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Instead of a dark plaid or solid under a sweater, try something a little brighter like Trovata’s fall flannels. Instead of a heavier coat, combine a soft Shetland wool sweater with a mid-weight jacket. A layered fall look is shown here with the Shipley & Halmos fairisle sweater paired with Gant Rugger’s canvas moto jacket.
Don’t write off khakis because of bad cubical-garb associations. Dockers have reinvented the genre, modeling their Alpha Khaki after denim and updating the styling with flat front pockets (no pleats!) and a tapered leg.
Tretorn’s Klipporone boot is slim to the foot while providing ample warmth and weather protection. This way you can get from home to work and then out to dinner without changing your shoes. They even come with tonal brown laces so the boots can work with a casual suit, or office attire. Or go with the rubber Vinter boot for an easy slip on option.