If you had asked me a few years ago what style of fashion I feel a connection with the least, preppy would have been on the list. So it may surprise you, or possibly not, that it is now one that I feel most connected to.
Fashion and personal style is a fun, and sometimes confusing journey.
There is a store in my local mall that I walk by several times a week, and in the window, there is an advertisement for Ralph Lauren.
Every single time I walk past that window I look at the poster and admire it. That is the version of preppy that I want.
Ralph Laurens version.
And now that polo shirts are back, I feel the need to seek one out that has his infamous logo on it, just because.
There has been a shift in what preppy style entails, also known as modern preppy style. But there has also been a shift back to the days of yore.
To the simplicity of the 90s version of classic preppy style.
Remember those J.Crew and the iconic Ralph Lauren advertisements? There are Instagram pages that pay homage to these idyllic eras, and they are some of my favourite follows for inspiration.
But first let us delve into the history of preppy style.
A 12 Piece Preppy Spring Capsule Wardrobe
Striped Polo | Jeans | Glasses | Tote | Headband | Earrings | Trench | Mesh Ballet Flats | Blazer | Socks | Loafers | Black Handbag | Skirt | Cable Knit Sweater | Tank Top | Animal Print Bag | Red Zip Sweater | Navy Blue Trousers | Button Up | Boat Shoes | Kitten Heels | Hair Bow | Red Clutch | Sunglasses | Tan Pants | Black Cardigan | Sneakers
What is Preppy Style?
The notable story of preppy style. A sartorial symphony that plays to the history of fashion with its crisp collars, nautical nuances, and an aristocratic air that whispers of old money and ivy-clad walls.
Maybe not so much whispers, as yells loudly.
Can I just say that I love the word sartorial? I try to plug it into my life whenever possible, but I don’t get to say it as much as I like in my day-to-day life.
Far from being a mere trend, preppy style emerges as a cultural phenomenon, that is woven into the American narrative through elements of elitism, academia, and a vibrant youthful energy.
When I think of preppy my mind jumps to Blaine from Pretty in Pink. He just has that stereotypical preppy douche vibe that we all know and love. Or don’t love.
This style is like a symbol of a certain socioeconomic class and educational background, and it transcends its aesthetic appeal, reflecting deeper societal values and aspirations.
Primarily the classic preppy style was for men, but as it evolved there became a very strong focus on preppy style for women.
The dawn of the 20th century witnessed the refinement of this style, deeply influenced by the leisure pursuits favoured by the American aristocracy—namely yachting, polo, tennis, and golf.
Each of these sports contributed distinctively to the evolution of the preppy aesthetic, interweaving their respective sartorial elements into the fabric of this long-lasting fashion statement.
As a non-participatory, sports-adverse person, I will just pretend.
The 1950s stand out as a golden era, when preppy style broke from the confines of the elite and into the broader public consciousness.
This was thanks in part to icons like Grace Kelly and Jacqueline Kennedy, who donned the preppy mantle with an elegance that was both enviable and attainable and it drew the focus more towards women.
The pages of “The Official Preppy Handbook” in the 1980s analyze this style, transforming it from mere clothing to a guide, a lifestyle steeped in a mix of nonchalance and meticulous grooming.
Should we start a book club and read this?
Into the 21st century preppy style, ever the chameleon, adapts, evolves, yet steadfastly clings to its core of crisp lines, conservative hues, and an air of perfected carelessness.
But it flirts a little bit with rebellion, to incorporate elements of punk, grunge, and streetwear. And even so, it always returns to its roots, like a prodigal son.
It is a testament to the enduring appeal of a well-curated, timeless wardrobe that balances formality with a sense of leisure and approachability.
It is a style that boasts of summers in Nantucket, of sailing on the Cape, yet also finds a home in the urban jungle, where it becomes a look that is as comfortable in a downtown cafe as it is on a polo field.
I feel drawn to it because it reflects a love for timeless pieces that blend comfort with a hint of sophistication.
Imagine pulling on your favourite chinos and a crisp button-down shirt, ready for a day that could effortlessly transition from a casual brunch to an impromptu visit to a yacht club or tennis match.
