Preppy Style for Men: Our Unofficial Handbook for this Heritage Classic 

Do you have a navy blazer tucked away in your closet? How about a polo shirt (or two)? Chinos? If you’ve answered yes to any of these questions, then you’re on your way to mastering one of spring 2022’s biggest trends. Let us reacquaint you with men’s preppy style. This all-encompassing aesthetic effortlessly combines timeless styles with pops of bright colors and just a hint of irreverence. It’s all about upping your game for casual attire and approaching formalwear with a more relaxed point of view. OK, aspiring prepsters, grab a seat (G&T optional) and make room in your wardrobe for contemporary takes on the classics. 

The Origins of the Preppy Aesthetic

As fashion trends come and go, all things prep have withstood the test of time. With trendy updates to tried-and-true classics, the elements of preppy style for men are an integral part of our wardrobe. In fact, our modern-day athleisure wear can trace its roots to this approach. Those loungewear essentials and jogger sets you’ve been living in these past couple of years? They may scream street style, but their origins are prep all the way. And it’s not just the leisurewear you’re sporting on repeat lately. That navy sports coat you grab for weddings, interviews and date night? It, too, after all has the prep movement to thank.

“Preppy clothes are built to last, since they certainly won’t go out of style.” — Lisa Birnbach

The word preppy comes from the preparatory school dress codes that ushered in this fashion aesthetic. A century ago, the uniform staples and Ivy League styles found on campuses inspired a relaxed take on traditional menswear. Think wardrobe heroes like Oxford button-down shirts, loafers and cable-knit sweaters. Moreover, these quintessential collegiate pieces borrowed from vintage British university traditions. Through the decades, this academic look gained a wide following. Lisa Birnbach’s “The Official Preppy Handbook” introduced prepdom to a new set of enthusiasts in 1980. The hallmarks of men’s preppy style originate on the loafered heels of British scholars, 80s icons and a whole lot of southern charm. It’s not just clothing, it’s a subculture. Let us be your guide as we break down the most popular preppy styles. 

British Preppy Style for Men

The casual apparel of students from Oxford and Cambridge universities inspired today’s modern business and everyday casual wear. British preppy style for men effortlessly combines professorial pieces like tweed blazers with sports attire. This ingenious mixing and matching revolutionized the way men dress over the last century. It also laid the foundation for both prep styles and various types of business attire. Go-tos include Barbour jackets, blazers, rugby shirts, chinos and repp ties. Worsted wool, tweeds and plaids reign supreme. 

Men’s preppy style incorporates the athletic wear of Britain’s most treasured pastimes. Rowing and horseracing are two prime sports that influence this aesthetic. From the Henley Royal Regatta to Royal Ascot, the bright colors, striped patterns and single-breasted blazers are preppy staples. To take this style for a spin, pop on a grey flannel herringbone jacket over a color block rugby shirt. Round out your ensemble with midnight blue slacks and boat shoes. You’ll be able to roam from the spectator stands to drinks with friends in a jiff.

Expert style tip: Did you know blazers were first designed for rowers? Constructed from flannel with a loose cut, these iconic jackets also came in a variety of colors and patterns. These distinctive coats allowed you to easily spot your team during races. Before long, the outerwear that kept rowers warm during early mornings on the water made it to dry land.

80s Preppy Style for Men

The prep movement gained a strong foothold in men’s fashion over the 20th century. American prepsters were popping up all around, including President John F. Kennedy and Hollywood legend Paul Newman. Likewise, styles were spotted on campus, in the office, at the stadium and everywhere in between. Enter 80s preppy style. This era of men’s fashion, known for its bold designs, accelerated the boundaries. With the emergence of sportswear designers like Ralph Lauren, affordable luxury in brightly colored polos and crew neck sweaters became accessible to everyone. 

Preppy style outfits for men from this decade include khaki pants or shorts paired with bright polo shirts. To finish this look? A pair of topsiders and a cable-knit sweater tied around the neck. Classic color combinations comprise petal pink with kelly green and soft yellow with bright blue. Looking for a more contemporary take? Swap the sweater for an on-trend and slightly oversized sweater vest. Not ready for polos in lively and luminous hues? Opt for neutrals. The preppiest of them all? Hands down, a chambray shirt. This lightweight cotton fabric goes with everything and is equally polished and relaxed. A prep must.

Southern Preppy Style for Men

Let’s head south, to Palm Beach. Southern preppy style starts in this well-heeled Florida city by the sea. The coastal elements found in preppy style for men are right at home here. This southern sensibility boasts pastel colors and lightweight materials. Madras and seersucker are key fabrications that offer tons of polish and sophistication while keeping you cool. These lightweight kinds of cotton are breathable, making them ideal for warm-weather wardrobes. Traditional plaids and stripes reinvented for summer? Sign us up! 

