The Guide To Preppy & Ivy League Style | Wardrobe Curation: Women/Menswear

In fashion, preppy style and the Ivy look denote an aesthetic based on a grand history that is visually conveyed through understated, neat, and well-made clothing giving a look of mastered relaxed confidence and a laid-back scholarly type of sophistication. The restrained opulence offers the nature of luxury but not so overtly which suggests that the wearer is educated, refined, and garners a form of conscious prosperity along with an aura of timelessness due to the origins of this style. The Ivy look in regards to fashion exerts maturity and intelligence without speaking a word due to its scholarly and deluxe essence, while the prep look gives a  lively lavish essence that is fresh, yet classic and everlasting.

The term of preppy originates from private, university-preparatory schools and is commonly associated with the subculture that has a nature of vocabulary, speech patterns, etiquette, and dress to reflect their athletic and academic traditionally upper-class lifestyle, but this overtime has altered to create the modern preppy and ivy looks we have today unless you feel aligned with the traditional take of the fashion to signify the affluence the style arised from. 

Though prep and Ivy League looks to go hand in hand, the difference between the two is found in essence and origin. The Ivy League look tends to be more elegant and cultivated, with quieter confidence for the academically oriented wearer which developed further in 1910. This style provoked a sense of community amongst students who came from similar backgrounds and allowed them to distinguish themselves visually. The Ivy style began to grow in establishment through university culture and life then held great influence within the 1950s. Prestigious students wanted formal clothing that was elegant, but still well suited to casual situations as Ivy League schools and neighboring communities.  As the Ivy look became further spread, the preppy style, which is recognized for clean, polished, and colorful leniency emerged inspired by nautical roots. 

Location is also a defining factor of how the preppy style will be sported. For example, the Southern prep style generally contains bold pastels, nautical or athletically aligned themes, and garments of lighter materials due to a warmer climate while a New England prep will feature more understated muted hues with darker overall looks derived from equestrian or country club culture. Both derive meanings from Harvard, Princeton, and Yale as they were most noted to breathe life into the clothing subculture. By the 80s, many brands produced garments that combined both prep and Ivy League essences into one, gradually intertwining the two counterparts into the style that we tend to see today. The most present separation is the varying degrees of formality and semantics of the look. 

Brands such as J. Press and Brooks Brothers developed products earlier on that many drew inspiration from and to cater to the original demographics that allowed for them to go from a prestigious academic setting to traditional leisurely usually athletic or social pastimes, and rowing. Sportswear grew to be more common following WWI, which symbolized strength and leadership among male students, themes that are very present in these looks. 

Over the years, preppy fashion expanded past its Northeastern preparatory school roots and was adopted by a more widespread community with many backgrounds. The stylization of prep style continued to grow throughout the twentieth century and was adopted into mainstream media such as films, magazines, etc which inspired many to take style cues. 

Crucial aspects of this style that are upheld in any application are attention to detail, conservatism, layerings, androgynous variables, and most importantly a specific type of branding. 

Brooks Brothers is the oldest clothing retailer in the US, headquartered in Manhattan and founded in 1818. Originally focused on menswear, they created the prominence of the Ivy League look in the early 1900s and still produce to this day The brand defined American style out of innovation, quality, value, and very specific traditions along with core values that introduced garments such as the original button-down polo shirt, being the first to offer madras, democratizing the repp tie, and introducing pieces such as the shetland sweater to America- just to name a few feats achieved. The brand dressed many cultural moments and shaped many wardrobes.

Ivy and preppy looks were becoming the visual narration of many cultural events. Experiencing many revivals as well, from the early 1900s to the 50s, 80s, and again in the early 2000s with an updated “prepdom” look- pieces that are primarily youth-oriented in addition to the classic offerings.

High fashion brands have contributed to building this aesthetic and defining the codes of dress to be utilized. One of the most prominent is Ralph Lauren who paved the way for what we recognize today as classic, traditional American style. The brand is synonymous with the Ivy or Prep style. Ralph Lauren at its core has a focus on lifestyle the Ralph Lauren Corporation offers diffusion brands with differing aesthetics, themes, and price points  Polo Ralph Lauren, for example, has a great emphasis on sports which fulfills the athletic component of this aesthetic.

Another brand that has contributed to establishing this look is in the 1970s, he began designing preppy clothing for his own eponymous menswear line in the 1980s. At this point in time, the prep look was beginning to experience a revival as vibrant trends were beginning to cycle out. and Tommy Hilfiger became one of the most prominent brands in 1990s sportswear with a distinctive prep-conscious lenient that had an interchangeable purpose, but always focusing on luxury in these moments even with wearable “casual” clothing and personal style.

Working with an aesthetic for personal style can mean working with setting the foundation of your look, pulling inspiration, or working with specific variables to integrate into or mix into other styles.

Now, it is quite common to interpret the Ivy League style in a manner that utilizes other languages of dress or pushes boundaries but keeps the classic, clean, and proper look intact. This creates the mastered relaxed confidence and laid-back sophistication that produces an elevated Ivy League or prep look.

This aesthetic is built from structured silhouettes with relaxed components, strong staple garments, and subtle or elegant branding typically found in the form of embroidery. The Ivy League look possesses a color scheme that practices restraint, sophistication, and purpose based on neutrals and deep rich primary colors such as red, emerald, and navy.

