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A trench coat feels like a must-have and I personally love my houndstooth print similar to this Mango one as it goes with a variety of outfits, but always looks well put together. Another piece you have to have in your wardrobe is a checked skirt especially one that can be worn with a chunky cable knit jumper.
I always scour through Etsy when looking for some unique finds and I found this Gingham Dress by a company called Literary Garments and I think it perfectly fits in this aesthetic. One of my favourite brands on Etsy is Hearts and Found and their Mary Dress in Walnut Linen looks like it'd fit in my wardrobe perfectly.
If you want some Winter dark academia outfit inspiration then I have compiled a list of my favourite finds below: