A 12 Piece Preppy Winter Capsule Wardrobe

A white background with 12 clothing items plus shoes and accessories for A Preppy Winter capsule wardrobe. In the middle is a black box with white text that reads, "A 12 Piece Preppy Winter Capsule Wardrobe."

A few months ago, when I was discussing preppy capsule wardrobes, I mentioned that preppy style was making a comeback. And lo and behold, what do we see at the Miu Miu S/S 2024 show?

Full on preppy looks, with the polo shirt being the star of the show.

When it comes to impact on fashion trends, Miu Miu tends to be the show that everyone looks to in order to guide us. And it has always been one of my favourites since the 90s.

In the ever-evolving world of fashion, certain styles have withstood the test of time, and have maintained their timeless allure, leaving an indelible mark on the sartorial landscape.

Among these enduring aesthetics, preppy style stands out as a beacon of classic sophistication and collegiate charm.

Originating from the elite preparatory schools of the Northeastern United States, preppy fashion transcends its academic roots to become a symbol of refined elegance and understated grace.

With its signature blend of clean lines, vibrant colours, and a nod to tradition, the preppy aesthetic has evolved into a versatile and enduring wardrobe choice that effortlessly merges a sense of ease with an unmistakable air of polish.

A 12 Piece Preppy Capsule Wardrobe for Winter

A white background with 12 pieces and accessories for A 12 Piece Preppy Winter Capsule Wardrobe.

Cream Sweater | Jeans | Riding Boots | Headbands | Brown Handbag | Blazer | Brown & Red Handbag | Turtleneck | Cape Fringe Scarf | Black & Red Tote | Green Cords | Striped Polo Shirt | Navy Polo | Penny Loafers | Red Sweater | Gloves | Beret | Red Heels | Brown Sweater | Sneakers | Sunglasses | Tan Trousers | Blue Button Up | Red Socks | Heeled Boots | Belt | Navy Trousers

What is the History of Preppy Fashion?

Preppy fashion, short for “preppie” or “preparatory,” originated in the United States and has its roots in the Ivy League culture of the 1950s and 1960s, but it actually began before that.

In the late 1890s and early 1900s, preppy fashion served as a distinctive status marker, adorning affluent men attending preparatory and Ivy League institutions — thus earning its name.

Essential wardrobe pieces for this elite group included Brooks Brothers button-down shirts, knit sweaters, and loafers, and as the 1930s unfolded, college women embraced this style trend as well.

The introduction of the first “Lady Levi’s” in 1934 marked a pivotal moment, propelling jeans into the realm of major preppy fashion, a shift that has endured through the years.

Thank you for the lady Levi’s, although I often wear men’s.

So the term “preppy” is derived from “preparatory schools,” which are private secondary schools known for their traditional and often elite education.

The style became popularized through fashion and cultural influences, reflecting a certain East Coast, upper-class aesthetic.

The preppy aesthetic emerged among the students of Ivy League universities such as Harvard, Yale, and Princeton during the 50s and 60s.

The clothing was characterized by clean lines, classic cuts, and a focus on durability and functionality.

Key pieces included polo shirts, button-down shirts, khaki pants, blazers, loafers, and accessories like pearls and ties.

The iconic American clothing retailer, Brooks Brothers, played a significant role in popularizing preppy fashion. The brand was known for introducing key preppy items like the button-down collar shirt and the polo shirt.

The preppy style surged into mainstream popularity during the 1970s and 1980s, in part propelled by its prominent portrayal in popular culture.

Icons such as Princess Diana and Brooke Shields became synonymous with the preppy aesthetic, showcasing their fondness for turtlenecks, tartan blazers, and an elegant infusion of sport-chic elements.

Movies like “Love Story” and “The Great Gatsby,” as well as the television series “Ivy League Look,” contributed to the widespread adoption of preppy fashion.

Designer Ralph Lauren played a crucial role in shaping and promoting the preppy style.

His Polo Ralph Lauren brand, established in 1967, embraced the aesthetic of the East Coast elite, but with affordability, featuring items like the polo shirt, cable-knit sweaters, and khaki pants.

Preppy became a subculture with its own set of codes and symbols.

The style was associated with a certain lifestyle, often perceived as affluent, conservative, and academically focused.

In the 1990s, the popularity of preppy fashion waned as other styles gained prominence.

However, there have been periodic revivals at various points, with designers revisiting and updating classic preppy pieces.

But the core of preppy fashion continues to influence contemporary styles.

