Long live preppy style staples like the leather loafer and navy blazer

Polo, tennis, golf. Lacrosse. Preppy style may have originated in the American Northeast, around elite universities and exclusive sports, but the aesthetic and its hallmarks are now a global phenomenon, inspiring designers and creative teams across varied backgrounds. From Thom Browne to Celine, influences of classic preppy style are apparent along a wide spectrum of variations and mashups. Man Repeller wrote back in April about the resurgence of preppy style. We love it because it’s perfect for the fall and transitional weather and highlights America’s contribution to global style. 

The Leather Loafer

The leather loafer actually originated in Norway as a sort of mocassin shoe inspired by the rawhide footwear of Native Americans. Only when a New Hampshire family (the Spauldings) began crafting a variant called the loafer, and G.H. Bass coined the “penny loafer,” did the form of footwear take hold in America.

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women’s preppy style celine loafers
The best women’s loafers of the moment come from Celine, and they’re a quintessential part of preppy style.

Today, no one is doing leather loafers for women quite like Celine. Under the new creative direction of Hedi Slimane, in a sort of “looking back to look forward,” the brand has introduced the Luco loafer in timeless staple colors like dark burgundy (a.k.a. oxblood) and black and white (a.k.a. tuxedo) on polished calfskin, as well as a variation in black suede.

They’re constructed using the Blake method, which is closely associated with the high quality process of Italian shoemaking. And fringe or no fringe, this season they’re all embellished with the brand’s resurrected Maillons Triomphe signature gold chain, a nod to the lengthy heritage of the French label founded in 1945.

The Navy Blazer

While not exclusively from a preppy background, the navy blazer is a staple of preppy style with hundreds of variants to consider, from this double-breasted Barena to this deconstructed-sleeve, wide-lapel Margiela piece. The brilliance of the navy blazer is that it’s universally flattering on skin tones and torso shapes, but softer than black, and is largely compatible with other colors—especially crisp white, gray, lighter blue, and even green and tan.

women’s preppy style navy blazers barena maison margiela weekend max mara
The navy blazer is a staple of preppy style, no matter the form it takes. From left to right: double-breasted by Barena, deconstructed by Maison Margiela, or velvet by Weekend Max Mara.

We like this single-breast one from Max Mara in navy velvet. It’s tidily cut and has a warmth and softness that’ll offset any fall temperatures you might encounter.

The White Button-Down

Thom Browne is perhaps the best purveyor of upleveled preppy style, with an endless well of cheeky interpretations on the white button-down shirt. Almost all of them incorporate his signature grosgrain stripes in red, white, and blue, either on the placket, around the sleeve, or as an oversized bow embellishment. He even fashions the oversized white button-down shirt as a shirtdress, favorited by celebrities like Anne Hathaway and Rihanna. Though they may sometimes be outlandish, his designs are timeless, changing only marginally season-to-season. The shirts themselves are constructed in Italy and Japan of sturdy cotton broadcloth and will last a decade or more.

women’s white button down shirt thom browne
Thom Browne is a master of the white button-down shirt, putting his unique spin on it each season.

The Pleated Skirt

Aside from cotton chinos and classic denim jeans, the pleated skirt is a preppy style staple with perennial appeal. Designers from nearly every background have a take on the pleated skirt: maxi and mini, plaid and printed, even monogrammed. Work some fall color and swooshy movement into your preppy style with this autumnal forest green Max Mara Studio number or uplevel your prep with this darkly romantic, baroque-inspired Valentino skirt from the Undercover collaboration, sure to fit in at an art lecture. 

women’s pleated skirts gucci max mara valentino golden goose
Pleated skirts come in many formats, from 1970s monogram to nautical-inspired. Pick your favorite, from left to right: Gucci navy and off-white monogram cotton-canvas A-line skirt with feline head gold buttons, Max Mara Studio finely pleated forest green skirt, Valentino x Undercover crêpe de chine Lovers Pattern print skirt, Golden Goose Ayame taupe cotton skirt with technical drawstrings.

On the other hand, you may want to pay homage to the sporty side of preppy with this khaki Golden Goose Ayame skirt in broad pleats, embellished with technical drawstrings that evoke sailing off the coast of Cape Cod (one of the epicenters of preppy style).

Plaids and Stripes

Lest we overlook this very central motif of preppy style, there are a million ways to integrate plaids and stripes into your look without looking too stuffy or too juvenile. Bold stripes can be beautifully bold, but they can also be distracting, not to mention lengthening or widening to the silhouette. Stick to softer stripes in neutral tones that mesh well with everything—like this Brunello Cucinelli alpaca and cashmere-blend scarf with varying stripe widths. Quidditch, anyone? 

women’s plaid stripes brunello cucinelli riccardo comi massimo alba loewe
Wearing plaids or stripes doesn’t have to look juvenile. These examples are all appropriate for fall preppy style, no matter how long you’ve been out of university: a neutral-toned Brunello Cucinelli scarf, a maxi-striped knit cardigan from Riccardo Comi, a muted black and cream plaid blazer from Massimo Alba, and a lighter, more cheerful plaid print dress from Loewe.

Work your stripes another way with this cream and black maxi-stripe oversized cardigan, a knit style that’s another mainstay of classic prep-school style.

Plaid may the least-loved motif here, but we adore its execution by Massimo Alba, a master of contemporary Italian luxury, seen here in a double-breasted cream and white plaid checked blazer. It would look at home in any college classroom, or on a Milanese runway. Outside of class, a candy-striped plaid and belted dress will do just fine to engender the preppy spirit. Loewe, led by British designer Jonathan Anderson, has one that looks equally suited for polo matches and festive holiday gatherings.

How to Wear It

Prep style is classic, but can look like a costume if applied too heavily. Out of the five thematic elements above (loafer, navy blazer, white shirt, pleated skirt, and plaid/stripes), choose up to two or three at a time to channel your inner prepster. For example: loafers with denim jeans, a white button-down, and a navy blazer; a pleated skirt with a striped cardigan; a white shirtdress with loafers and a satin headband.

Long Live Prep

Ever the antithesis of streetwear, preppy style is a timeless aesthetic that has influenced designers and collections far beyond its humble beginnings in the Ivy League. We love it because it’s at once classic Americana and a global anti-trend, with interpretations and reimaginations that maintain its freshness season after season. This fall, take a break from logo-mania and consider something with a rich history. You may even find chic vintage pieces in your mother’s closet!

Discover more How to Wear It posts: What to Wear on a Weekend Getaway, How to Mix Pinks Like a Pro.

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About the Author

Alex English is the Head of Content Marketing at italist.com, building on a lifelong passion for fashion and luxury. After publishing a lifestyle blog for nearly ten years and obtaining an MBA in Milan at SDA Bocconi, one of Europe’s top business schools, he joined the italist team in 2019. His work since then has focused on upper-funnel messaging, brand storytelling, establishing italist as a thought leader in the space, and enriching the customer experience on the platform. Find him on LinkedIn.