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St. Bernard's 17th Annual Horse Show
Credit: Ron Galella/WireImage

Back in the '70s, one of the things I most looked forward to in autumn was The Monmouth County Hunt, an annual fox hunt, steeplechase, and massive tailgating party. It was held at the end of October on the grounds of the Middletown, New Jersey estate owned by Mr. Amory Haskell, and it was a great excuse to pull out your best country weekend-wear. Needless to say, tweed jackets, houndstooth checks, blanket patterns, riding boots, and other equestrian styles were de rigueur.

It’s a classic look that still works for women of all ages. The key to pulling it off is not to be too literal unless you are actually planning to ride. A skinny pant tucked into riding boots looks great with a chunky turtleneck sweater. A tweed blazer or blanket-striped coat can pair beautifully with leather pants. Accessories such as a leather saddlebag, saddle-stitched leather bracelet, equestrian-print scarf or horse-shoe pendant are worthy investments since they will never go out of style. Add one or two to a white shirt and jeans for a rich, but effortless weekend look that works wherever your home turf happens to be.

The Perfect Equestrian Weekend Look

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Shop it: Madewell blanket cape, $148; madewell.com. Alexis Bittar necklace, $155; shopbop.com. Chloé shoulder bag, $1,090; net-a-porter.com. Altuzarra coat, $1,865; matchesfashion.com. Uniqlo oxford, $30; uniqlo.com. Hermès bracelet, $560; hermes.com. Ariat jodhpurs, $210; net-a-porter.com.

Off-Duty Equestrian Style

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Shop it: J. Crew cape, $350; jcrew.com. Rodarte blazer, $2,990; farfetch.com. H&M pants, $20; hm.com. Dsquared2 shirt, $395; farfetch.com. Gucci silk scarf, $440; gucci.com. Ann Demeulemeester boots, $959; farfetch.com.

Photo inspiration at top: Jackie Kennedy Onassis & child at the 17th Annual Horse Show at Vince Lombardi Center in Peapack, New Jersey, 1970.