8 Cozy Winter Teaching Outfits

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Looking cute in the wintertime is a struggle! Between the snowstorms and freezing temperatures, being warm is more important than being fashionable. But these winter teaching outfits work for looking cute and staying warm!

Where teachers shop for clothes

These winter teaching outfits are made with budget-friendly staples and higher-end pieces. I love finding basics at Target, J.Crew Factory, Madewell, and Old Navy.

How do I afford more expensive options? Short answer, I rent them! Renting clothing is so easy and works perfectly for those of us who love to buy new clothes every time we walk into Target.

8 outfits for winter — These 8 cozy winter teaching outfits are the inspiration for putting together your own wardrobe. I love mixing basics with fun trendy pieces to keep my outfits looking interesting.

I rent clothing with a company called Nuuly which I have raved about in past teaching outfit inspiration posts. Simply put, I get to rent 6 pieces of clothing for a month, send them back and get to pick out 6 new items. It’s easy to pick and choose from whatever types of clothing you want. The reviews help you get the sizing right so that your clothes will fit! It’s like online shopping meets dressing room but all from the comforts of your own apartment. I’ve been using them for almost 2 years now and I’m still in love!

Want to check out Nuuly for yourself? Use this link to get a discount on your first box!

Now onto the winter teaching outfits!

Looking for cute spring outfits for teachers? This post has you covered!

Want women summer work outfits? Check out this blog post for inspiration and tips!

Summer to Fall for fashion outfits are linked here.

Winter outfits with skirts

Fun fact, I actually wear more skirts in the wintertime! I think it’s because boots tuck in nicely and fleece-lined tights are actually warmer than jeans. I picked up these fleece-lined tights from Amazon that are perfect for colder weather and look sheer! Perfect for wearing winter outfits with skirts.

Winter teacher outfit #1

how to wear a patterned skirt — This patterned skirt was a fun find. I love the deep green color and this is a pattern I would never own but it was fun to rent!

Black Bodysuit: Madewell

Skirt: rented with Nuuly

Boots: Dr Martens

Teacher winter outfit #2

chunky cardigan outfit — This chunky cardigan takes center stage in this outfit. Probably one of my favorite winter teaching outfits!

Chunky Cardigan: rented with Nuuly

Black Tank: Old Navy

Black Skirt: Poshmark

Boots: Dr Martens

Teacher winter outfits #3

winter outfits with skirts — Plaid is such a wintertime classic and this one with the buttons is so cute! The rest of the outfit is pretty simple to let the skirt shine!

Black Sweater: Alter’d State, similar

Plaid Skirt: Madewell

Boots: Dr Martens

Winter outfits with leggings

Who doesn’t love wearing leggings? These winter outfits with leggings are sure to keep you warm and looking stylish. These leggings are the BEST I have ever found and that includes those pricey ones from that one store. Quality is top-notch and bonus points for side pockets!

Purple Sweater: rented with Nuuly

Leggings: Amazon

Boots: Dr Martens

Comfy teacher clothes

Hear me out, these plaid pants are essentially leggings! They look cute and actually are dress pants but are the perfect comfy teacher clothes.

how to wear plaid pants — Dress pants are a teaching basic but they don’t have to be boring. This pattern pair is fun while still being warm.

Sweater: rented with Nuuly

Plaid Pants: rented with Nuuly

Boots: Dr Martens

Teachers winter outfits

This winter teaching outfit is great for a casual Friday. My straight-leg jeans are actually from the thrift store but I rented a pair just like them a few months back. Might I be a straight-legged jean convert?

outfits with straight leg jeans — This turtleneck bodysuit and straight-leg jeans remind me of the 90s and I’m totally here for it! Slip on a pair of high tops and get to class!

Black Turtleneck: Madewell

Jeans: Thrifted

High Tops: Converse

Plaid Headband: J Crew

Winter outfits for teachers

Traded my straight-leg jeans back for skinny in this winter outfit. This two-toned sweater is a fun find and looks great with black jeans too!

winter teaching outfits for Friday — This Walmart sweater looks stylish with jeans and Dr. Martens. Perfect for a casual Friday.

Sweater: Walmart

Skinny Jeans: Madewell

Boots: Dr. Martens

Teacher outfits ideas

Last but not least, black jeans! These are my number one staple for winter teaching outfits as they pair with any sweater and look pulled together without much thought.

sweater and black jeans outfit — A simple sweater and black jeans combo get a leg up with combat boots.

Sweater: Madewell

Black Jeans: Everlane

Boots: Dr Martens

More winter teaching outfits

Looking for even more inspiration for winter teaching outfits? I’ve found a bunch of options on my Pinterest board for easy pinning. If you want to search for blogs and videos then I’ve linked a few below!

Which winter teacher outfits are your favorite? Let me know in the comments!

Where teachers shop for clothes