Looking to change up your wardrobe this school year? Here’s just the thing. Check out all the fashionable and comfortable outfits that one of our teacher writers put together for the 2023-2024 school year. These cute teacher outfits will have you feeling ready to rock the day! Pick out your favorite, and treat yourself to a new addition to your closet (because you deserve it).
(Note: WeAreTeachers may collect a small portion of the profit from links within this article. We only showcase items we love!)
Skirt, Shirt, and Shacket
Brooke Naumoff
This look is a great blend of dressy and casual. The skirt is comfortable, sandals are always a win, and the shacket for those freezing cold classrooms.
Buy it: White Flutter Sleeve Shirt at Dry Goods, Pink Knit Shacket at Dry Goods, Pink Skirt (similar) at Amazon
Ruffle Dress
I love this dress! I purchased it for the first day of school. Anyone else (sometimes) treat themselves to a first-day of school outfit? This dress is the comfiest material. If you’re comfortable in a wedge, the ones linked below are cute, but I also think it would pair well with a flat or sandal. Because unless it’s test day, it’s sandal/flat day.
Buy it: Ruffle Dress, Wedges , Sandals
Jeans, T-Shirt, and Cardigan
This look is a Walmart find! I love the fit of the jeans and they were very comfortable. The cardigan is a staple in every teacher’s wardrobe. This outfit is perfect for casual Friday.
Buy it: Striped Shirt, Wide-Legged Jeans, Maroon Cardigan
Wide Legged Dress Pants and Silk Top
If you’re at a school that has a fancier dress code, this look is for you! It could also be a great ensemble for a teacher interview. You could even sub in flats for heels if you’re looking to dress it down.
Buy it: Black Silk Top , Cream Dress Pants, Kitten Heels (Truly comfortable for work!)
Colorful Pants and Checkered Sweater Vest
Ride the Barbie wave! There are pops of pink in several of these outfits because it seems everywhere you go, Barbie has invaded! I don’t mind it at all. I love brighter colors especially when the weather feels dull. It makes me feel like I am combatting the gloom with my outfits.
Buy it: Pink Wide-Legged Pants , Sweater Vest
Ankle Cargo Pants and Flowy Top
This outfit was so comfortable! This is head to toe Old Navy! The cargo pants can be cinched at the ankle and the flowy top was a perfect balance. Add those mules to the cart!
Buy it: Cargo Ankle Pants , Flowy Top, Woven Mules at Old Navy
Denim Dress
I’ve been on the hunt for a good denim dress for a while now. I found this at Express and wasn’t sure how I’d like it but I love it! It is a heavier denim material and I think the sleeves are so fun!
Buy it: Denim Dress , Amazon Denim Dress Option
Black Dress Pants and Striped Dress Shirt
I love the classic black and white combination. Both the top and pants can be mixed and matched into countless combinations. Swap out sandals for a pair of closed toe shoes, and this is another great outfit option for a teacher interview.
Buy it: Black Dress Pants , Black and White Striped Shirt, Amazon Striped Shirt
Printed Pants and Shacket
Step outside of your comfort zone and try a bold pant! If you’re shorter (like me), you may need them hemmed or wear with a boot.
Buy it: Floral Pants, Shacket, Rhinestone Sandals
Maxi Dress
The puffy sleeves, the ruffles, the length of this dress may make you want to glide through the rows of desks like you’re in a beautiful garden collecting flowers in your basket.
Buy it: Puffy Sleeve Maxi Dress
Barbie-Core Pants and White Top
Pixie pants are a constant teacher favorite! They come in many prints and colors. Pair with a simple top or sweater and you’re all set.
Buy it: Pink Dress Pants, White Shirt
Comfy Dress
I think the reason why I choose dresses so much during the weather appropriate months is just because they are the easiest option. I have to think about just one piece and I’m all set. This one is like wearing a t-shirt, a big long bed-time t-shirt.
Buy it: Short Sleeved Tiered Knit Dress
Pencil Skirt and Silk Top
This is another great outfit for a teacher interview. If your dress code leans more polished and sophisticated, this pencil skirt and peplum shirt is a cute combination.
Buy it: Black Pencil Skirt, Silk Shirt, Amazon Skirt
Pink Silky Pants and Smiley Face Shirt
If you want to wear pants that feel like pajama pants, these are the winners. I could not find the exact pair to link from Altar’d State but I linked a similar option from Amazon. Pair with your favorite teacher t-shirt.
Buy it: Pink Silky Pants, Smiley Face Shirt
Ruffle Skirt and Ruffle Shirt
If you like the look of a skirt but want one that is less constricting than a pencil skirt, this high-low option is very comfortable.
Buy it: Ruffle Skirt, Ruffle Shirt
Orange Sweatshirt and Jeans
For those casual Fridays at work, add this oversized sweatshirt to your closet. It comes in several colors and was a great fit. Add a new pair of jeans to your cart to put into your denim rotation.
Buy it: Orange Sweatshirt, Skinny Jeans
Floral Dress
This dress is so pretty! I like the muted color scheme and think the sleeves would allow a cardigan over this dress, if need be. They are not too puffy! The ruffle detail on the bottom is so cute!
Buy it: Floral Dress
Black Dress Pants and Cream Top
I think this look works for all seasons. Everyone needs a good pair of black dress pants!
Buy it: Black Dress Pants and Cream Top and Cream Heels
Cargo Pants and Denim Shirt
I love this outfit! This is from Walmart. The denim shirt is so soft and comfortable, as were the cargo pants.
Buy it: Cargo Pants, Denim Shirt
Floral Dress and Mules
This is an Old Navy look. The dress is almost giving Miss Honey vibes! I love the color and print.
Buy it: Floral Dress, Mules
Wide-Legged Pants, T-Shirt, and Cardigan
Everyone loves comfy pants! This look is comfy and cute. The pants are very stretchy and truly feel like pajamas.
Buy it: Linen Blend Pants, Redwoods Shirt, Cardigan
Linen Dress
I like the length of this dress. I think it would go best with boots for the fall and winter. The dress pictured is from Macy’s but I could not find it on their website.
Buy it: Similar Dress
Smocked Ruffle Floral Dress
This dress is so cute on its own but could also work with boots and a cardigan.
Buy it: Smocked Ruffle Dress
Plaid Dress and Mules
I love the yellow plaid on this dress! It has a classic, Americana feel to it. Especially paired with those mules.
Buy it: Plaid Dress, Mules
Puff Sleeved Dress
You can’t go wrong with a maxi-dress like this. This option could also be good for teachers who are expecting.
Buy it: Puff Sleeved Dress
Fun Top and Dress Pants
I have these dress pants from Target in several colors. They are some of my favorites. I love how sometimes a fun sleeve is all it takes to make a statement.
Buy it: Flutter Sleeve Top, Dress Pants, Sandals
Printed Pants and Mules
Here are those same dress pants again from Target in a different print. Stock up! I think the shades of cream are so pretty. Target also carries many different options for mules which would work great at the start of the year.
Buy it: Dress Pants, Mules
