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  Respect the order:
  The key to layering is to start with the softest layer and work your way out to the most durable.

Add a little color with easy-going outerwear like this cotton bomber in a dusty green. Of course you'll zip it up over your off-duty tees and hoodies, but feel free to stack it over a button-down.

Gap, $70

A sturdy shirt that can be worn on its own with the sleeves rolled or buttoned-up over a T-shirt and under a cardigan or jacket. It also makes for a lightweight shirt jacket that you can sport over a henley.

Denim & Supply, $98

Falling somewhere between a tailored blazer and a field jacket, this knit cotton jacket is a relaxed, breathable alternative to your standard structured sport coat. But it's just as easy to dress up or down.

Todd Snyder, $395

A weatherproof color-blocked cotton trench that won't look out of place on cold, wet days in the city and looks even sharper when layered over a suit or with a pair of jeans and your standard shirt/tie/blazer.

Brooks Brothers, $348

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