My Favorite Teacher Outfits from the School Year
As a teacher, I love creating outfits that are both comfortable and cute, and that help me feel confident, put-together, and ready for a day with my students. Throughout the past school year, I’ve worn a mix of fun and realistic looks that felt like “me” but were also perfect for the classroom. I rounded up a few of my absolute favorite outfits to share here. If you’re a teacher (or just love a good outfit idea), I hope this gives you some inspiration for your own wardrobe!
1. The Denim Dress Moment
A classic piece I reached for over and over-my denim dress. It’s comfy, structured just enough, and pairs easily with sneakers, clogs, or sandals. I love that I can dress it up with accessories or keep it simple on busy mornings.

2. Linen Pants + Layers
One of my comfiest combos: wide-leg linen pants and a tee (long-sleeve in this case). I love how the denim vest added a layer without bulk here, and then my rainbow necklace added a pop of color. This outfit felt playful but polished, and the breathable fabrics were perfect for those transitional weather days.

3. Floral Maxi + Light Blue Cardigan
This floral maxi skirt is one of my very favorite items in my closet! Here I paired it with a light blue cardigan that brought out the colors in the dress beautifully. It was a perfect outfit for days when I needed something easy but still felt cute.

4. Rainbow Sweater + Pixie Pants
This sweater made me feel happy everytime I wore it! It is older and sold out, but I will link some similar ones. I didn’t know how much I’d love wearing it but it became one of my favorite pieces this year! Here I just added pixie pants, and a pair of neutral mules.

5. Layered Neutrals
For a neutral look, I wore a brown long-sleeve tee layered under a white sweater vest, paired with black pixie pants and brown accessories. I can’t explain fully why I love this one, but it’s something to do with the combo of brown and black (yes, they can go together!) and the sweater layer.

6. Light Blue + White Combo
I loved this color combo! The light blue trouser pants are so cute on their own, but I loved them with a white tee and layered with an open cropped cardigan. It’s such a pretty palette and these pants are super comfy and petite friendly!

7. Tan Maxi + Cropped Denim Shirt
This was one of those unexpectedly perfect combos: a flowy tan maxi skirt, a white tee, and a cropped denim shirt layered on top. It was comfortable, easy to wear, and cute!

8. White Linen Skirt + Yellow Tee
A bright, sunny outfit that made me feel ready for spring: my white linen skirt and a cheerful yellow tee, topped with my favorite cropped denim shirt. I have worn this denim shirt so many ways and always love it!

9. Pink Pants + Denim Shirt
These pink pixie pants are the prettiest color, and I paired them with a classic denim shirt and my Birkenstocks. Easygoing, colorful, and still classroom-appropriate.

10. Denim Jumper + Crochet Cardigan
I loved how this one came together! I wore my denim jumper layered over a basic tee and topped with a crochet cardigan.

A Few More Favorites…
- First Day of School Maxi Dress: Flowy and comfy and some of my favorite colors! The perfect “hello, new school year” outfit.
- Petite-Friendly Blue Pants + White Tee: These petite friendly pants are so good. I love them with a simple white tee.
- Striped Button Down + Pixie Pants: Sometimes the simplest combos are the best. This was a no-fail, classic outfit.
- Purple Linen Pants + Denim Shirt: I loved the soft purple of these pants and they’re so cute paired with deni.
- Mountain Moverz Graphic Tee + Comfy Pants: I always love this tee! Here I paired it with petite-friendly comfy black pants and threw a purple sweater on top for some color. You can use code STEPHSHARES20 to save on the tee at Mountain Moverz!





Whether it was a colorful sweater, a perfectly fitting pair of pixie pants, or a layered combo that felt just right, these outfits were so fun to put together this school year. Let me know which one’s your favorite—or what your go-to teacher outfit is!
And if you’re looking for more outfit inspiration for midsize bodies or teacher life, follow along on Instagram or subscribe to my newsletter!

