Guide to Men’s Preppy Style

Written By Bakes

Avid writer on Men's Hair, Grooming, and Lifestyle!

Men’s Preppy Style has always been associated with wealth, class and elegance which is no surprise as to why the Ivy League style came back into the fold!

Outside of ensuring their physical appearance is up to par, men have wanted to communicate their social economic status in subtle ways and preppy style allows this to take place.

From the perfect mix of colours and patterns to the ideal fabrics and cuts, we have laid out everything you need to know about men’s preppy style in one place. 

In this post, you will find all of the information needed to start incorporating preppy clothing into your life and look great while doing it!



What is Mens Preppy Style?


If you’re an old-school man who values quality, timelessness, and comfort above all else, the preppy dress style may be for you. Originating at elite north-eastern U.S. universities like Princeton, Yale, and Harvard during the 1920s and 1930s (hence the term preppy), this style has evolved to become one of the most stylish menswear looks around—even if its origins may surprise you! 

Despite the common perception that prep fashion is strictly conservative, the style ranges from buttoned-up and preppy to outright daring. The classic slacks, sweater and bow tie combination tends to be worn in muted colors but has evolved into more adventurous prints and brighter colors. 

Although the look is traditionally American in origin, men today wear elements of prep almost anywhere they can be found—Asia and Europe mainly. As with all trends, certain items are quintessential while others are just convenient.



Preppy Style in Pop Culture 

carlton banks preppy style

The preppy look wasn’t the first style to have widespread cultural influence. In the 1960’s it was the famous Rat Pack, and in the 1980’s Gordon Gekko from Wall Street popularized a unique look that is still to this day associated with wealth, success, and power. 

More recently, you can find characters like Carlton Banks from The Fresh Prince of Bel-Air showing off his blazer collection consistently. These cultural references helped increase awareness of the look among non-preps which only encouraged its popularity today.  

Pop culture has certainly helped to popularize the preppy style. From the way that Will Smith dressed in Fresh Prince of Bel-Air to the long-running success of Jack Ryan as a character, we’ve seen that there’s an appetite for people who dress this way. 

Brands like Sperry and Lilly Pulitzer have kept their appeal by remaining relevant to pop culture at all times (e.g., it’s not a coincidence you’ll see both companies sponsoring events at places like the Kentucky Derby). 

Because preppy style is constantly being discussed, it makes sense for men to look for ways to make this look work for them—and not just because it will earn them points with celebrities.



Investing in Preppy Fashion

The preppy look is all about conservative fashion, and investing in a good men’s preppy wardrobe can do wonders for your business attire. When it comes to men’s preppy style, there are two things that matter: fit and quality. 

If you invest in quality pieces, you get to wear them for years without worrying about looking outdated. So how should you begin? Let’s leap further into how you can invest in men’s preppy style.

First, if you aren’t sure what colors and fabrics suit you best—and therefore what fabrics might be suitable for a preppy style—consider booking an appointment with a personal stylist (or even ask one of your friends). 

A clothing store associate or friend isn’t always going to know what will suit your personality or body type; they won’t necessarily understand if something works with your complexion or not. 

A professional, however, has seen thousands of people and knows which styles go with which types. Just because they may charge you an hour-long consultation fee doesn’t mean their advice isn’t worth it.  

Second, if you can afford it, invest in quality items that will last. There is a reason why the classic preppy style looks so good: classic clothing will never go out of style. You can invest in a few staple pieces like peacoats and chinos. You can dress depending on your needs—and do so for years to come.



Button-down Shirts

Men's Preppy Style button down shirt

One of the most iconic parts of prep is men’s preppy button-down shirts. These are a significant part of any man’s wardrobe, and you can wear them with your favorite slacks and tie for a complete business look or style them with your favorite khakis for a more laid-back outfit. 

They come in bright, vivid colors like blue, red, and green and soft neutral tones like gray and tan. Of course, if you prefer something understated, that option is available too! There are also many different styles of the shirt- collared or non-collared and short sleeves or long sleeves. 

Choosing a men’s preppy button-down shirt will take some time, but once you find one that suits your style, it will be something that you reach for time and time again! 


Boat Shoes and Loafers

Men's Preppy Style Boat Shoes

Boat shoes and loafers may be staples of prep style, but these casual shoes are versatile enough for just about any occasion. You can’t go wrong with this intuitive style, from formal events to family barbecues. 

Add a bit of preppy elegance by wearing them with socks or shorts. Thanks to their variety of colors and materials, it’s easy for men of all ages and tastes to find shoes that fit their sense of style. 



Blazers and Sports Jackets

Blazers and Sports Jackets

A light, colorful blazer is a must for preppy men. Pair it with chinos or khakis and loafers for a summery look. Opt for heavier fabrics such as tweed, flannel, and corduroy in your preppy attire for fall. 

Sports jackets can also be worn in fall and winter if thick enough to keep you warm. Leave out your sweater vest; button-down shirts will suffice in their place.  



