Great Preppy Look For Guys

What is the best preppy look for guys this year!  Pretty much the same as it was 20 years ago, because the best preppy look for guys never changes.

Clothing trends change all the time, but a classic preppy look will always look great – because it is clean, functional, classic, and fun loving all year long.

To understand the preppy look for guys, you have to appreciate the preppy lifestyle and the history of how the style came to be.  The clothing really fits the lifestyle and the things preppies  love to do. 

Best Preppy Look for Guys

History of the Preppy Style

The initial preppy style (or Ivy Style) really started in the mid-1940s.  It was Brooks Brothers and J.Press that started the trend by providing their clothing and style directly to the students on campus.  This shopping convenience started the preppy trend one Ivy League college at a time.

The clothing focused around the traditional New England activities that the students liked to do.  It focused on things like sailing, fencing, rowing, golf, and polo to name a few.

The clothing was designed to be functional for their preppy lifestyle

Over time, designers started creating these styles in brighter colors to capture the vacation habits of these upper class travelers and merged the classic style with the bright, nautical themed clothes we see today.

The clothing had a smart feel to it, but also tied in the Summer activities that were part of the upper class lifestyle.  The small things like button down colors and non-slip shoes created a functional, smart, activities focused style that is still popular today.

The Preppy Lifestyle

The preppy lifestyle was commonly considered the lifestyle of old money families.  These social circles had a defined manner of speech, vocabulary, dress, etiquette, and manners that clearly separated them from the rest of society.

These preppy traits are still true today, but with one critical trait missing.  Money.

The preppy lifestyle no longer requires wealth.  The preppy lifestyle is all about living well in a conservative manor.  Fancy cars, large houses, and expensive accessories, are not part of the modern preppy lifestyle anymore.

Modern preppies are defined by quality of their possessions, not the quantity or cost of them.

The average preppy family is all about spending quality family time doing simple, fun loving things together.  Walks along the beach or boardwalk, playing golf or going sailing with friends, and eating healthy meals at home.

Most preppies are drawn to water activities.  I cannot explain it, but there is a strong passion for all things nautical.  If you feel it too and like the classic preppy style, then face it,  you are a preppy too and need to embrace it.

Just don’t worry about the crazy colors.  They are not required!

Preppy Brands

There is a lot of confusion about the value of wearing these high-end preppy brands.  Not to worry, you can wear any brand you like.

The key to the preppy look for guys is high quality clothes in classic styling.  The colors are often brighter then normal, and often carry a nautical theme or another theme that is common to the preppy lifestyle.

Quality, well made clothes is 90% of the preppy look and all that really matters. 

I happen to believe that the standard preppy brands are worth their cost because they will outlast their cheaper cousins many times over making them the better value in the end.

Let me say that again.

True preppies focus on these brands because of the quality and styling of the clothing.  Better clothing costs more, but also last much longer, and therefore less expensive in the long run.

Don’t take my word for it.  Research it yourself and decide.  Here is a list of just a few popular preppy brands you can try on and judge for yourself.

My closet is about 50% Vineyard Vines and 20% Ralph Lauren.  The rest are other brands I have found over the years and fit me really well.

The fit combined with great quality are the keys to looking great, and should be the primary factor in choosing the brand you want to wear.

Each brand will cut their clothing a little different.  I personally find that the Vineyard Vines cut fits my body type better then all the other brands.  The Ralph Lauren cut has a similar fit but slightly longer and wider.

The lesson here is to find a brand that has a cut that works well with your body and once you find it, you can buy several different items in a few different colors and patterns.

It is much better to find brands that fit off the rack.  I find this to be true with the higher end brands so I don’t mind spending more up front as it saves me money on the tailoring and reduces the total cost of ownership.

The Basic Preppy Look for Guys

The basic preppy look for guys can be accomplished with just a few articles of clothing.  Since we are just talking about a pair of chinos, a button down shirt, and shoes, buying quality name brands is the way to go.

Take a trip to the mall and try on all the shirts from the brands above and be very critical with the fit.  Each company makes their clothing in several different cuts to try them all on.

Also, read the tags and learn how each fabric fits your body.  Different fabrics will wear, look, and stretch differently.  Move around, get other opinions, and then put it back on the rack.  After a few weeks of trying on different brands and styles, you will know what you like and then it will be time to buy.

Best Preppy Look for Guys – Colorful Button-down Shirts!

