Men’s preppy style: Mastering timeless wardrobe essentials

Two men with preppy outfits walk at a beach.

Men’s preppy style: You may certainly associate a man wearing some navy sports coat or some funny-looking argyle socks but it is far more than that. But how to dress preppy as a man?

The men’s preppy style is about expressing elitism and combining it with casual clothing. Most of the time preppy men’s fashion is about mixing something casual with something formal. Combining vibrant patterns and classic coloured cable knit sweaters is one way to look like a preppy style men.

Since there is a lot more to the preppy aesthetic for the male side, we will explore it deeper in this article and give you some preppy wardrobe essentials to work with. If you stay to the end, you may get some specific outfit inspiration for your preppy look.

Definition of preppy style

The preppy style refers to a trend that originated in the 1950s and 60s amongst students of the famously known Ivy League universities in the USA.

The expression “preppy” derives from the word “preparatory” and means this form of preparatory school the students mostly attended to prepare for Ivy League universities. 

The preppy aesthetic went through some changes in the 1990s as it was more common to wear relaxed outfits. That was the time when linen and flannel came into play as new fabrics that dominated this style.

This changed in the 2000s though as preppy style went back to its roots. Nowadays, the preppy style consists of a mixture of all periods and is more versatile than ever. 

Essentials for putting together a preppy capsule wardrobe for men

For a capsule wardrobe representing the preppy aesthetic, you will need several garments fitting casual as well as formal events. Luckily, you can dress your prep style up and down easily.

As this style features preppy clothing, we will experience timeless designs as well as elegant yet playful attire. Your preppy capsule wardrobe should consist of about 20 staples of men’s preppy style to give you some varieties when styling. So, let’s take a look at some of the garments representing the preppy style:

Preppy tops for men

  1. Polo shirt: This is the perfect allrounder from formal to casual.
  2. Rugby shirts: Optimally suited for a sportier preppy look.
  3. Button-down shirt: Matches mostly formal occasions.
  4. Oxford shirt: Suits most occasions. Opt for blue, white, or grey.
  1. Elegant sweaters: V-neck, crew neck, or cable knit sweaters are the main choice here.
  2. Blazer: A rowing or navy blazer levels up any outfit imidiately.
  3. Suit: A classic cotton or seersucker suit offer a great fit for formal occasions.
  4. Curdoroy, wax jackets, and wool coats: The perfect overwear for men’s preppy style.
This picture shows an Oxford shirt and a Wool sweater from Ralph Lauren. A perfect combination for winter.

Men’s preppy trousers

The trousers on this list will complement the tops we’ve just featured:

  1. Chinos: The ultimate preppy trousers for any occasion.
  2. Khaki pants: The more formal sibling of the chino.
  1. Dress pants: They offer a unique fit for formal occasions.
  2. Jeans: Perfectly fitted for casual occasions. You can also try shorts.
  3. Linen pants: Perfect for a relaxed and laid-back look.

Preppy shoes for men

One thing that is missing to create a unique preppy style is a nice shoe. This list will feature some of them but if you want to learn more about it, check out my article about preppy shoes:

  1. Loafers: The most versatile and matching shoes of men’s preppy style.
  2. Boat shoes: The little brother of the loafer, optimally use on a…boat.
  3. Oxford shoes: This formal alternative will look great on any man.
  4. Elegant sneakers: An elegant sneaker is a versatile shoe for almost any occasion.
  5. Boots: A variety of boots suits the preppy aesthetic.

For more inspiration, check out my article about preppy shoes.

This picture shows a pair of elegant sneakers from Ralph Lauren.

How to achieve the perfect men’s preppy style

The following paragraphs will highlight some of the most common trademarks of the preppy style to follow in order to achieve the perfect preppy aesthetic.

Opt for neutral colors and patterns

The preppy style features some unique patterns and colors. They will express sophistication and elitism paired with the breaking of old traditions and rules. Some of the colors you will associate the preppy style with, are:

  • Beige
  • Khaki
  • Navy blue
  • Olive green
  • White
  • Burgundy
  • Pastel colors such as lime green, pink, baby blue, yellow
  • Forrest green

These colors represent the preppy style the most and you can find them in many preppy outfits. Along with some unique patterns, they create a beautiful mixture. These patterns are:

  • Check
  • Stripes
  • Plaid
  • Plain
  • Animal prints
  • Collegiate stripes

The combination of colors and patterns will create a great contrast.

