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Martens womens 1460 smooth boots, $135, drmartens.com
What you need: A black dress, a plaid shirt, scarecrow makeup, and a straw hat if you have one
A chunky heel makes them easy (and comfortable) to walk in, and they even have a cushy sole to cradle your feet all day long
These jogger-style chinos maintain the sophisticated tailoring you love in a regular chino while adding the relaxed, laid-back feel of joggers thanks to their cuffed ankles and elastic waist
The silicone tape on the inside ensures a secure fit, while the invisible back zip and hook and eye closure make for easy wear
