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ALL IN THE DETAILS: The Classic Trench

As the weather gets chillier in Chicago, the kids at my school tend to develop and stick to a cold weather uniform of sorts. For some girls that means chunky sweaters, leggings, Converse shoes and puffer coats. Other girls keep it dressy in sweaters, skirts, tights, heeled boots and wool coats. Guys usually stick with heavy knits, jeans, chukka boots and puffy jackets. As for me, my go-to cold weather attire is a turtleneck, jeans, ankle boots and a huge parka.

This Fashionisto masters cold weather dress in an outfit that is comfortable, understated and polished. The key piece of the look is his structured trench coat. This classic coat style is an investment piece that every gal and guy must own. A trench can be worn in three out of four seasons of the year—depending on where you live—and can either be dressed up or down.

This Fashionisto keeps his look casual by combining a simple black sweatshirt with a pair of cuffed black skinny jeans and black leather work boots. He breaks up the monochromatic look with the iconic trench that instantly polishes the entire outfit. He accessorizes with an Yves Saint Laurent logo-print backpack and reflective sunglasses.

How To: A classic trench coat can dress up any look in a minute. Guys can recreate this look by throwing a dark colored trench over a basic sweatshirt, skinnies and boots. Ladies can wear the iconic coat over a loose turtleneck, boyfriend jeans and heeled ankle boots.