Buy It Now at J. Crew, $60
Last winter, dudes wore running sneakers with everything. With the growing trend of mixing comfort and style, sweatpants have been reinvented with a slimmer fit, shorter cuffs, and more pockets. That means you can wear them with just about anything, and we think you should. Throw them on under a duffle coat, wear them with an untucked oxford shirt and denim jacket above. Just be sure to wear them with sneakers. Sorry, sweatpants and proper footwear still doesn't look good.