I'm not a big fan of fashion rules, but here's one I still stand by: No matter where you live, what size you are, or what you do for a living, you need to have a well-cut trenchcoat in your closet. There's no reason to sacrifice style at the onset of rain. You can't go wrong with a classic tan trench, though this season, there are tons of options in of-the-moment pastel hues and head-turning prints. I prefer mine cinched at the waist: totally chic — and easy! — when paired with skinny jeans and wellies (Hunter Boots, shown here, come in wide calf sizes).
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RAIN BOOTS $135, Hunter Boot; hunter-boot.com.