Now that I am officially back to work, I wanted to share five easy casual outfits featuring some of my favorite wardrobe staples that are great for a teacher’s assistant. Since I work in a classroom with little ones, I spend most of my time on my feet, at a desk or on the floor getting up or down, so comfortable yet pulled together outfits is a must! Think jumpsuits, graphic tees, dresses and pieces that are easy to wear. But, even if you don’t work in a classroom, these looks are perfect for a day out and about, hanging out with friends, or even for casual Fridays in the office.
Let’s kick things off with a…
As a teacher’s assistant, I love dresses that are easy to wear. In my opinion, it doesn’t get any easier than with a maxi dress and this one from Amazon is my favorite. That’s because, it’s no fuss, comfortable, has a super soft texture, and doesn’t restrict my movement which makes getting around the classroom a breeze. More importantly, this dress has pockets and that alone gets two thumbs up from me! #practical For an effortless workwear outfit, I paired it with brown sandals and added my Coach Willow crossbody bag to pull everything together.

I have yet to meet a stripe I didn’t like! There’s just something about this classic pattern that works no matter the season and this little cutie from Shein is one that I wear on repeat. The colorful stripes make it easy to mix and match with other items in my closet, but I also love that it makes my outfit playful. #kidfriendly The look I am wearing here is perfect for recess duty – I just added my favorite sandals, bum bag, and a ball cap to finish off the outfit.

Another easy outfit idea that is ideal for a teacher’s assistant is a denim dress. It’s a wardrobe staple that can be worn year after year. But more than that, it works well in the classroom because it’s casual and easygoing. So, whether I am sitting at a meeting all day or on my feet helping a classroom full of kids, throwing on a dress like this is so effortless. For an added visual interest, I slipped on a pair of leopard sneakers, and added my Old Trends top handle bag to bookend the look. I love how it beautifully ties the whole outfit together.

When I want something a little different from dresses, a black jumpsuit is an easy alternative and the reason for that is a black jumpsuit is a great way for looking put together with minimal effort. So, when I don’t know what to wear, an all-black outfit always saves the day. I literally just add shoes. In this case, a pair of studded buckle sling backs to keep things polished. Voila, instant classroom-worthy ensemble!

Naturally, we can’t talk about easy casual teacher’s assistant outfits without mentioning graphic tees. What I love the most about a graphic tee is the way they make a basic outfit way more interesting and instantly add personality. For a casual fun Friday look, I front tucked my tee with a pair of high waisted skinny jeans, tossed on a pair of white sneakers and added my large Longchamp tote bag for an extra dose of color! Such a basic look, but one that never fails.
And that’s a wrap!
What’s your go-to outfit for work?
*Disclosure: This post contains affiliate links. If you click through and make a purchase, I may receive a commission (at no additional cost to you).
**Additionally, some items linked above are not the exact item shown because it is either old or sold out, but I linked similar items for those that are unavailable.
Amber | 4th Oct 25
I love all of these outfits, Maureen, but your striped overalls are the cutest!
I hope you are having a great week so far!
Amber
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Kellyann Rohr | 21st Sep 25
You look great! Stylish and comfortable for your role as a teacher’s assistant! So glad you linked up with us!
xo,
Kellyann
Kathrine Eldridge | 18th Sep 25
I adore every single look! But that yellow and denim dresses are my fave. You are the chicest teacher!
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Nikki Wayne | 17th Sep 25
Maxi dress and jumpsuit dress for me is a very essential in your wardrobe as it is easy to use and very casual. It can be wore in any kind of occasion you will attend to.
Sonia Seivwright | 17th Sep 25
Okay, I’m obsessed — these outfits are giving comfy and confident, which is exactly what you want as a TA. Love how you mixed in classic pieces with fun little details (those sneakers are such a smart touch). Totally bookmarking this for days when I need to look cute but still move around like a ninja!
Clarice | 17th Sep 25
I think you can never go wrong with a black jumpsuit. I agree with you that it is easy to style and it is very versatile. Indeed, it is a classroom-worthy ensemble!
Barbie R | 16th Sep 25
I love the jumper idea!!! It’s such a cute and versatile option for teachers. You really showed how combining comfortable fabrics with professional touches can make classroom outfits both practical and stylish.
jerry godinho | 16th Sep 25
Love these practical yet stylish outfit ideas for teachers’ assistants—perfect for balancing comfort and professionalism in the classroom.
Melanie E | 16th Sep 25
These are all great options for teaching assistant outfits. I love that they are all very different but also all very comfortable and that layers can be to change the look and for cooler days. My favourite has to be the blue and the yellow dresses, they look lovely on you x
Catalina | 16th Sep 25
The denim dress with leopard sneakers is so fun. I also love a crossbody for hands-free days. Simple, comfy, and still put together!
mireille | 16th Sep 25
These outfits are super cute and perfect for the classroom or for an everyday mom look! I love the variety you shared. The maxi and the black suit are my favorites but I really like the other ones too. I agree about graphic tees! It just makes jeans look more interesting right away!
http://www.chezmireillefashiontravelmom.com
Stephanie | 15th Sep 25
The only thing I don’t ever wear when I am working at a school is a dress. I know a lot of teachers who do, but I am not comfortable sitting on the floor with students in a dress, and I have had to go after runners. Otherwise, I love the rest of these outfits!
LisaLisa | 15th Sep 25
All of these outfits are so cute, but my favorite is the stripe overalls…..so cute! Great outfits for a teacher’s assistant.
Beth | 15th Sep 25
I love these looks. You have such a great way of combining sass, comfort, and a suitable workplace vibe. I’d wear all of these!