For a southern preppy style outfit for men, don bright madras shorts. Balance out the punchy plaid hues with a solid linen button-down shirt and bucks. What are bucks, you ask? A staple in any prep’s shoe collection, summery suede bucks, or Oxfords, are lace-up shoes with a rubberized sole. We generally recommend a no-show sock to pull off the sockless look that prepsters rock all summer long. Now, that’s a way to put a little prep in your step.

Preppy Style for Men: Clothing for Every Season

Are you up to speed on how preppy styles arrived on the sartorial scene? Well then, it’s time to break it down by season. Incorporating men’s preppy style outfits year-round is a breeze. A prep is always on the go, and staying active is the name of the game. Lucky for prepsters everywhere, designers have reimagined preppy wardrobe wonders for all occasions and climates. Whether you’re the captain of the team or in the stands, we’ve got you covered for whatever the weather brings.  

Preppy Style for Winter 

There is no shortage of activities to keep a prep entertained during winter. While the hours of sunlight may be minimal as the mercury dips, the season is filled with merriment. From fireside holiday gatherings to braving the chill when hitting the slopes, preppy style for men in winter is something to dress up for. This time of year really lets you showcase the best of your wardrobe. From longline camel hair coats to waist-skimming peacoats, there is a layer for every occasion. Don’t forget about your accessories. Remember to wrap a plaid scarf wrapped around your neck and tuck a pair of vegan leather gloves in your pocket.

The holiday season in winter offers an opportunity to have fun with color, pattern and textures. When thinking about how to dress for a holiday party, stick with the classics. Just add a little flair. Give your khakis a break and start your look with a pair of dark green corduroys. Add a striped button-down shirt, a cozy shawl cardigan and chukka boots for any seasonal shindig. Heading to the mountains to celebrate the New Year? Meet friends at the base of the mountain for an après-ski drink. Wear a black toasty turtleneck sweater with performance pants in a pop of color. We love a burnt orange or bold burgundy. Simply add a puffer jacket and boots. See? Your preppy style men’s wardrobe can traverse winter outings with ease. 

Stand Out in Spring Styles

Spring is all about new beginnings, and that’s especially true for your men’s preppy style wardrobe. With warmer weather and longer days, it’s time to reach for light colors and fabrications. Add subtle pastel shades of pink, purple, blue and yellow to your shirting options to pair with jeans and chinos. Is a spring shower is in the forecast? No worries, add a trench coat or wax jacket—there are a plethora of possibilities.

Nothing signals spring for an old-school prep like the Kentucky Derby. Between the tradition and the pomp and circumstance of it all, this is a time to break out your finest. It’s not just the jockeys wearing their eye-catching silks. Whether you’re headed to Churchill Downs or a neighborhood soiree, you’ll want to dress to the nines. Sip a mint julep in a pair of Nantucket Reds, a blue gingham Oxford and a linen blazer. Add a timeless repp tie, ribbon belt and Derbys, naturally, to complete your look. Go bold and top it off with a hat. Looking for a stylish lid? Choose from bowler, Panama or flat caps to keep the sun out of your eyes. Cheer your pony on down to the final stretch in style. 

Preppy Summer Style Essentials

For hot summer days, you’ll find a preppy fella enjoying the outdoors with their favorite pastimes—boating and tennis. Men’s preppy style for summer not only works for active days but effortlessly transitions to everyday casual staples. Think basics like polo shirts, colorful shorts and seersucker. While perfect for a day at the shore, these essentials likewise do double duty for weekend errands and backyard cookouts. Grounding any prep summer ensemble is the boat shoe. Designed with a rubber sole to prevent slipping on the deck, these kicks are the coastal footwear choice for summer. Wear them sans socks, with a pair of chino shorts and a striped polo. A popped collar lends a preppy flair while also providing a boost of sun protection. Cheers to relaxed dress codes and summer style.

Fall into Autumn Heritage Style

Ready for crunchy leaves, vibrant orange sunsets and football? All things considered, autumn’s arrival is a prepster’s favorite time of year. Between college football season and the crisp fall air for outdoor activities, there’s so much to do. Autumnal preppy style for men includes luxurious layers and a strong footwear game. This is the ideal time to sport your loafers. For chilly fall days, add a pair of argyle socks for extra prep points. Tailgate with alumni in a pair of neutral olive chinos, loafers (penny or tassel), a thermal henley and fleece vest. Borrow from your essential gorpcore outerwear to keep cozy at the game. 

Penny (loafer) for your thoughts? If you’re ready to add preppy styles to your wardrobe, take your style quiz and order a Fix. An expert stylist will hand-select preppy pieces based on your unique style, fit and price preferences. Or, head over to Stitch Fix Freestyle™ to instantly buy items suited for your style and size. Either way, shipping, returns and exchanges are always free.

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