You are currently viewing Your Guide to Wear Feminine Preppy Outfits
Smithsonian Tee, Pendelton pleated plaid skirt, Hipstik pantyhose, Ruby belt, Hermes collier de chien bangle, (all own) and beret c/o Tenth Street Hats

This post sheds light on the roots of Ivy League aka preppy style, identifies the key elements to get the look, and 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 and make it your signature style.

  1. What is the Origin of the Term Preppy?
  2. What is Preppy Style?
  3. Preppy Style’s evolution from Sub-culture to Mainstream Fashion
  4. How to Have Preppy Style?
  5. Best Cut for Ageless Style in Feminine Prints
  6. Preppy Gingham Shirt Outfit Inspiration
  7. Wrapping Up How You Can Wear Feminine Preppy Outfits
  8. Top of the World Style linkup party No. 300

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 NorthEastern United States college preparatory schools for the upper class kids in the 20th century. It is used for describing the alumni of these schools. Their students were trained 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 Havard, 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 daugthers 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?

Oviously, 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.

stylist in plaid pleat skirt, graphic Tee, belt sandals

blogger wearing a feminine preppy outfit of pleated skirt, T-shirt, beret
Smithsonian Tee, Pendleton pleated plaid skirt, Hipstik pantyhose, Ruby belt, Hermes collier de chien bangle, Fine Dance Shoes sandals (all own) and beret c/o Tenth Street Hats

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 band wagon.

American classic weekend look with C&C subscription box jewelry

Bling Buzz classic American weekend outfit with Cate & Chloe jewelry
Outfit details: The Limited polo shirt, Loft skirt, eric michael suede wedges, Ray Ban sunglasses (all own) with green germ pendant necklace, earrings and cuff ring c/o Cate & Chloe

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 equestarian 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. See this guide how not to look old in pastels.

Key pattern are nautical stripes and gingham.


style book author wear feminine preppy outfit in straight tweed skirt, cashmere sweater


over 50 years old blogger showing how to wear feminine preppy outfits in gray skirt citrus sweater, tall boots
Eddie Bauer straight tweed skirt, Italic cashmere sweater, Rebecca Collins necklace, Vince Camuto boots, Hermes collier de chien bangle, Nordgreen watch, Hipstik tights


Best Cut for Ageless Style in Feminine Prints

Gingham belongs to pattern that are considered ultra-feminine. Other über-feminine prints and fabrics (but not belonging to Ivy League Style) are polka dots, pin dots, floral prints and lace. Unfortunately, these very feminine pieces have in common that they lean into the cute, naïve territory when paired with certain cuts. However, when gingham pieces are cut right, they can look very preppy. You can find the gingham shirt review post with two other preppy looks at the link.


Stylist’s remark: When you have many pieces in gingham, polka dots, pin dots, floral prints and lace, you personal style is most likely Romantic Style.


The trick to look serious in ultra-feminine pieces is to style them with classic or casual pieces. #preppystyle #preppyoutfit Click To Tweet


The goal of Preppy Style is to look well-educated, sophisticated and knowledgeable, elite.


Preppy Gingham Shirt Outfit Inspirations

The photos below show a preppy feminine outfit inspiration with gingham that works for us over 40.


Nicole showing off the heel height of her red booties standing on one leg

Nicole of High Latitude Style in preppy Casual Friday work outfit

in feminine blouse with denim pants and high heels

mature blogger in posh denim and gingham spring look

over 50 years old fashion blogger in red, white and blue preppy LOTD
Detail info: Manolo Blahnik booties, Kieselstein Cord belt and buckle, statement garnet necklace, Ray Ban vintage sunglasses Hermes collier de chien bangle, Festina watch (all own), boyfriend jeans c/o Kut of the Kloth and gingham shirt c/o Whistle River


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.

Take a look at this guide on how to wear feminine preppy outfits. #agelessstyle Click To Tweet
so your friends can see it too.

Do you like the different vibe of the gingham shirt in this outfit?

Interested in more dressing tips? Then my style book “how to Dress for Success in Midlife” is perfect for you. Buy the book now.

Top of the World Style linkup No. 300

banner of the weekly Top of the World Style linkup party on Thursdays

Welcome to the Top of the World Style linkup party.

Jennifer wearing feminine preppy gingham pants and a striped top
Jennifer from Curated by Jennifer became the Top of the World OOTD Readers’ Fav. Photo from her post


Claire Justine in jeans with stripe, sneakers, polka dot T-shirt
Claire Justine from Claire Justine oxox became Top of the World Style Winner. Photo from her post


Salazar in preppy skirt sweater riding boots british style
Salazar from 14 Shades of Grey became the Top of the World OOTD My Fav. Photo from her post


Congrats Ladies! Grab your award buttons.


Entrance to the party


See these awesome looks at the Top of the World Style #linkup party. #timelessstyle Click To Tweet


I invite all fashion and style bloggers to co-host the top of the World Style linkup party. Just send me an email with your request. Want to throw your own party?

Photos: G. Kramm

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This Post Has 16 Comments

  1. 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!!!!

  2. Great looks. Thank you for the style inspirations.


  3. aquamarinastyle

    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

  4. Jodie

    I’m all about preppy looks and gingham always makes it feel springy!!

  5. Rosemary Davis

    Such a fun casual look today, Nicole!


  6. Jess

    This is a pretty look, and I love the stockings with the gold sandals. Your beret is sweet on you!

  7. Amy Johnson

    Fabulous looks. Love the skirt in the first picture.

  8. shelbeeontheedge1

    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!


  9. mummabstylish

    A great casual look, great boots too. Jacqui Mummabstylish

  10. fiercefashion

    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.

  11. You can never go wrong with gingham! I just love those red boots with this top!


  12. Jennie

    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!

  13. I absolutely love red gingham for spring! This is such a great outfit!


  14. Julie | This Main Line Life

    Nice outfit. I love gingham.

  15. stinedurfdl

    I love the gingham, so perfect with jeans. Thank you for the shout out Nicole!