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The preppy look originated in the early 1900s with collegiate and prep-school menswear (thus, the moniker). Signature items included blazers, polos, chinos, oxford shirts, tennis sweaters,
loafers. Over the decades, fashion designers ranging from Ralph Lauren to Tommy Hilfiger and Tory Burch have celebrated preppy style. _The Preppy Handbook_, published by Lisa Birnbach in
1980, was intended as a kind of send-up — but it also served as a how-to manual for many people unfamiliar with the look. Today’s sporty, slightly rumpled preppy aesthetic is a bit more
androgynous, sexy and playful. Think more Diane Keaton in _Annie Hall_ vs. anyone named Muffy. (In other words, skip the grosgrain headbands, cashmere twinsets and pearls. We’re not taking
about the pink-and-green Lilly Pulitzer kind of preppy here.) This is about clothing inspired by the yacht club, tennis club, country club or college campus — but, today, these items push
the old house rules. Their fit might be slightly off ... the blazer may be a little shrunken or oversized; the chinos, slouchy or cropped. It’s a terrific look for autumn weekends, whether
you spend them browsing at an urban flea market, meeting girlfriends for lunch or watching your grandkids’ soccer games. HOW TO PULL IT OFF Add one decidedly non-preppy element to your look:
Say, wear a sexy silk shirt half-tucked into baggy khakis. Or pair your fisherman sweater and cropped jeans with a kitten heel. You can, of course, embrace the whole boyish aspect: blazer,
striped shirt, chinos, crewneck, driving shoes. But remember to wear lipstick — and maybe a chain necklace, or some stacked bracelets, or small drop earrings. One feminine detail goes a long
way. THE ELEMENTS OF PREPPY STYLE: WORTHY OF INVESTMENT BECAUSE THEY STAND THE TEST OF TIME THE NAVY BLAZER A well-tailored jacket upgrades your basic jeans and chinos — and also pairs
beautifully with trousers or a pencil skirt for more formal occasions. Left to right: Talbots Houndstooth Blazer in Ivory Multi ($179, talbots.com); Banana Republic Icon Blazer in Preppy
Navy ($108, bananarepublicfactory.gapfactory.com); J. Crew Factory Herringbone Wool-Blend Schoolboy Blazer in Antique Navy/Ivory ($129, factory.jcrew.com) Talbots; Banana Republic Factory;
J. Crew Factory THE CABLE-KNIT SWEATER A textured knit adds visual interest to your look when worn with casual pants. Push up the sleeves for extra panache. Left to right: Brooks Brothers
Cotton-Linen Blend Tennis Sweater in Oatmeal ($124, brooksbrothers.com); Tommy Hilfiger Cable Knit Sweater in Desert Sky ($52, usa.tommy.com); L.L. Bean Women’s Bean’s Heritage Soft Cotton
Fisherman’s Sweater in Cream ($89, llbean.com) Brooks Brothers; Tommy Hilfiger; L.L. Bean THE SLOUCHY CHINO Cut more like a trouser than your standard-issue khakis, these can work with
sneakers, loafers, even slingback pumps. Left to right: J. Crew Sailor Heritage Chino Pant in Natural ($93, jcrew.com); Gap Twill Wide Leg Pants in Chino Beige ($31, gap.com); Vineyard
Vines Pleated Wide Leg Chino in Officer Khaki ($158, vineyardvines.com) J. Crew; Gap; Vineyard Vines THE STRIPED COTTON SHIRT A crisp button-down in a menswear stripe spells polish. Pop the
collar to up the preppy factor. Left to right: Lauren Woman Striped Cotton Shirt in White/Indigo ($95, ralphlauren.com); Vineyard Vines Bayview Poplin Shirt in Rhododendron/White ($98,
vineyardvines.com); Boden Sienna Cotton Shirt in Fine Blue Stripe ($68, bodenusa.com) Ralph Lauren; Vineyard Vines; Boden THE SUEDE DRIVING MOCCASIN Lightweight and flexible, the driving
shoe was an instant status symbol for men when it was introduced in Italy in 1963. Today, it still hints of prestige — and can add some fun color to your weekend neutrals. Clockwise from
top left: M. Gemi The Felize Suede in Pink Coral ($198, mgemi.com); Ann Mashburn Driving Moccasin in Dark Camel Suede ($295, shopmashburn.com); Eastland Patricia Moccasin in Green ($85,
dsw.com) M. Gemi; Ann Mashburn; DSW FINAL WORD Make no apologies for dressing like a prepster even if you aren’t. Like F. Scott Fitzgerald’s character Jay Gatsby or fashion designer Ralph
Lauren (formerly Ralph Lifshitz, born and raised in the Bronx), we’re Americans — we reinvent ourselves!