How To Dress Preppy | A Man's Preppy Dress Guide

Posted by Rishi Chullani on

The timeless allure of Preppy Fashion has meant that many a gentleman has opted to go for this classic look often featuring Chino's, Sports Jackets, Loafers or Boat Shoes & A Tie! With this How To Dress Preppy Guide, we hope that you have all the information you need to coordinate pieces in your wardrobe for the ultimate look! 

The time has come. You are ready to shun your dated fashion sense and embrace something new. With aplomb. Dress sensibility that can elevate your sense of style and empower you to come across as a gentleman that has their stuff together. Or even better, as a bold, daring gentleman that isn’t afraid of risk taking. Ironically, this desire to flaunt your penchant for risk will have you dressing very unlike Gordon Gekko. A paradox I know, but wait and see as to how this game plays out.

Out goes Charles Barkley attire. In comes Ryan Gosling – or something to that effect. Preppy it is, you tell yourself in your yoda-esque voice. Yes, you are predicting massive change that will come about as a result of your seismic shift in clothing choice. So how exactly do you go about transitioning towards a preppy wardrobe, or even the occasional preppy ensemble. Follow these guidelines, and hopefully your transition will be smoother than an NBA Player- Kardashian relationship saga.  

History of Preppy Style

History Of Preppy Style

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Preppy fashion emerged in the 1900’s as a popular style amongst Ivy League Students at esteemed institutions such as Harvard, Yale & Princeton. Labels such as Brooks Brothers and J. Press contributed significantly to the rise of this, especially as they had often had stores present on these campuses.

The term prep was derived from private preparatory schools that students hailing from wealthy families often attended. These were highly regarded, and those who attended one often went onto further their education at one of the fabled Ivy-Leagues. In a contemporary sense, however, preppy dress-sense can lend itself to anyone irrespective of their background, with emphasis being placed on the actual style of dress that is emblematic of its name – specifically the quality, cut & style of clothing.

So how does this translate into a look within the formal wear sphere? In a nutshell (before we go into greater detail), this often includes:

Button down oxford / seersucker shirts, a blazer, chinos, a splash of pastel colors thrown in (or more for good measure) and accessories that can elevate your look. Bolder looks can encompass the notoriously famed go to hell pants, with peacocks, frogs and the like on full display, more colorful accessories and all out disdain for stylistic norms. How’s that for some change?

Men's Preppy Style

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Preppy Shirts

The button down oxford shirt remains a quintessential element of preppy style, especially when utilized in a more business casual / formal context. While polo shirts are often reserved for less formal events, the button down oxford will hold you in particularly good standing in a more formal setting.

Historically, the button down oxford shirt was actually devised to stop the collar flapping during tennis matches, allowing for fashion and function to co-exist as one (one can somehow see Roger Federer playing in a buttoned down oxford shirt, but that is a whole other topic). When opting for a button down oxford shirt, try embracing  a pink shirt or something with a bit more of spring season pop in it, such as a light green or lavender shirt.

While a more formal ensemble will necessitate the adoption of a necktie (patterned choices work particularly well, including stripes and polka dot ties), ditching the tie and throwing on a sweater will quickly transform your look into a more casual one. Leaving out the sweater can also work, though through layering, a sweater will definitely add character and depth to your outfit.

As will be discussed below, another option with the sweater and shirt is a knitted tie, which allows you to dress down a more formal ensemble or dress up a casual ensemble, allowing you to use it both ways!

Preppy Look with Knitted Tie and Linen Pocket Square

A knit tie can instantly, along with an oxford shirt and colorful blazer, provide you with a classic, preppy look. Featuring The Dark Knot’s Franklin Checkered Linen Pocket Square.

Preppy Look with Paisley Silk Tie

A stunning preppy look, featuring a striped blue and white shirt, balanced out by a stunning paisley silk tie. The light grey vest adds another layer to this outstanding ensemble. Featuring The Dark Knot’s Amesbury Paisley Brownish Gold Silk Tie.

The Seersucker Shirt

A prep wardrobe staple, seersucker shirts are the ideal go to item when looking for a novel and refreshing look. Made from puckered cotton material, seersucker is a light and breathable material that makes it ideal for spring & summer seasons. Of important note is that seersucker shirts should be tucked in, to preserve the formal, preppy look.

 Preppy Seersucker Shirt

A seersucker shirt is an ideal canvas for prep-ville. Here, this blue seersucker shirt is perfectly balanced with a green striped tie. Courtesy of


A requisite in the aspiring preppy gentleman’s wardrobe, a crew neck or v-neck sweater (appropriate for more formal settings) is a surefire way to firmly plant your ensemble into preppy territory. Both options look fantastic when paired with a button down oxford shirt and tie, as well as a polo shirt (for more casual occasions). The three key fabrics to consider when employing a sweater in your preppy outfit are:

  • Cashmere
  • Wool / Wool – Blend
  • Cotton

Men's Preppy Looks with sweaters

A Sweater look during the fall season is perfect for that preppy summer look! Courtesy of


Almost synonymous with a preppy look, navy blazers are an essential item for your preppy wardrobe. Opt for a single breasted blazer to truly embody the preppy style. Solid navy is the most popular choice, given its high degree of versatility, and is perfect for achieving that smart, nautical feel.

There are a variety of materials to choose from, including poplin and wool (with worsted wool being the most popular given its smooth and lightweight feel).

Please note the difference between a blazer and a sports jacket, so as to ensure that you are maintaining a preppy look that is closer to form:

  • A blazer is typically solid and does not have a pattern to it. Texture in the weave of the fabric is acceptable, but there should be no discernable pattern.
  • Navy blazers typically have metal buttons. This distinguishes it from a sports jacket and demonstrates that you are not wearing a suit jacket with an off color pair of pants.
  • Blazers generally have less structure than a sports jacket, however, they are not an unstructured / soft-shoulder jacket.

