Preppy Outfit Ideas for Men: From Ivy to Everyday

Within the halls of Ivy League universities, surrounded by textbooks and the exchange of academic ideas, a unique fashion style was born. It was a preppy style—a sartorial choice that conveyed the wearer’s aspirations and position within the social fabric. Fashion in this sense was a conscious decision, a sort of badge of identity. With roots deeply embedded in the elite educational institutions of the East Coast, the preppy look transcended clothing—it was a statement of tradition and values, reflecting both intellectual pursuits and the social codes it embraced.

Men’s preppy fashion can be traced back to early 1900s Ivy League students, prioritizing a polished appearance marked by clean lines and patterns. Key pieces of the preppy aesthetic include blazers, polo shirts, button-downs, khakis, and loafers, often with nautical influences and stripes. Accessories, belts and caps, play an essential role in the look. While preppy fashion has been around for over a century, the term “preppy” gained traction in the American fashion vernacular during the 1970s and 1980s. Today’s preppy menswear prioritizes premium materials and classy cuts—a kind of formal dressing with an easy-going attitude. 

Now, let’s explore how to dress preppy and adopt a modern look that feels fresh while honoring its classic roots.

Button-down shirt

Shirting is a fundamental aspect of men’s preppy style, but there are some requirements—seek out thicker, more textured fabrics, ideally in a basket-weave Oxford style. This choice offers a more relaxed feel—rather than looking like you’re waiting to throw on a suit jacket. A button-down collar is a huge plus. From there, the real fun lies in layering over your shirt. After all, you can’t construct a stylish look without a solid foundation.

Denim on denim is not preppy strictly speaking, but it can become a part of this aesthetic with a proper button-down. The Checked cotton shirt from Les Deux, for instance, makes for a perfect base layer. Add the Classic denim jacket from Citizens of Humanity on top and a matching pair of jeans to create a clean look with a casual core.

Casual blazer

A well-chosen blazer is essential for a men’s preppy outfit. When selecting the right one, you don't want anything overly polished or too snug—aim for unstructured designs with rounded shoulders made from sturdy fabrics such as wool, corduroy, or heavy cotton. Look for sporty details—notched lapels or patch pockets—that add character. Once you've found the ideal blazer, pair it with jeans and a rugby shirt, layer it over a denim shirt, or use it to elevate a tucked-in tee with pleated trousers.

The Casual wool-blend blazer from Tiger of Sweden is a perfect match, and you can dress it up with suit trousers or dress it down with jeans. We suggest going casual and combining it with the Straight jeans by Dirk Bikkembergs.

Polo shirt

The polo shirt was originally crafted for tennis players in 1926 by René Lacoste, but it quickly became a part of the preppy wardrobe due to its sporty grace. Its popularity soared in the 1930s when polo players began to actually use it. The polo shirt's remarkable versatility allows you to wear it with a blazer or shorts, perfectly capturing the preppy spirit.​

An embodiment of Ivy League preppy style, the polo is a must-have for any fashion-conscious man. For our look, we teamed the Contrast-collar polo shirt with the Tailored jersey shorts from Aeronautica Militare.

Wool sweater

Nothing quite compares to the classic look of wearing a sweater around your shoulders, with the arms playfully tied at your chest. A chunky wool sweater, a staple on Ivy League campuses back in the '70s, goes even beyond. It's soft, lightweight, and wonderfully warm—layer it over a button-down or simply toss it over a tee with chinos. Navy and gray are safe bets, yet this is a great chance to add color to your outfit.

The Wool pullover from Tiger of Sweden works as an accessory around your shoulders or layered over a button-down—its beige color and chunky knit are ideally suited to the aesthetic. For a modern touch, combine it with the Denim shirt from Les Deux—still preppy but more exciting.

Sweater vest

One of the wonderful aspects of a preppy style is its inherently lighthearted nature. Take the sweater vest—there’s an endearingly playful quality to it, especially adorned with a classic Fair Isle pattern. Throw one on over a white tee for just-cool-enough days or layer it over a shirt and under blazers, cardigans, or even overshirts. Don’t overthink it; after all, we’re talking about a sweater minus the sleeves. 

Check out the V-neck cashmere vest by Johnstons of Elgin—minimalist, versatile, preppy-ready. Layer it over the Striped button-down shirt from A.P.C.—they both boast polished blue shades and are ideal for tonal dressing.

Baseball cap

Focus on specific design elements of a cap that align well with a preppy wardrobe. Opt for a classic design instead of a trucker or camper; six-panel with a gently curved brim are your best bet. Look for subtle retro details like contrasting brims or embroidered logos, as these features speak the same language as other preppy elements.

The Les Deux caps collection offers plenty of stylish preppy options in various hues and styles, such as the Embroidered cap with a contrasting embroidered logo on the front. We recommend mixing it with the shirt in the matching dark navy—the Linen shirt, for example, would do the trick.

Chinos

And now every man is thinking: Chinos, I’ve got those. However, the preppy look doesn’t quite come together with very slim styles, which often lean more toward a European aesthetic—especially those ultra-tight, buckling-thigh-seam designs that some gym enthusiasts seem to favor. Instead, aim for a roomier option with a straight or slightly wider leg. Look for a pair made from cotton twill that will maintain its shape and comfortably break in over time.

The Casual chino-fit trousers from Tiger of Sweden offer the preppy fit we are talking about—not too slim, not too wide. Add a crisp shirt on top and layer the Half-zip sweatshirt over it. It’s almost like a cardigan, but more modern.

Loafers

If you haven't jumped on the loafers trend from the past couple of years—it’s not too late. In fact, your timing might be perfect—every reputable menswear brand currently offers stylish options. Choose classic penny or tassel loafers with a rounded toe rather than almond-shaped ones. Resist the urge to go sockless; instead, take this chance to show off your bold printed socks.

Hereu’s pairs are our fave thanks to their premium quality and unique Mediterranean features. Select the Slip-on loafers for your classic ensembles and the Suede lace-up loafers when you’d rather go for boat shoes.

Braided belt

When we mention that great preppy hinges on the details, this is exactly what we mean. A braided belt, preferably made from leather or a synthetic material, is your quiet hero. Opt for a simple design in black or brown, as these shades pair well with any chinos and jeans. As summer gets closer, switch to a two-tone or a more vibrant option.

Have a look at Les Deux’s Webbing belt—perfect for a newbie in preppy fashion, as it doesn’t have any bold accents and is easy to style. Combine it with the Regular suit trousers to begin with. Later, you’ll want to pair it with jeans, chinos, and shorts, and we encourage you to do so.