I’ve been teaching long enough to know that what you wear really matters when you're on your feet, juggling classes, playground duty, meetings, and everything in between. I made this list of comfy, practical, and still-cute pieces that I either wear ...
Sections
5
Shirts and Blouses
Pants
Accessories
Shoes
Dresses
Shirts and Blouses
Staple tops I wear (or plan to!) that are comfy, classroom-friendly, and don’t need much ironing — always a win on rushed mornings.
A go-to for those mornings when you want to look put-together but don’t have the energy to think too hard. The embroidery gives it a bit of personality, and the fit is roomy enough to stay comfy all day in the classroom.
Women's Striped Print Embroidered Button-Up Casual Long Sleeve Shirt - SHEIN Australia
Easy yes for busy teaching days — light, simple, and goes with pretty much anything. The roll-up sleeves are super practical, and it has that clean look without feeling too stiff or formal.
EMERY ROSE Women's Spring Floral Print Notch Collar Blouse
I’m eyeing this one for hot classroom days — 100% linen, so it should be breathable and light. Love the soft pink too — feels like an easy way to add some colour without going too bold.
MOTF Premium Pure Linen Button-Up Shirt
Pants
Loose, breathable, and still polished — these are the kinds of pants I look for to survive a full teaching day without feeling restricted.
Haven’t tried these yet, but they’re sitting in my cart. Love the look of the tie waist and wide leg — seems like they’d be comfy for work but still feel polished. Planning to pair them with a tucked-in shirt for school days.
Calvaya Women's High Waisted Belted Pleated Elegant Wide Leg Pants
These caught my eye for school — love that they’ve got pockets and the royal blue feels like a fun change from the usual black or beige. Thinking they’d work well with a tucked-in blouse or even a plain tee on casual days.
EMERY ROSE Solid Color Loose Wide Leg Elegant Pants With Pocket
These are in my cart — the high waist and flowy cut look super comfy for work, and the apricot colour feels like a nice switch-up from the usual neutrals. They come with a belt and pockets, which is always a win for classroom days.
Women's Belted Wide-Leg Pants
Accessories
Minimal but cute pieces that add just enough personality to an outfit without getting in the way while teaching.
This one’s sitting in my cart — love the minimalist look and the geometric design feels like it’d go with everything. Thinking it could be a nice little detail to dress up a plain work outfit without overdoing it.
Minimalist Geometric Women's Bracelet
This one’s been sitting in my cart for a while — really like the simple heart design. Feels like the kind of necklace you could wear every day, even to school, without it feeling too dressy or fussy.
Retro S925 Pure Silver Heart Pendant Necklace
This one’s on my wishlist as a little treat for myself — perfect for cooler classroom days. It looks super soft, and the wool-cashmere blend sounds like it’d actually keep you warm. The simple design makes it easy to throw over any outfit without ove...
Coach Scarf
Shoes
Shoes that can handle a whole school day — from standing, walking, and yard duty to the random sprint down the hallway. Comfort first, always.
I have an older version of these and they’ve been such a solid pick for long days on my feet. Super comfy, supportive, and they actually hold up well. If you’re on your feet a lot — teaching or running errands — this brand’s been a game-changer for m...
Sophie IV Black
These are next on my wish list — I’ve had great luck with this brand before and love that these can be worn with or without laces. The support is legit (my feet don’t ache after a full day), and they’ve got that clean white sneaker look that goes wit...
Nat III White
I own a pair of these and honestly love them — super comfy, actually waterproof, and they don’t look clunky like most rain boots. I wear them on wet school days and they hold up great. Felt like a practical little treat that also looks cute with most...
Bobbi Ankle Boot // Rust
Dresses
Easy, throw-on-and-go outfits that still look put-together. These are the kinds of dresses I’d wear on days when I want to feel a little more polished but stay comfortable.
Just found this EMERY ROSE square‑neck maxi dress on SHEIN — the clean, sleeveless cut and relaxed fit screamed easy‑to-teach‑in vibes. I love the notched neckline detail—it looks simple but feels elevated enough for school. It’s lightweight and flow...
EMERY ROSE Women's Sleeveless Square Neck Casual Summer Maxi Dress
This one’s giving comfy but still put-together — love the loose fit and the color block design adds something a bit different without being loud. Looks like it’d be great for school days where you want easy movement (and it has pockets!).
EMERY ROSE Women's Color Block Patchwork Print Loose 3/4 Sleeve Maxi Casual Dress
This one’s a bit more of a dressy pick — thinking it’d be perfect for a school event or dinner after work. Love the backless halter vibe and the flowy fit. Definitely feels like a ‘treat yourself’ kind of piece, especially with the silk.
Premium Silk Blend Belted Halterneck Dress
This one feels like the kind of dress you wear when you want to look like you’ve got it all together — without much effort. The scalloped detail and puff sleeves give it a polished vibe, and the belt helps pull it all in. Feels like a bit of a treat-...