Barbour Beadnell Waxed Cotton Jacket, $399
Fall promises some cool relief after a hot summer, but fall weather (especially in the northeast) can be pretty erratic. One day you're basking in the sunlight of 60 degree weather and the next you wake up to a blizzard— this is not an exaggeration, it happened to me when I lived in Upstate New York. Getting dressed is significantly more difficult when you don't know what weather fall will throw at you, but luckily this Barbour jacket can withstand it all. It is made with waxed-cotton, corrosion-proof zippers, and double-stitched seams to give you a weatherproof finish that is super practical, but attractive too.