How To Style Classic Preppy Loafers

Your grandpa's old favorite shoe style might be one of the chicest footwear options out there, with a few updates, of course. Preppy style is finding its way back into the mainstream, with many playing around with the classic details and giving them a more modern twist.

Traditionally, preppy style featured tailoring and vintage pieces, and was originally spotted on campuses of elite universities like Harvard and Yale, according to Jones Boot Maker. Modern preppy style still evokes a feeling of the traditional elite but is often more DIY and thrift store friendly, says Fashion Magazine. Similarly, many are putting a personal spin on the preppy look by maximizing accessories and including more colors.

One feature of preppy style that many are adopting is a stylish pair of loafers. Some have heels to create a more formal look, and others have lug soles, which can add a little edge to an outfit. A classic neutral or a statement hue, dressed up or down, preppy loafers are a must-have addition to your wardrobe.

Casual blazer and chinos

An outfit that mixes casual and dressy is the perfect way to show off a pair of loafers, suggests A Well Styled Life. Consider this a look that you can wear to work and then out with friends afterward. For work, add a blouse, and for more casual outfits, a stripped Breton t-shirt. These classic pieces complement the traditional feeling of loafers and the shoes elevate an understated outfit.

A retro touch with socks

Loafers bring a touch of retro even when they're a modern pair. Add even more of a retro feel to an outfit by wearing loafers with socks, says Upstyle. This can be an incredibly chic look and is favored by the French, according to Leonce Chenal. White and black high socks add a classic element. But you can add frills, sheer socks, or patterns to add a cute little detail.

Laid back with jeans

For a weekend style, pairing jeans with a pair of preppy loafers can help elevate the outfit. Boyfriend, mom jeans, and baggy jeans offer a relaxed look, says Shoe Tease. But straight-leg jeans can add a bit more structure to an outfit. Wear jeans with a t-shirt, sweater, or button-down to finish off the style.

Lean into preppy

Loafers are a staple in preppy fashion, so why not lean totally into the preppy look when creating an outfit? When people think of preppy style, the image that comes to mind is usually representative of New England preppy. Think button-downs, mini skirts, and turtlenecks, suggests Chic Pursuit. Matching sets, tennis skirts, and cardigans are also favorites of preppy style. Modern preppy styles takes the classic aesthetic and adds updated silhouettes and fun colors.

Show leg with shorts

If you're one to show off your leg, then you might want to consider pairing your loafers with shorts. This is an outfit combination you can wear all year round. In colder months, add a pair of sheer tights under the shorts to help combat the cold. Opt for pleated shorts, which can give your outfit some structure and a clean-cut sophistication that allows you to dress up a casual look, according to The Beau Life. A longer option also creates a menswear feel that can look incredibly sleek and chic.

Feminine midi-length

When done right, a midi-length skirt or dress can look super feminine. From casual to formal, there are plenty of options for a midi-length outfit and pairing it with loafers gives the outfit a fashionable element. The length can be awkward, but nailing the look is all about balancing the outfit, says Kate Waterhouse. If your skirt is flowy, a tighter top helps even it out. And adding waist definition helps gives you some shape. Opt for a belt that matches your loafers to keep the outfit cohesive.