A Weekend In... Watch Hill, R.I.

WATCH HILL, R.I.: Newport's quieter sister, Watch Hill abounds with rambling manses and old-school charm. Pick up sandwiches on the way in at The Cooked Goose in Westerly (try the "C.M.R." or the "Aphrodite") before hanging your hat at the Ocean House, a beautiful seaside resort that was recently restored to its former grandeur. (Bring dress whites for the regulation croquet court!) Après beach, take a spin on the Flying Horse Carousel and check out the gorgeous yachts docked at the Watch Hill Yacht Club. After washing the sand off, grab dinner and drinks alfresco at the Olympia Tea Room. When you're ready to go, head out by way of rail, air, or sea.

Clockwise from top left: Canvas coal bag by ACL & Co., $68, here; J.Crew plaid shirt, $68, in stores; Cartier Tank Solo watch, $2,300, in stores; Asprey propeller keyring, $270, here; Sperry Top-Sider boat shoe, $75, here; Hermès "Yachting" beach towel in horizon blue, $180, here; Wölffer Estate 2010 Rose, $16, here.

Loafing Around

First 80+ degree day in DC called for brown linen pants from Polo by Ralph Lauren and Hermès slip-ons. Photographed in McPherson Square.

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

Cordovan Shoes: A Primer

There's no doubt in my mind that the phrase "Shoes make the man" absolutely holds true, even today. Jeans and a white tee can go from boring to chic with the right pair of distressed wingtips. Conversely, even the most pricey bespoke suit can be completely spoiled with a pair of cheaply made dress shoes. A classic pair of leather-soled lace-ups, wingtips, or loafers, when cared for properly, can often last as long as 10 years. One particular type of leather has been known to outlive even its wearer: shell cordovan. (Not to be confused with the color cordovan - the burgundy hue that shell cordovan shoes are often dyed.) It's tough as nails, and especially water resistant - and for a good reason. It's made from the shell, or hind quarters, of a horse. While it takes time to break these suckers in, once they mold to your foot, they can be as comfortable as wearing nothing at all. Yes, they are quite expensive, but honestly - by using cedar shoe trees, polishing them by hand, and getting them resoled every few years, you're bound to see some return on that investment. Here are a few of my favorites:

Darlton Tassel Loafer (pictured above), $795, ralphlauren.com

In the chukka boot format, cordovan makes particular sense, as it will keep the rain from getting your socks too wet this fall. Alden Cordovan Chukka Boot, $568, aldenshop.com

Who can resist a classic penny? P.S., if you're not feeling the burgundy color, these also come in black. Please, don't put pennies in them. It isn't 1958. Brooks Brothers Cordovan Loafer, $598, brooksbrothers.com