Preppy styles will incorporate more color but will not be too saturated, the colors must harmonize and create a streamlined, seamless, put-together look. These colors are often variations of hues inspired by a lifestyle so shades of blue, reds, and modest, elegant pastels. Patterns such as stripes, plaids, Windowpane, tartan, and nautical-themed patterns are the most common to be integrated in balance with your look.

Now we will do a rundown of the traditional garments needed to achieve this aesthetic. This approach to fashion has a focus on curating a specific image, but the image needs to be liveable and comply with lifestyle. As designer Lily Pulitzer states, “Style isn’t just about what you wear, it’s about how you live.”

 The first garment we will be going over is the staple Oxford shirt. Though categorized as a dress shirt, the oxford is not always deemed appropriate for formal situations and the dress shirt is far too much for everyday wear. The Oxford is made of a thicker material and almost always will feature a standard basketweave along with a button-down collar which makes the shirt durable and strong for where the day takes you.

Another staple is the blazer, typically this is a piece utilized more for an Ivy look and a more formal prep look. The navy blazer is conventional for this aesthetic and originates from officer uniforms of the Royal Navy. The piece has a great range of versatility and styling options on the spectrum of casual to formal events. The cut of the blazer should feature a natural shoulder, and rather than visible darts that produce a closer fit to the body, a sack cut should be worn to allow for the blazer to drape. This gives space to layer if this is an area of interest or needed for function. Double-breasted blazers for nautical tributes work well, but usually, a single-breasted blazer is opted for with a center vent.

Another option is a trench or topcoat opposed to the water-based origin, this piece has a land-based history relating to the clothing of sportsmen in the English countryside in regards to this style. This coat may be unconstructed for a relaxed soft silhouette or sharper structure, either way, tailoring, fit, and precision is a must as this will either pull the look together or create disturbances in proportions.

The next piece is the cable sweater which is associated more with East Coast preps. Though many think of the nonchalant drape slung over the shoulders in regard to prep, this is a piece that can bring in different essences based on the design. The signature version of a sweater for this style is typically in a slim fit that can be worked seamlessly in and out of looks for both day or nightwear.

If you are less interested in the soft academic take on this look and want a more athletic, strong, or laid-back approach a varsity jacket or rugby jersey can be worn to channel a sportswear vibe to give a preppy yet sporty sensibility that does not give a pure athletic look. Instead, this gives a rough and tumble aura due to its heritage to transform a look or add further essence.

Trousers, denim, and skirts should remain streamlined and fitted to suit body type and occasion. Neutral tones, white, black, and medium to dark blues. It’s best to opt for soft denim that is achieved in character through authentic ring-spun construction and chinos should be fitted in a relaxed streamlined way. Too tight is dated, too loose isn’t modern, this applies to chino shorts as well as to serve as a staple to wear as they are lightweight and woven in a twill weave to provide a garment that has ease in wear, but is clean to the eye.

The polo shirt is the epitome of preppy style that comes in a range of fits crafted from the archival polo sport design. the polo was a contemporary button-down sports shirt and was distinguished by rugged materials featuring a button-down in order to secure the collar to the body while riding on horseback or creating drastic movements through the torso into the arms. This captures preppy fashion well- the elevated athleticism channeled into an intellectual proper take on living life. The polo shirt is a simple way to integrate in accents of expression for your personal style through design.

Loafers, boots, and sneakers work well for this style. Boat shoes are reserved for more casual events and spring or summer. Boots typically will either be in a clean simple design or equestrian types such as riding boots. The loafer relates to coastal culture with a variety of lenients in regard to categories for design. Traditionally they are casual options that many wear for a relaxed dress code or more formal events, but not black tie. Occasionally adornments such as detailing, decorations, or tassels will be featured. This must be done in equilibrium with the essence of your look. A classic heel should have a sleek, delicate silhouette or be very sturdy and durable yet graceful since the ivy and prep look is typically quite androgynous now this is a way to garner a more feminine take.

When it comes to accessorizing, there should not be many statements made without a specific purpose. A prep or ivy look needs accessories such as fine jewelry, timepieces, ties, hats, purses, bags, sunglasses etc to pull the look together, but over-accessing will overpower the classic pieces. Though this aesthetic comes from an affluent origin, displays of wealth should not be a priority.  The goal is to unify and practice restraint but to know which boundaries to push in order to express oneself without crossing the line out of the visuals or intent of the aesthetic. 

The last point I want to make about this style is an attitude, the conceptual values of this aesthetic are principled, public-spirited, humble, and mindful. For a true prep or Ivy League look, this is found in understated, classic, timeless, and elegant clothing that is worn its full lifespan as there is a respect for strong craftsmanship and design. This aesthetic contributes a dedication for both the mind and body, to live in a manner that is respectful to oneself as well as others, and upholding a style that allows you to live in a way that moves forward and have your clothing serve you so that you may focus on what life has to offer. As the mission statement of Ralph Lauren goes, “to inspire the dream of a better life through authenticity and timeless style.”


SOURCES: History, Subculture, and Sociology of Prep/Preppies – https://haenfler.sites.grinnell.edu/prep-preppies/ The Preppy Clothes and Brands You Need In Your Wardrobe- https://www.fashionbeans.com/article/preppy-clothes-brands-style-guide/ Brooks Brothers- https://www.brooksbrothers.com/about-us/about-us,default,pg.html Ralph Lauren Information- https://corporate.ralphlauren.com/ Preppy or Ivy League?- https://tbphelps.com/blog/are-you-a-preppy-or-ivy-league-style.html Ralph Lauren imagery by photographer Arnaldo Anaya-Lucca: https://www.instagram.com/arnaldoanaya