Winter teaching outfit favorites

As the weather gets colder dressing for teaching is a challenge. Why is it that we put college classes in different buildings than professor offices?! What do you wear when it’s freezing outside but your classroom is heated by an overactive, ancient radiator? I don’t have all the answers, but I do have a few favorite items I reach for over and over as it gets cold. Here is what to wear as a tenure track professor or teacher for fall and winter!

A short sleeve sweater

Ok short sleeve sweaters are my favorite thing, surprisingly. They look professional under blazers, they’re soft and comfy, and they provide the perfect amount of coverage that I prefer in a classroom. I wish I had one when I was on the job market, I would have worn it under every interview suit.



Bag is sold out (but here if you want to find it on Poshmark/Ebay!)


A plaid blazer

Plaid and elbow pads are basically professor style 101. I really prefer a soft, less structured blazer so that it’s easy to move around while teaching, and I have found H&M to be a reliable producer of such blazers (I have thrifted three). I would also like to say the 1-2 smart pairs of trousers go a really long way–I now have 2 pairs of this Gap pair and I love them. Last, I highly recommend a comfy pair of ankle boots (I waterproof mine with this spray and I’m good to go).

Blazer (similar)

Sweater (get $25 off if you want to try anything from Brass using code REBECCA25)

Pants (this year’s version)




When the weather is dry I love a pair of loafers, plus you can layer them with socks for peak teacher vibes. Also, can I just say that with the amount of walking I have to do to get to any classroom, the shoes better be comfortable or they are going back to the store. These shoes are truly one of the only pairs I own that required zero break in time, I’m now contemplating several colors. I really want my overall work look to be relaxed yet polished so I toned my suit blazer and loafers down with my favorite pair of loose jeans (also amazing because I can layer leggings under them when I’m freezing).

Blazer (similar)

Eyelet top (simlar)




There you have it! Three easy outfits when the temperatures drop. Do you have any favorite teaching clothes in the winter?

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