If youve been searching for a preppy style guide, youve definitely landed on the right page.
Today, we go into extensive detail deconstructing the preppy aesthetic.
The term preppy refers to a style of dress, but also evokes an entire lifestyle.
Not really the flapper/zoot suit 20s, but the Ivy League, society foundation.
Thats the one wed recommend if youre looking for a true deep dive.
You may even be able to raid your parents or grandparents closets for some of the essentials.
Preppy Shirts
Like so many other styles, that preppy look starts with the essentials.
Think about what youre going to be wearing every day, and build on top of it.
They were originally worn by polo players and actually had button down collars.
(Well talk about this more when we get to oxford shirts.)
They all have a knit collar and cuffed sleeve with a 2-3 button placket.
And, they come in two weaves:jersey(like your t-shirts) andpique.
Pique is a more textured weave and feels thicker than jersey.
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Unrecordedis an Amsterdam-based clothing brand renowned for its less-is-more approach in menswear design.
The rib-knitted hemline and cuffs only add to the preppy twist of the outfit.
This knitted polo shirt does have a slightly wider fit.
So, when in doubt, size down.
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it’s possible for you to find polos everywhere from Walmart to high-end manufacturers.
Polos first became a popular shirt in the 1920s.
The new style was so popular that is went far beyond mere tennis wear.
you’re free to still find the iconic alligator logo on Lacoste shirts.
Since the brands launch in 1972 their polo-playing logo has been a sign of preppy quality.
Luckily there are several other custom t-shirt and polo shirt companies that charge quite a bit less.
Jersey polos have their fans also, partly because the fabric is sleeker and more finished looking.
Henley Shirts
While polos come in long sleeve versions, preppy fans have 2 other options.
Both have their beginnings in British sports.
A Henley is a collarless shirt with a rounded neckline, a 3-5 placket with 2-5 buttons.
They can be made from either pique or jersey knit.
The original henley was favored by university rowing teams in the nineteenth-century.
The name comes from Henley-on-the-Thames, the host of the Royal Regatta.
Traditionally, the losing team would give their shirts to the winning team.
This is why a buttoned front was important.
They are reasonably priced, come in an array of colors, and are a great basic botton layer.
As the sport took off and clubs formed, teams started wearing the same shirts to show their unity.
Originally made of wool, heavy cotton soon became the standard.
Rugby shirts are generally colorful, frequently striped, and have a contrasting collar.
While the body is a knit fabric, the collar is most often a woven cotton.
Crew, Rowing Blazers, Hackett, Gucci, and Thom Browne.
you’re free to find everyone from Prince Harry to Snoop Dogg wearing them.
A great movie reference for rugby shirts is Michael inThe Blind Side.
It even shows how preppy crosses into street culture.
Oxford Button-down Shirts
Button-down shirts are another clothing item with its origins in England.
Men playing polo found that their collars would flap-up during play.
To avoid the interfering and annoying they started using buttons to hold the collars down.
John E. Brooks, one of the founders ofBrooks Brothersbrought the style back to the United States.
The basketweave fabric became a standard for dress shirts.
They present a clean look.
60 years later, President Kennedy popularized pairing the button down with his suits and ties.
This brought the Ivy League look to the masses and further cemented the look as an American classic.
But of course, button-downs arent just for Oxford cloth.
These make great additions to your wardrobe because of their versatility.
For a complete button-down collar breakdown visit ourguide.
Cable Knit Sweaters
The classic cable knit sweater is a great wardrobe essential.
Thecable patternadds interest, but isnt necessary for your sweaters.
Just a plain wool in either crew or v-neck is a great addition to any wardrobe.
Again, you might find these from just about any brand and in any material.
Be careful purchasing lower priced sweaters because they may be coarse, inferior quality cashmere made in sweatshops.
A bit a research will find you a quality garment you’re able to afford.
This is another import from the British Isles; the Aran Islands are off the west coast of Ireland.
These sweaters use a combination of knit stitches such as cable, moss, zig-zag, diamond, etc.
to create patterns in wool.
Originally, fine merino wool in its more natural state was used.
It was undyed and retained its natural oils and lanolin making the sweaters water-resistant.
The patterns were individualized so a familys history as fishermen or farmers could be read in the wool.
For more on Aran sweaters, stitch meanings, and where to find authentic Irish Aran sweaters seethis guide.
In fact, Chris Evans spent most of his time in the movie Knives Out in an Aran Sweater.
Youll also find these sweaters in vest andcardigan form.
Fair Isle was popularized by HRH Edward, Prince of Wales in the 1920.
Bean, Brooks Brothers, J Crew, or Lands End.
Fair Isle has also been embraced by couture designers like Chanel and Karl Lagerfeld.
Fair Isle, while always a classic, transcends that to become more of a trend or fad periodically.
In fact, 2023 is one of those times.
This is another preppy fashion that has been embraced by streetwear designers.
Companies that are transforming fair isle areLoewe, Bowden, and Junya Watanabe.
Argyle Sweaters
Weve gone from knit creating the pattern to patterned color.
The happy median for many preppy dressers may be argyle.
This is another post-World War I British import made popular by the Duke of Windsor.
If you want the original argyle, shop at Pringle of Scotland.
Youll often see argyle sweater vests.
This is a great, classic look, even under a sport coat.
It adds a pop of color and pattern without being too bold.
Argyle can transform from strictly preppy and traditional to street smart and bold.
