Winter Teaching Outfits that Rock!

If you haven’t seen the Northeast on the news, we’re just getting through what the Weather Channel is calling an Arctic Vortex. Are you kidding me? Meanwhile, it’s supposed to be 50 degrees this coming Saturday. Guess I’ll open some windows and let the fresh air in? New England boasts some pretty wacky and unpredictable weather, but regardless, I’ll still have to get my classroom and look professional while doing it. Unless, of course, there’s a snow day! :) Dressing for sub-zero temps can be annoying and often bulky. I don’t do bulky. So without further ado, three tried (by me!) and trusted winter teaching outfits that keep you toasty without sacrificing your personal style. Cheers!

Teacher 1 Winter

I am an advocate for the sweater dress and leggings. How to make them school appropriate? Make them a Chino style legging. I have a great pair of eggplant Chino leggings by Hue that I adore. Chino leggings are thicker, warmer, and none of this is bulky. Pair with some black booties (I got mine at Target) and some simple bangles and earrings.

teacher winter 2

I’m obsessed with blazers because they can make anything look polished. I spoke about blazers in my last teacher outfit blog, but this time we’re focusing on corduroy blazers that will keep the heat in and the bulk out. Layer your blazer with a simple turtle neck sweater like the one above and pair with sleek dress pants and simple heels. Add a chunky bracelet (I love this one with the Eiffel Tower).

winter stuff


Stubborn? Want to wear cutesy clothes and not worry about layering or strategic planning? That’s fine. I have days like that, too. Here is my arsenal of winter fashion that looks amazing for the school, the nice restaurant, or just for wearing around your home when the heat is set too low. I bought a long peacoat like this years ago and I bring it out only for sub zero temps. Though it was pricey, it’s worth every penny. I also have mittens similar to these Kate Spades (mine are a budget friendly Hi and By set from Old Navy) and an infinity scarf from Old Navy as well. My Clarks boots (I love, love, love, Clarks) keep my feet warm and toasty since Uggs really don’t jive well in the classroom.

Though I don’t have a “set in stone” dress code where I teach, many of teachers do! However, as I learned way back when while working in a school with teacher dress code, style doesn’t have to be sacrificed if you know where to place your style and how to weave it in. Stay toasty, my friends.

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10 thoughts on “Winter Teaching Outfits that Rock!

  1. I really like the last two outfits! I’m not a teacher, but I can absolutely agree, a blazer goes a long way. Definitely makes your outfits more polished & turns up the fancy meter! Loveeee peacoats, except I never have an excuse to wear them. Southern California’s temperatures are never cold enough, lucky us. Hopefully you’ll get through this arctic vortex without losing any appendages due to frostbite. Stay toasty!

  2. I’m not a teacher and I don’t wear women’s clothing, however wouldn’t the high heels cause pain after a while, after all you’re up, your down, in and out of the classroom, etc. For some reason I imagine high heels for teachers to be more uncomfortable than for any other profession.

  3. Oh my goodness I love your style so much. There is just something so incredibly satisfying about picking out “teacher clothes.” One place I seriously fail with is shoes. I tend to get one pair of black boots until they wear out and hope they go with every outfit. It never works. I am always sad. Those silver ones are adorable.

  4. These look really great. I think you make a really valid point, in that you can still look professional and have some style as well. I guess it depends on you as a person and how you feel about it.

    I really love the styles you have picked out, I am sure they look so great. Especially in the cooooooold!

  5. I love them! I’m a huge fan of leggings and sweater dresses, so the first outfit is definitely up my alley. I love the outfit with the blazer too. It can make even a casual outfit come together.

    I hope the weather is warming up for you at least a little bit.

  6. I love bundling up during the winter too but now that I walk so much (across downtown before and after work)… no matter how cold it is, I ALWAYS heat up!! But when I don’t dress warm enough, I regret it. I have this problem where I naturally walk super fast but I can’t help it. Sigh. I think fall is my favorite season because you can still wear thick sweaters but don’t need to bulky winter jacket.

  7. The first and third outfits are the ones I can definitely see myself wearing. It’s really weird to read about winter outfits because it’s Summer in Australia (where I live) and it has been extremely hot.

  8. They all look great, but especially the second one! I love blazers, they’re a great way to pull an outfit together, but if they keep you warm, even better! The bracelet on the second outfit is lovely, very interesting, it’s not often you see a bracelet like that!

  9. I really need to go shopping. I have like… 3 tops and 2 bottoms that I just rotate around every week and… It gets really old. But I really just don’t have any nice clothing to go to school in. 8( Those look so comfy and warm…

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