems you may face if your room can feel like the frozen section at the grocery store. (Psst: We also recommend layering up with a shacket!)

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 swing dress can be dressed up or down

Black sleeveless t-shirt dress

This classic black dress can easily be dressed up or down with a scarf or bold jewelry. It’s perfect for adding your favorite colorful shoes or teacher bag!

Buy it: Sleeveless Vintage Mini T-Shirt Swing Dress/Old Navy

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 choose from.

Buy it: Navy Floral Dress/Amazon

8. Tie-dye isn’t just for kids!

Dark tie dyed casual 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.  Ruffles are too cute

Orange puffy sleeve casual maxi dress

The puffy sleeves and ruffle hems are too fashionable to resist!

Buy it: Women’s Puff Short Sleeve Ruffle Collar Dress/Target

10. Prance around your classroom with this fun geometric pattern

Short sleeve dress with geometric pattern

Extra points if you wear this to teach geometry lessons!

Buy it: ZANZEA Bohemian Geometric Printed A-Line Dress/Walmart

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.  Denim is always in style

Gray denim dress with tie and pockets

A sneaky twist on regular jeans! Plus, the material is lightweight and comfy, ready for hours of wear.

Buy it: Women’s Long Sleeve Button-Down Denim 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. Choose from multiple color options or long-sleeves for cooler days!

Buy it: Lace Detail T-Shirt Dress/Amazon

14. Be teacher-ready in a smock dress

Black short sleeve flutter dress with pockets

This smocked-look is teacher ready! Your co-workers will be asking where you purchased this one.

Buy it: Women’s Flutter Short Sleeve Shift Dress/Target

15. Channel your inner hippie

Blue embroidered casual dress for teachers

Add a belt, some cute earrings, and a pair of comfy sandals, and you’ve got an outfit even your students will compliment.

Buy it: Women’s Long Sleeve Embroidered Dress/Target

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 rosy hues

Pink sleeveless casual dress with pockets

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

Buy it: Women’s Sleeveless Knit Ballet Dress/Target

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 choose from! Our faves? Leafy ferns, snakeskin, or tie-dye!

Buy it: Green Fern Dress/Amazon

21. You can never have too many florals

Short sleeve floral casual dress

Especially when the blooms are as colorful as this delightful midi-dress pattern!

Buy it: Floral-Print All-Day Midi Swing Dress/Old Navy

22. Add some chic utility-style to your wardrobe

Green utility dress with pockets

The cinched waist on this all-cotton design is flattering on everyone. It also comes in a fun striped earth-tone option.

Buy it: Free Assembly Women’s Femme Utility Dress/Walmart

23. Say hello to lovely subtle details

Light blue teacher dress with pockets

The lattice embellishments and tortoise shell buttons are too sweet on this dress!

Buy it: Women’s Short Sleeve Lattice Detail Dress/Target

24. Embrace bold sleeves

Black dress with bell sleeves

As if those gorgeous sleeves weren’t enough, the pockets seal the deal for this boho look.

Buy it: Free Assembly Women’s Shift Dress with Bell Sleeves/Walmart

25. Did we mention we love a good flower pattern?

Black floral casual dress

This darker take on the classic floral design can go from the classroom to date night!

Buy it: Puff-Sleeve Smocked Floral-Print Mini Swing Dress/Old Navy

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

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