Seven Days of Fall | Day 2

The Bean Boot + The Ragg Sock

With all the buzz about Red Wing boots the past couple seasons, people seem to have forgotten about my personal favorite foul weather friend, the Bean Boot from L.L. Bean. Handsewn in Maine with a chain-tread sole, this low-cut moc is the same one Lisa Birnbach featured in The Official Preppy Handbook. While it's also available in a high-lacing model, why not throw on a snuggly ragg sock to keep your ankles warm? J.Crew's got a pair from Vermont that should do the trick. With cuffed selvedge denim, you walk the (thin) line between Brooklyn yuppie and New England boarding school alum.
Bean Boots, $59, llbean.com; J.Crew Camp Sock, $16.50, jcrew.com