While not necessarily a requirement, gold buttons will add a touch of class and prep to your outfits!

Looking to add further panache to your outfit featuring a navy blazer? Opt for a pocket square for that additional flair!

Preppy style featuring a navy blazer

Few items attest to a preppy look like a navy blazer does! Courtesy of


Ties & Accessories Sale | Silk Ties & Men's Accessories Daily Deal



Few things scream preppy like a pair of chinos to accompany that oxford shirt and sweater / navy blazer. Chinos are trousers made from chino, which is a twill fabric made of 100% cotton. Typically, chinos are the trousers of choice, with khakis being your standard hue. This color is versatile and allows you to transition from work to the weekend.

With regards to fit, you want your chinos to fit you in the same manner well fitted suit pants would – tapered and straight leg. Rolling up your pant cuffs is optional!

Chinos Preppy Men's Style

Chinos are the defacto choice for preppy wear! Courtesy of

Go To Hell Pants

Looking for a bold look that shows you’ve basically gone off the rails and have read the New York Times Best Seller ‘The Subtle Art of Not Giving A F*ck’  a hundred times over (as a warm up)? Go To Hell Pants, popularized by ultra preppy men from the north east who have taken up summer time shares in Nantucket, The Hamptons or Florida, feature audacious patterns that have John McEnroe screaming ‘ you cannot be serious!!!’.

What initially started out as bright yellow, green and red trousers have now evolved into pants with loud and audacious patterns. If you are strutting these pants, you better bring your Swag-A-Game.

While Go To Hell Pants will definitely make you stand out in your bolder selection of preppy wear, you can always acknowledge that these pants are a vintage throwback to the 50’s / 60’s. It is important to note that if you are strutting Go To Hell Pants, it is advisable to tone down the rest of your outfit, so as to provide some semblance of balance (yes, it can still be achieved with these audaciously loud pants!).

Go To Hell Preppy Pants


Bold, Pink Go To Hell Pants are well balanced here with a navy polo! Courtesy of

Colorful Socks from The Dark Knot

Preppy Shoes

While the rest of your ensemble is of critical important (duh!), your shoes set the tone for your preppy conversation. Your ideal shoes for a preppy ensemble are your classics: Loafers or Boat Shoes.


Loafers are characterized as laceless, low shoes, with a separate sole. The Penny Loafer, popularized by G.H Bass in 1934, features a distinctive leather strip across the top of the shoe with a diamond shaped cutout. These shoes became incredibly popular amongst prep students in the U.S in the 1950’s, who actually coined the phrase ‘Penny Loafer’.

Penny Loafer Shoes

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Boat Shoes

Your alternative, boat shoes, were created as non-slip shoes for sailing, and are generally made of leather. Boat shoes are typically characterized by mid to dark brown leathers, hand sewn finishing, and typically feature a 360 degree lacing system.

Boat shoes are exclusively worn without socks and are tied together using leather boat shoe laces.

Boat Shoes Preppy Style

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Accompanying your preppy style with colorful and bold accessories is of critical importance. While conventional collegiate style ties, such as the one below, will almost always do the trick, there are alternative ways to spice up your ensembles with patterns that will have you standing out in a positive, counter culture manner.

Navy / Red Regimental Striped Silk Tie

The Dark Knot's Canterbury Regimental Navy / Red Silk Tie is ideal for the preppy man!

Silk Ties | Ties | Neckties | Extra Long Ties | Buy Ties | Shop Ties

Plaid / Madras Ties

Madras Ties, popularized by prepsters in the northeast, are characterized by plaid patterns on cotton fabric. While there is a class of madras products that refers to patchwork, we are referring to woven plaid designs. A Madras Plaid Tie can instantly elevate your preppy outfit and have you really standing out!

Madras Tie Preppy Men's Style

A plaid madras tie will instantly elevate your preppy aesthetic! Courtesy of

Animal Print Silk Ties

In line with the notion of injecting color into your ensembles, these unique printed silk ties often feature repeating animal motifs, such as sea life, birds or even chicks. Similar silk ties that feature repeating motif prints include lifestyle ties (e.g golf balls, tennis racquets, palm trees). These unique neckties are instant conversation starters, given that they appear as a splash of colors from afar, but upon closer inspection, often reveal something about the wearer’s interests / hobbies.

Feel free to view The Dark Knot’s extensive range of Animal Print Silk Ties.

Animal Print Silk Ties

Knit Ties

Knit ties, which have made a renaissance in recent years, are ideal for adding textural variation to your attire, and can really elevate your preppy look! They can be used to dress up a less formal look (e.g with a sweater) or to dress down a more formal look.

Feel free to view The Dark Knot's range of Silk Knit Ties.

Brown & Red Striped Knit Tie

The Dark Knot's Rhinebeck Stripes Knitted Silk Tie is the perfect accessory to this preppy look.

Silk Knit Ties | Knit Ties | Knitted Ties | Buy Knit Ties | Shop Knit Ties

Pocket Squares

If you are looking to provide your attire with that final complementary piece that will have you looking like Justin Timberlake’s right hand man, and hence, the ideally dressed prepster, a paisley or floral pocket square will undoubtedly add to your overall look.

Feel free to view The Dark Knot's extensive range of Silk & Linen Pocket Squares.

Preppy Men's Look


Pocket Squares from The Dark Knot

And that's a wrap for this one! I hope that you have enjoyed reading this as much as I did writing it!

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