Sportcoats and Outerwear
Youve got your shirt, sweater, or vest on.
Now you need something to keep you warm and finish the top half of your outfit.
You wantstyle and warmth.
With preppy style you have a few options that are classics.
All can be found at numerous sources in the full price range from reasonable to extravagant.
(Some people mere make the distinction based on buttons.
Blazers have metallic and sportcoats have horn.)
The navy blazer has itsoriginsin British history.
This, of course evolved into civilian wear with longer, single- or double-breasted flannel jackets.
Today, they also come with either the iconic brass buttons or horn buttons.
This is a great look that can be dressed up or down.
In fact, there is very little that wont work with one.
Dont worry about price either there is a blazer in every price category.
Add in a fine watch, the pocket square, and penny loafers and youre ready to go.
Tweed and Plaid Sportcoats
Nothing says British establishment more than tweed and plaid.
You have Scottish tartans, Harris tweed, herringbone and houndstooth.
Tweeds are the original golf cloths of the early 1900s.
Add some elbow patches and long pants and you have the quintessential Ivy League professor.
Of course, pairing the sportcoat with jeans and a Henley gives you a modern look also.
For the ultimate bespoke experience, visitPrickly Thistle.
If you are unsure how to style plaid, visit the Cooliststyle guide.
Camelhair Coats
If navy or tweeds arent your preference, think about a camelhair sportcoat or overcoat.
It is warmer and more durable than wool and such a classic that they are worth the investment.
Though, you could get quality pieces like this one fromJean-Paul Germainat surprisingly affordable prices.
Camelhair polo coats are often found at vintage stores.
In fact, they are often favored by fashionistas.
Preppy pants are slim fitting rather than baggy, and especially not drop crotch (hip hop style).
Look for smooth and elegant.
Traditionally your bottoms would be flat fronted, but dont worry, pleats are perfectly acceptable.
They were made of a thick twill fabric and dyed a khaki color in China.
If you want the real thing, visitBills Khakis.
The company was founded to bring back traditional cavalry twills that were no longer being made.
When it comes to effortlessly preppy pants, ban those red trousers for life.
Earth-toned chinos are the it pants, sophisticated, casual, and with excellent repeat wear potential.
Its hard wearing and warm.
Thus, it is a common material choice for suits, sportcoats, and pants.
Bank, Lands End, and Brooks Brothers are all good sources of everything corduroy.
Beware: there are some extremes in preppy clothing that should be used more in moderation.
For instance, pants with bold embroideries of boats, anchors, or marine life on them.
This is the ultimate in Preppy with a capitol P, but really isnt for most people.
Its also more commonly found on childrens clothing these days where it is perfectly acceptable.
Raw and selvage jeans are a good choice.
Stay away from overly baggy and slouchy plants and you have the foundation of a preppy look.
Preppy Shoes
Weve already discussed preppy argyle and fair isle socks.
But what are you going to put them in?
There are definitely some shoes that are more preppy than others.
Much like the clothing, may have their origins in sporting events.
Both are stylish and can be adapted to suits or jeans.
If youre thinking of pair shorts with dress shoes, go with either penny loafers or deck shoes.
Broguesare made from a number of sturdy pieces of leather that tie up.
They are also sometimes called wingtips.
Oxford shoes have the same basic construction, although the toe piece is straight across.
They often dont have the perforated patterns.
This is a cleaner look.
Most dress shoe manufacturers make brogues and/or oxford shoes.
you’re able to even order them bespoke from a number of companies and cobblers.
There are also differing ideas about the origins of penny loafers.
However, some people attribute the design to Norwegian fishermen.
That is where Bass Shoes came up with the name of their classic loafers Weejun, short for Norwegian.
Their theory is that students traveling to Scandinavia in the early 1900s brought the style back to North America.
The name penny loafer emerged in the 1950s.
It was either a sign of good luck, or having the cost of a phone call on hand.
Sperryis one of the iconic manufacturers of preppy shoes.
Founded in 1935, they have been making their Top Siders for generations of boaters.
Today, the shoes have better structure for street wear, but still retain the original aesthetic.
Other common boat shoe manufacturers include: Dockers, Ralph Lauren, Alden, L.L.
Bean, Lands End, and Columbia.If you need even more inspiration, check outour guide to boat shoes.
Duck Boots
Most of the manufacturers that make boat shoes also make Duck Boots.
They were first created by Leon Leonwood Bean, the founder of L.L.
They were created to keep your feet dry while hunting.
But of course, other classic preppy brands have their own version of the duck boot.
You just need them without the leather and much higher.
Like most things preppy, Wellies have their origins in British culture.
Luckily, Hiram Hutchinson and Charles Goodyear invented a way to vulcanize rubber in 1852 making it waterproof.
When the Dukes design was combined with the new material, the Wellington boot was created.
And, after World War II, Wellies were adopted by gardeners and fishermen.
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Today, Wellies are made in a variety of colors by a variety of manufacturers.
Regardless, they are a part of preppy history.
For women, you’re able to watchMona Lisa Smile.
Its pretty obvious that preppy is everywhere.
To some, it is an ugly throw back to snobbish society.
To others it is the quintessential guide to successful dressing.
So, what do you consider a preppy fashion essential?
Do you have any specific suggestions for preppy mens clothes we didnt mention or feature?
What are your favorite preppy brands?
Leave us a comment below!
