New month and yet another chance to win the fabulous items featured on the cover of Lucky magazine. For the October issue, Lucky nabbed Jessica Simpson. Inside, the singer opens up about her must haves for Fall, including fringe boots and a "big, manly watch" — she should consult our macho watches!

Now, let's get down to business. Head over to LuckyMag.com for your chance to win what Jessica's wearing. The goods include her Fendi blazer, Temperley silk tunic, and all of the makeup. The total value of the merchandise is nearly $4,500 (dang). Enter today.