This post sheds light on the roots of Ivy League aka preppy style. It explains what does Ivy League Style mean and identifies the key elements to get the look. Furthermore, the post addresses how to style its ultra-feminine pieces in a way that you are taken serious at any age. Read how to wear feminine preppy outfits, get inspired by the preppy style outfit ideas, and make it your signature style.
- What is the Origin of the Term Preppy?
- What is Preppy Style?
- Preppy Style’s evolution from Sub-culture to Mainstream Fashion
- How to Have Preppy Style?
- Best Cut for Ageless Style in Feminine Prints
- Can You Wear a Preppy Look at Work over 40
- Preppy Gingham Shirt Outfit Inspiration
- Wrapping Up How You Can Wear Feminine Preppy Outfits
Disclosure: There are affiliate links in this post.
What is the Origin of the Term Preppy?
The term preppy originally goes back to the private North Eastern United States college preparatory schools for the upper class kids in the 20th century. It refers to the alumni of these schools. These schools trained their students in speech, etiquette, manners and dressing to identify themselves as upper class off-springs. The goal of sending the kids to these schools was to prepare them for best chances of admission to one of the Ivy League oldest universities of the region like Harvard, Princeton and Yale. These schools and colleges served also to be socio-economically well connected. By the mid-century, Brooks Brothers and J. Press had stores on these old campi.
In the 1960s, it became more common to also spend tuition on having the daughters attend these prep schools and colleges. Consequently, the most feminine pieces of preppy have the roots in the fashion of this time.
Together these types of clothing are the roots of Ivy League dressing.
What is Preppy Style?
Now what does Ivy League Style mean? Obviously, the style has its roots in these prep schools and the traditional college tradition of Ivy League going back to the early 20th century. Preppy as a sub-culture youth style emerged in the late 1970s with college and upper class recreational clothing. Think all kind of clothing needed for activities like polo, tennis, riding, hunting, sailing and golf plus college blazers, college shoes, boat and tennis shoes. It brands were Brooks Brothers, Orvis, L.L. Bean in the Northeast. Due to the different requirements for dressing for the weather in the Pacific Northwest, Eddie Bauer was the Must-have on the Westcoast. Lilly Pulitzer was a favorite among the young women.
Preppy Style’s Evolution from Sub-culture to Mainstream Fashion
In the 1980s, many key elements of preppy became mainstream fashion, for instance, white tennis socks with college shoes, sailors-shirt, polo shirt, college blazer. Lacoste, Dooney and Bourke joined the bandwagon.
How to Have Preppy Style?
Here a list of the key elements of Preppy: Wrap dresses, 1960s and 1970s inspired ensembles and tailored skirt suits, shift dresses, nautical and equestrian inspired clothing, boat shoes, riding boots, college shoes, college and riding blazer, cashmere/wool knit-tops, silk shirts and blouses, refined jewelry, briefcase. Think Kate Middleton prior to becoming a member of the Royal family.
Best colors for dresses, blouses and shirts are pastels.
Key pattern are nautical stripes and gingham.
Best Cut for Ageless Style in Feminine Prints
Gingham belongs to pattern that are considered ultra-feminine. Other über-feminine prints and fabrics are polka dots, pin dots, floral prints and lace. However, these prints do not belong to Ivy League Style.
Remark: When you have many pieces in gingham, polka dots, pin dots, floral prints and lace, you personal style is most likely Romantic Style.
Unfortunately, these very feminine pieces have in common that they lean into the cute, naïve territory when paired with certain cuts. However, in a classic cut, a gingham shirt looks very preppy.
The goal of Preppy Style is to look well-educated, sophisticated and knowledgeable, elite.
Can You Wear a Preppy Look at Work over 40
Sure, you can wear Ivy League Style at work. It all nails down to how to wear ultra feminine prints at the office.
Tip: The trick to look serious in ultra-feminine pieces is to style them with classic or casual pieces.
Preppy Gingham Shirt Outfit Inspirations
The photos below show a preppy feminine outfit inspiration with gingham that works for us over 40.
Wrapping Up How to Wear Feminine Preppy Outfits
Stay on the classic side with cuts. Go for your flattering colors. Stay away from everything that looks naïve. When you can’t afford the Ivy League brands, go for the highest quality you can afford.
Interested in more dressing tips? Then my style book “how to Dress for Success in Midlife” is perfect for you. Buy the book now.
Photos: G. Kramm
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Well aren’t you just CUTE AS A BUG in your preppy style?? And you’ve definitely got me wanting to do a HIGH KICK in my next photoshoot!!! SPECTACULAR!!!!
Great looks. Thank you for the style inspirations.
Rena
I was a big wearer of the preppy style and still like the crisp look of that style. That’s a good tip to add a feminine piece with this look, Nicole! You look great in every style!
xx Darlene
I’m all about preppy looks and gingham always makes it feel springy!!
XOOX
Jodie
Such a fun casual look today, Nicole!
Rosemary
This is a pretty look, and I love the stockings with the gold sandals. Your beret is sweet on you!
Fabulous looks. Love the skirt in the first picture.
Nicole, that first outfit is so amazing! I just pinned it to my Outfits to Copy board. I really want to recreate this fabulous look except I don’t have a skirt like yours. I am going to be on the lookout for something similar in style and print. I do love a little splash of preppy style now and then! Fun post!
Shelbee
A great casual look, great boots too. Jacqui Mummabstylish
This is a fun look, Nicole. I’ve been meaning to pull my gingham top out, but it still feels a bit too spring-y.
You can never go wrong with gingham! I just love those red boots with this top!
Carrie
Very cute spring look, Nicole! I really like how you elevated your gingham shirt by popping the collar and adding red pumps to your look. You are giving me some good ideas!
I absolutely love red gingham for spring! This is such a great outfit!
Shelbee
Nice outfit. I love gingham.
I love the gingham, so perfect with jeans. Thank you for the shout out Nicole!
Debbie
I love gingham but funny enough, I havn’t got anything gingham in my closet at this moment. I see a shopping day coming!!