Today, preppy style remains a classic and enduring fashion choice for many individuals, and it continues to be a part of the broader landscape of fashion.

It’s not just about clothing but also encompasses a certain attitude and lifestyle associated with tradition, education, and a refined aesthetic.

What are some preppy wardrobe staples for winter?

Preppy style for women is characterized by classic, timeless pieces that exude an air of sophistication.

A well-fitted white button-down shirt is a versatile and essential piece. It can be dressed up or down for various occasions.

A classic cable-knit sweater in a neutral colour is perfect for both casual and more polished looks.

Try a polo shirt in pastel shades, classic white, or striped because it is a quintessential preppy item. It can be worn through every season and looks great layered both over and under.

A tailored blazer adds a polished touch to any outfit. Navy or camel are popular preppy colours for blazers.

Bonus points if you can find a collegiate one secondhand.

Look on Etsy.

We want a variety of trousers in wide leg, ankle length, and corduroy for this season, in a variety of colours as well.

Include classic shoes like riding boots, penny loafers, ballet flats, and retro style sneakers to give a modernized preppy look.

A timeless trench coat is a practical and stylish outerwear option that complements the preppy aesthetic in certain climates. For colder temperatures pick a wool coat in a camel, black, navy, or even a tartan print.

I didn’t include a winter coat in this one because I want to focus the 12 pieces on the actual wardrobe, not on outerwear which we tend to alternate between a few pieces throughout the season.

One, nice, and long wool coat in a slightly oversized fit so that you can layer underneath is a good choice.

For this wardrobe, I would choose camel, or chocolate colour, or maybe a plaid in similar tones. For something bold I would choose red.

A mid-length pleated skirt in a neutral colour or plaid/tartan skirt adds a touch of preppy flair to your wardrobe. Winter fabrics like wool, leather, and suede are great options and add a lot of texture to a look.

Pair it with tights for colder weather.

Always have a variety of sweaters in various colours and fits. Make sure that at a minimum you can layered a turtleneck underneath them.

Preppy looks are modernized and built by layering.

Incorporate a structured tote bag for a functional accessory that complements preppy style.

And don’t forget the use of scarves in winter. Try classic prints like stripes, polka dots, or plaids to add a pop of colour to your preppy winter outfits.

But also seek out styles that are interesting and long so you can drape them in artistic ways and easily dress up your look.

In 2023 going towards 2024, preppy style for women continues to blend classic, timeless pieces with modern twists.

The core elements of preppy fashion often include well-tailored clothing, clean lines, and a sophisticated colour palette.

Modern preppy styles for women may also incorporate contemporary trends, such as sustainable and ethical fashion choices, updated silhouettes, and a mix of high and low fashion pieces.

Overall, the essence of preppy style remains rooted in a combination of elegance, comfort, and a nod to tradition.

And if there is one piece that you should grab now in preparation for spring and summer, I recommend the polo shirt because it’s going to be huge.

*I want to note that Black Friday sales started and the stock of many of these things may go quickly, but as of the time of the post, everything was still in stock.

Preppy Outfit Ideas for Women

A white background with 12 outfits for A 12 Piece Preppy Capsule Wardrobe.

A white background with 12 outfits for A 12 Piece Preppy Capsule Wardrobe.

Cream Sweater | Jeans | Riding Boots | Headbands | Brown Handbag | Blazer | Brown & Red Handbag | Turtleneck | Cape Fringe Scarf | Black & Red Tote | Green Cords | Striped Polo Shirt | Navy Polo | Penny Loafers | Red Sweater | Gloves | Beret | Red Heels | Brown Sweater | Sneakers | Sunglasses | Tan Trousers | Blue Button Up | Red Socks | Heeled Boots | Belt | Navy Trousers

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Sara

Sara is the founder and creative behind livelovesara. A George Brown College Fashion Styling Graduate, she provides advice on finding your personal style regardless of age and budget. She is always on the hunt for the perfect wardrobe piece and is a vintage and thrifting enthusiast who can't wait to share her newest finds. She is also trying to learn French.

One Comment

  1. Hi, Sara,
    I LOVE your wardrobes. This preppy one is fantastic. I live in Virginia, USA, so the preppy style is always in style here. It’s so fun to mix it with more modern & vintage pieces! I’ve been following you for years. I’m a commercial interior designer, so I love all things fashion & art. I used to live in Italy & always love your travel wardrobes. Keep up the excellent work.

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