Button Down Shirt

The button down shirt is the starting point for the preppy guy.  These can be warn to the beach, a family BBQ, the office, and basically anywhere else you can think of.

White or light blue are the best colors to start, in an oxford style, and button down collars.  It is the most versatile and can be easily dressed up or down.

Only buy long sleeve button-down shirts as the short sleeves look silly.  The only shirt that should come in a short sleeve are polo’s and Hawaiian shirts.

Next move into different colors and patterns.  Below are the standards and very common among us preppies.

  • Gingham
  • Madras
  • Seersucker
  • Checks
  • Mini Window Checks
  • Stripes
  • Chambray

Polo Shirt

The polo shirt is the dressier cousin to the tee shirt and a staple in every preppy mans closet.  No great preppy look for guys would be complete without some.

This is where I differ a little with the normal preppy wardrobe.  I love the polo for sure, but I am not that crazy about all the colors.  They are often too hard to match right.

I recommend the polo in subdued colors; white, black, navy, blue, red, and gray.

If you happen to have a very large closet, then feel free to grab the bright colors and different patterns.  Just know that you will not get as much wear from them given they are rememberable and bold.

Fit is always key.  Know your body and where your stretch points are and make sure to get a shirt that flatters it best.

I like to pay special attention to the collars.  Most cheap polo shorts will start curling in the collars or get quickly deformed. 

If you take a look at the high end shirts on ebay or in a thrift store, you will see even after years of washes and wear, they are still in great shape, and the collars are holding their shape.  These are the signs of a great shirt and something you need to look for when buying one.


I personally go between my chinos and dark jeans all the time.  I get my chinos in all the standard colors (beige, green, navy, black, gray) but I wear my beige 95% of the time.

The best preppy look for guys will always have a well fitting, beige or tan chino, in a slim fit with a good amount of stretch in the fabric.

I have found the best chinos for me at the Gap and buy them for around $20/$30 a pair.

I love my Gap pants and can easily recommend them to everyone.  Just one note, you must go into the stores and try them on.  The Gap is famous for their “vanity sizing” and the pants will be labeled several sized smaller then they actually are (so you feel better buying them).

Make sure they fit before you leave the store.

Also, I happen to also fit the Gap jeans better then any other brand so I pretty much do all my pants shopping there.

Best Preppy Look for Guys - Gap Chinos
Best Preppy Look for Guys – Gap Chinos

Boat Shoes and Duck Boots

Preppy guys wear boat shoes pretty much everywhere they go.  If they need to dress things up a bit, they will switch into a good pair of loafers, but the boat shoe is always preferred.

The boat shoe is never worn with socks in the Summer.  When the weather gets colder, most guys switch over to their LL Bean Duck Boots.

I personally do wear “no show’ socks with my boat shoes but never if I am going somewhere near the water.

If I am wearing by ducks, then I opt for a great pair of warm socks in wool.  Sometimes cotton is OK if they are a quality pair since it very cold here in the North East.

Blazer or Sport Coat

The best preppy look for guys cannot be complete without a jacket.  The navy blazer or sport coat are multi functional and can really add functionality to any outfit.

The jackets are used as outerwear when it gets cooler at night or as a regular coat in the Fall, Winter, or Spring months. 

The blazer is used for more formal occasions while the sport coat for more outdoor activities in the colder months.

In this case, since we are only talking basics, the navy blazer is part of the core wardrobe while the sport coats more of an optional article.

I created a separate article all about wearing blazers and the differences between the sport coat, casual blazer, and traditional blazer. It’s called How to Wear a Mens Casual Blazer wtih Jeans.


The best preppy look for guys will always have these basics articles and will make sure the quality and style are perfect. 

The basics are a well fitting button-down shirt, tan chinos, boat shoes or loafers, and a navy blazer.  For more casual gatherings, you replace the button-down with a polo.

Since these are classics, they will be in style forever, and quality clothes will last, so it will be worth it to buy the best quality you can afford.

In the colder seasons, some preppies move towards the English country clothing style which is traditionally tweed fabrics with leather patches and lots of wool used during the hunt. 

This is a bit different then the classics I list above and will dedicate a separate article for it.  The Fall is really is one of my favorite times of the year due to the English country clothing style and worth a read.

I know I left off my preppy accessories like ties and belts but I assumed these were already available and wanted to keep the list simple.

If you found this article helpful, please consider signing up for my email list.  Also, please leave a comment below about items you have in your core preppy wardrobe. 

Thank you for reading!

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