Embrace natural fabrics

The different fabrics prep uses are not only meant to create a contrast but are also suited for different occasions. This list will show you what fabrics prep uses:

  • Wool
  • Tweed
  • Cotton
  • Cashmere
  • Linen

Mix and match classic fits

When dressing preppy, you will need to keep an eye on the fit. One of them is the tailored fit. This fit is tailored to the body and was popular in the early days of preppy style. Especially if you have a great body and like to work out a lot, this fit will suit you. 

Another rather common fit is the classic cut. Straight-cut jeans and other clothing represent this fit. You will find it on many items of clothing, like chino pants and jackets.

If it is colder outside or you just want to have many options, layering is something that is not only practical but will also look great.

Finish with preppy style accessories

There aren’t many accessories, preppy men wear. This small collection of accessories will complement the outfits perfectly though. Starting, watches are a key accessory when it comes to being formal or on a casual occasion. You can find a guide to choose the perfect timeless watch here.

Also, caps can be found to be quite popular, especially when it comes to activities like golf or tennis. I would recommend wearing white ones as they will look the best and won’t heat up in the sun.

Another accessory is a necklace. To represent the WASP aesthetic, a cross will be a great option for a necklace. Lastly, if you are a member of an Ivy League university, cufflinks with the logo will be a great option to put on your suit. Paired with a graduate ring this will make you the ultimate academic prep.

For formal occasions, you will want to wear a necktie and a pocket square, preferably with the pattern of your university. 

To represent the nautical flair, preppy style often strives for, try adding a ribbon belt to your capsule wardrobe. This accessory is a key piece for a true prep. 

For an in-depth guide on preppy accessories, check out this article.

Preppy watch with leather strap.

Best preppy clothing brands

As we are now ready to put together our preppy looks, lets have a look at so refined preppy brands you can shop from:

First and foremost, we have Ralph Lauren, a preppy brand unlike any other. With iconic pieces as polo shirts, chinos, and a crewneck sweater, this brand is one of the best preppy clothing brands.

Next up, we have Tommy Hilfiger, a preppy brand know for having a creative director. Staples for your capsule wardrobe include all kinds of sweaters, khaki pants, and a varsity jacket.

Another iconic brand representing collegiate style is Brooks Brothers. Perfectly suited for representing a modern preppy style, this iconic brand features garments like a navy blazer, a button-down shirt, and loafers.

Regarding those preppy shoes, L.L.Bean is your go-to-store. Featuring multiple preppy shoes as well as the timeless L.L.Bean boot, this brand has a unique charm.

Regarding those preppy accessories, Smarter & Branson is a secret tip. They offer anything from silk ties to hats and caps for you to complement your preppy capsule wardrobe.

Preppy outfits for men

The following paragraph will feature some outfit ideas for men. If you want to get more inspiration, check out my article about 23 preppy outfits for a more detailed list.

Casual preppy outfit

The casual preppy outfit consists of a pair of loafers combined with some neutral-colored trousers and a colorful polo shirt. This style, as the name already tells, perfectly suits casual occasions. You can layer it with a jacket in the winter. 

Additionally, some accessories like sunglasses and a watch will look great on that outfit. 

Cocktail party outfit

The featured outfit consists of a button-down shirt, chinos, and additionally a blazer. Boat shoes will suit this occasion perfectly because of the previously mentioned features. 

This rather formal attire is great to meet new people but still having a good party outfit when the evening becomes a little wilder.

For some more inspiration on preppy workwear, check out this article.

Sporty summer outfit

This outfit will look great for any casual occasion in the summer with your well-off friends. The combination of shorts and a button-down shirt looks great on nearly anyone. A belt is a nice add-on you can wear to create a little contrast. Optimally, this will match your loafers.

Now at last we come to some styling tips to put together any preppy outfit for men.

Final thoughts on men’s preppy style

This article summarized the most important aspects of the men’s preppy style. 

The key factors are matching clothes of good quality and confidence. Also, choosing the right clothing with the right colors and so on can make a huge difference. Additionally, shoes and accessories can complement an outfit but shouldn’t be the focus. 

All in all, men’s preppy style can be summarized by combining something casual with something formal to express your elitism and your elite activities.


What is preppy style for guys?

Preppy style for guys features a clean and put-together look of a polo shirt, a blazer, oxford shirts, some chinos, and loafers.

What are preppy men’s clothes for summer?

For summer, men’s preppy style offers chino shorts, Ralph Lauren Oxford shirts, polo shirts, and linen shirts as well as loafers and boat shoes.

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