A Guide to Classic Preppy Style

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A Guide to Classic Preppy Style

What is Preppy Style? 

Born on elite university campuses, from Oxbridge to Harvard and Yale, the preppy style is characterized by the playful combination of tailored cuts, vintage pieces, and classic sportswear. 

A symbol of modernity, preppy style sought to subvert the suit-and-tie aesthetic of the white-collar class by pairing traditionally tailored clothing with casual sporty attire, finding influence in college sports from polo to tennis, rugby to rowing and so on. 

The fact that, since its inception on the college campuses of the 1950s, preppy style remains a mainstay of the ever-changing sartorial climate is an indication of its innate versatility and timelessness. As far as smart casual goes, preppy style can hardly be beaten.

Shop Crawley Polished Leather Loafers

How to Dress Preppy? 

The essentials for preppy style? Think bold varsity jackets, tell-tale logos, button-down shirts and, of course, the ultimate foundations for your preppy wardrobe: the shoes. 

From penny loafers and sports-inspired sneakers for him, to chunky heeled loafers and Mary Janes for her, get prepped for any smart-casual occasion with our curated collection of preppy classics. 

For Him


Made popular on - you guessed it - Ivy League college campuses, penny loafers were once a casual act of rebellion against stricter societal dress codes. 

Shop Chorleywood Leather Penny Loafers

How to Wear Men's Loafers?

A social chameleon, the loafer takes the top spot as the most straightforward smart-casual player in this line-up.

A pair of black leather loafers or deep burgundy will rarely steer you wrong when it comes to preppy style. Choose a chunky silhouette, such as our Chorleywood loafers, for a modern update. 

To wear with confidence, opt for socks and loafers to maintain the quirky side of preppy style, and pair with straight-leg chinos, plus a varsity jacket for a touch of nostalgia.  

Chunky Lace-Up

Be it a brogue or our Cheadle lace-up shoes, a chunky lace-up is a non-negotiable when it comes to building out your preppy style. Crafted in suede, Cheadle is structured with a piped toe seam and dual eyelet lacing. 

A chunky sole will add definition and weight to your look. Don’t be afraid to experiment with matching and contrasting clothing textures. 

Shop Cheadle Leather Lace-Up Shoes

Typically used in clothing made for hunting sports, tweed, flannel, houndstooth and herringbone pull on the vintage and sports-based origins of the preppy style.

Choose a loose-fitting sports jacket in the above fabrics for heritage-inspired prep. Consider a patterned sock to polish off the look. 

Sports Kit

A preppy wardrobe simply wouldn’t be complete without the addition of a cup sole sneakers

Shop Sutton Leather Trainers

Take the Sutton leather sneakers for example. Traditionally constructed in leather with a flexible rubber sole, Sutton takes inspiration from the styles of days gone by, updated in a modern iteration set to withstand the test of time.

The safest option for those looking to dip their toe into preppy style without fully committing to the aesthetic, it’s long been understood that a classic white trainer is a smart-casual staple. 

If you are looking to keep it at least a little preppy, an OBDS (that’s an Oxford button-down shirt) and chinos make smart-casual dressing as easy as strolling across the college green.  

For Her

Modern Mary Janes

When we say preppy, you’d be forgiven for thinking back to your old school uniform shirt, skirt, and Mary Jane shoes. Recently, however, Mary Janes have experienced a renaissance, now presented in chic silhouettes suited to the modern woman and the pace of modern life. 

Shop Luciana Square Toe Mary Janes

From the playground to the halls of haute couture, modern Mary Janes, including our own Luciana, subvert the traditional child-like style: note the addition of sophisticated details, such as a square toe and slight block heel.

Style with an oversized blazer and a mini skirt to keep up with Luciana’s modern appeal (bonus points for white socks).

High Achievers


How to style women's loafers

When it comes to women’s loafers, there are two routes to take to achieve preppy style.

Shop Genevra Heeled Loafers

First, the heeled loafer. Genevra are our chunky heeled loafers carved from smooth leather, with a piped toe and chunky chain detail. 

When it comes to styling chunky heeled loafers, let midi skirts in plaid or dogtooth patterns be your sartorial guide. 

Shop Darra Chunky Penny Loafers

The second route sees classic leather loafers elevated on a rebellious chunky sole. Darra features a cleated sole and grained leather upper. 

Contrast with softer fabrics, such as a cable knit jumper and an oversized sports blazer with striped detailing. 

Shop Lidia Leather Brogues

Heritage Inspired

A classic brogue will serve you through smart and smart casual occasions alike. Traditionally constructed after a more masculine style, women’s brogues master the subversive and playful edge necessary for preppy style. 

Our Lidia brogues are keen to show off their classic craftsmanship, with a wingtip and full brogue detailing across the upper. 

 To offset the measured style of the heritage brogue, a rugby jersey or sweater vest and straight-leg jeans will set the right smart-casual tone. 

Shop Lidia Leather Loafers

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