Preppy Style Sweaters

Men's Preppy Style sweaters

One can hardly go wrong with a sweater, and it doesn’t get much better than a sweater for men’s preppy style. There are hundreds of sweaters available in today’s market, ranging from cashmere or merino wool to fine cotton or acrylic blends.

Once you have chosen your sweater fabric, it is time to select patterns and designs. Today there are so many preppy-looking sweaters out there in stores; if you want something truly original, you can even customize one.


Varsity Jackets

Varsity Jackets

A jacket with a sports team logo on it is an excellent staple piece for any man looking to take on a more preppy look. The idea of wearing a varsity jacket comes from the traditional collegiate style, and its usage has since spread beyond college campuses.

Navy blue and gray are popular colors, though they come in many other shades as well. Popular brands include Vineyard Vines, Tommy Hilfiger, Lacoste, Polo Ralph Lauren, Johnston & Murphy, and Burberry.



Polo Shirts

Men's Preppy Style Polo Shirts

An essential part of any men’s preppy wardrobe is, undoubtedly, polo shirts. These are stylish and versatile pieces that can be worn on their own or under a sweater or blazer.

The color scheme is up to you—navy and light blue seem to be popular choices—but remember that white will get dirty easily, so pair it with a dark-colored belt or shoes. The collar should match your shoes, while stripes (horizontal or vertical) add flair.

No one does polo shirts like Ralph Lauren. The iconic label has perfected both short- and long-sleeve versions of its classic collared shirts, which are so preppy they go perfectly with a prep school blazer or a pair of chinos and loafers.

They also make excellent casual wear outside of formal occasions—so don’t be afraid to wear them any day you want your outfit to look effortlessly refined.



Rugby Jersey

Rugby Jersey

The preppy sport collared rugby is a men’s clothing staple. It adds an element of preppy style to any outfit, but be careful not to overdo it. The classic color options are black and white, navy blue and white, or red and white. 

You can also choose a plain jersey for everyday wear and switch up colors when you feel more adventurous. They look good under blazers or button-down shirts with no tie; you could also wear them on their own with dark denim if you don’t have time to dress up.




So, you’ve got a shirt and some shorts. What else? Well, some accessories are a must-have for men who want to sport prep style. Firstly, you need sunglasses—and not just any sunglasses. 

You need aviators (or something in that style). Nothing says classic American preppy like tortoiseshell frames and mirrored lenses, so get yourself a pair if you don’t already have them.

Secondly, you need a watch. There are some great options out there if you don’t have one already. If your budget is large enough, it’s time to invest in a quality Breitling or even Rolex. But if money is tight—you can always go with more affordable watches from stores like Nordstrom Rack or Kohl’s and still look great. 

Lastly, consider getting yourself one of those sleek belts. They look great paired with shorts and a nice crisp button-down shirt. Nevertheless, keep in mind that these are just suggestions for accessories—they aren’t required by all means. Be free to mix and match them as you please without overdoing them. 



The Best Brands for Men’s Preppy Style 

Different brands have high-quality suits and ties that will last you through years of business meetings and interviews. In addition to having quality clothing that comes in a variety of patterns, many of these brands also have dress shirts with unique prints on them that can make your outfit pop while still being conservative enough for a professional setting.

Ralph Lauren, Coach & Tommy Hilfiger are the three main brands known for men’s preppy style. Ralph Lauren has many classic items for every man, including sportswear and accessories essential to the preppy look. 

Coach is best known for its iconic handbags, but their lineup includes numerous stylish pieces ideal for any occasion. Finally, Tommy Hilfiger offers a variety of preppy staples at affordable prices. 

With so many great options available, figuring out what makes these brands stand out can be challenging. The first thing you’ll notice when looking at these brands is that they tend to feature bright colors and basic stripes and checks throughout their collections.



Is Preppy Fashion still in style?

If you were asked what you think of preppy fashion, would you describe it as a polo shirt, a pair of loafers and khakis? Then you haven’t been following fashion trends closely enough. These days, preppy style can take on many forms. If it is true that what goes around comes around, then there should be no doubt that preppy fashion is still in style. 

 Recently, even celebrities have been caught up in preppy fashion. Kendall Jenner is often photographed with her boyfriend wearing shorts and polo shirts. Rachel McAdams was spotted at Wimbledon, rocking a preppy look as well. The list continues for those who want to emulate their celebrity idols but don’t know where to start when it comes to style. 




Too many fashion blogs are guilty of showing us the same old menswear looks. Often, it seems as if designers and brands churn out the same monotonous runway trends season after season. There may be some novelty here and there, but these outfits usually have very little in the way of practical everyday wearability. 

For example, many of these runway looks fall under the I can see myself wearing that on a yacht in Monaco next summer. In contrast, prep style focuses much more heavily on wearability than other men’s styles and looks great whether you’re going for an elegant or urban vibe.



To stay updated on everything happening in men’s style/lifestyle, street culture & music follow @heartafact on Instagram


Leave a Comment