Need a wardrobe update to take you into Fall? Start right here, where we’re giving away a complete outfit (pictured below) to one reader, courtesy of Silver Jeans Co. Here’s how to win:

In the comment section below (or in an email response to rfarazmand[at]breakmedia.com), describe your favorite clothing item in a few sentences or less. Is it a faded army jacket your dad handed down to you? Or maybe a pair of jeans you refuse to wash because it would change the way they feel? We all have a piece of clothing we’ve grown attached to, and we want to hear about yours. Submit your entry by September 23 at 12pm EST. We’ll pick a winner at random later that day, and he’ll win each of the items pictured below.

Plaid button down (list price: $69.00)

Cargo jacket (list price: $120.00)

Konrad slim-straight jeans (list price: $75.00)