I say “can you imagine” in a very tongue-in-cheek way, because no most of us can’t imagine that life, but we have seen what it looks like.
Anyway, this style speaks to those who appreciate a clean, polished look that carries a bit of history, that may evoke memories of sunny days spent supporting friends at a college rowing event.
Fun fact: I went to school in a university city that was renowned for its rowing.
No one dressed like this though because it was a very non-collegiate, non-upscale city, so we all pretty much looked like we rolled home from the bar and got up and carried on with our day.
Which we often did.
Back to prep though. It’s about choosing outfits that feel natural, garments that resonate with personal stories and experiences, rather than just following trends.
Although prep has become trendy over the years, there is always a hint of it reflected in shows.
Recently I have noticed there has been a stronger presence in this type of clothes, and you are going to see a lot more preppy-style clothing and collegiate-inspired outfits making an appearance.
The polos, rugby stripes, chinos, sweaters over shoulders (or my favourite diagonal across the chest way), sports socks and sneakers, and pleated skirts of varying lengths.
The list goes on, but you are going to notice the nuanced changes. A more relaxed fit, edgier touches, and a lot of masculine vibes in women’s wear.
So, like I noted above, it has a more modern preppy look. It can’t really be avoided, everything comes back and when it does, it is changed even though it will still be the same at its core.
Preppy style, in its essence, is about creating a wardrobe that feels both familiar and effortlessly elegant, a perfect companion to life’s simple pleasures.
How to Dress Like a Prep
The quintessential preppy outfit might start with a pair of well-fitted chinos or a classic, pleated skirt, suggesting a balance between casual ease and a hint of formality.
The tops are often where the preppy style truly comes to life: think polo shirts in varying colours, crisp white button-downs, or nautical-striped sweaters, all suggesting a day spent at sea or a leisurely afternoon on the golf course.
Layering plays a key role in preppy fashion, with items like cable knit sweaters draped over the shoulders,
V-neck sweaters paired with collared shirts peeking underneath, and blazers adding a sophisticated touch to any outfit.
These layers not only add to the visual appeal but also speak to the preppy style’s adaptability to different climates and settings.
Accessories are the cherries on top of the preppy ensemble.
Pearls, whether in the form of earrings or necklaces, add a touch of timeless elegance.
Leather belts cinch in at the waist to define silhouettes, and headbands or ribbon ties in the hair echo a youthful, scholarly charm.
Footwear such as loafers, boat shoes, or clean, white tennis sneakers further cement the preppy vibe, blending functionality with fashion.
I also want to mention that I have seen a resurgence of boat shoes. Yes, you heard me right. Boat shoes have been spotted on the horizon.
Do what you may with that bit of information. I need to marinate in it to see how I feel about this, but in the meantime, I included a pair that I found at Zara.
And you know once it hits Zara, it is starting to make rounds.
What makes preppy style continuously appealing is its blend of tradition with a hint of playfulness.
It’s both an homage to an idyllic, Americana past and a celebration of the timeless, embracing quality over quantity.
For women, preppy fashion is not just about dressing up for the moment; it’s about curating a wardrobe that feels familiar and effortlessly chic, a testament to a lifestyle that values heritage, education, and a certain joie de vivre.
Preppy style stands as a testament to enduring traditions, a celebration of refined luxury, and a symbol of a past era that continues to influence the fashion landscape profoundly.
It represents more than attire; it embodies a rich history, a living legacy articulated through every meticulously buttoned blazer, each neatly striped tie, and the shine of every well-polished loafer.
Note: Get yourself a tie. You won’t regret it.
The narrative of preppy style is like a dialogue between elegance and education, harmoniously intertwined.
But this time, let’s take the traditional preppy look and make it a little more rough around the edges, okay?
Casual Preppy Outfits for Women
Striped Polo | Jeans | Glasses | Tote | Headband | Earrings | Trench | Mesh Ballet Flats | Blazer | Socks | Loafers | Black Handbag | Skirt | Cable Knit Sweater | Tank Top | Animal Print Bag | Red Zip Sweater | Navy Blue Trousers | Button Up | Boat Shoes | Kitten Heels | Hair Bow | Red Clutch | Sunglasses | Tan Pants | Black Cardigan | Sneakers
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