With a chill in the air and the trees changing their colors, one thing is certain: it's time for boot season. While you're swapping out shorts for jeans and tees for sweaters, add to your autumn arrangement with the Simi Chelsea boot from Crown Vintage. What they are : A pair of classic boots with a round toe for a sleek edge. Elastic gores provide pull-on comfort, and the chunky lugged outsole holds up to slick walkways. Why you’ll love them : Simple styling makes this pair easy to wear with any outfit combo. How we’d wear them : Match the Simi with a sharp pair of black straight-leg trousers for a Matrix-like inspiration, or add these with some distressed denim for a more classic feel.