If your favorite style icon is Ali MacGraw in Love Story, then you almost certainly have a preppy style personality.

An all-American style which is inspired by prep school attire, this is a way of dressing which can transcend seasons, and generations.

What is preppy style?

This collegiate-inspired style is casual in the main, but that doesn’t mean that your closet will be totally full of denim and jeans.

You also love to wear skirts and dresses as well as classic blouses with pussy bows or Peter Pan collars.

Sally (below) adds a touch of pink to her preppy outfit.

Check out this similar pink sweater, striped blouse and midi skirt.

how to get a preppy style | 40plusstyle.com

How to tell if you have a preppy style personality

A preppy style has a lot in common with classic style so you may well find that you are drawn to elements of both. It can also draw inspiration from natural style.

You love cozy knits, checks and stripes and prefer to wear flat shoes and natural fibers, including leather as well as wool.

If you aren’t sure what your style is, you could take this fun style personality quiz.

You appreciate clean-cut styles

I won’t find you in distressed jeans or a moto jacket. Instead you prefer a blazer, a v-neck sweater and a classic jeans style like bootcut or straight-leg.

You aren’t trend obsessed

It’s much more important to you to have a good closet of essentials than to shop for a statement piece each season.

For more inspiration take a look at the 28 essentials every woman over 40 should have in her closet.

You have a love of stripes

If there’s one pattern you have in your closet, it will be stripes. That’s because as well as being college-inspired, the preppy look also has a nod to the nautical.

You don’t have a preference for pants or skirts

While preppy style is generally comfortable, you are just as at home in a pair of pants as you are a skirt and you probably have equal numbers of each in your closet.

Preppy style women

The preppy style is one that has been adopted by many younger celebrities in recent years, including Emma Watson and Olivia Palermo.

celebrities with a preppy style | 40plusstyle.com

But it’s also loved by Alexa Chung (who combines preppy with some bohemian), who is in her fourth decade, and Gwyneth Paltrow, who combines preppy with classic style. Reese Witherspoon is also often seen sporting a preppy look.

celebrities with a preppy look | 40plusstyle.com

Kate Middleton also often dresses in a preppy style both off-duty and on.

Plus, there are plenty of women from years gone by who could show them all a thing or two. Fashion designer Lilly Pulizter epitomized preppy style, whereas no-one wore a twinset better than Jackie O or Grace Kelly.

Designers you like if you love preppy fashion

As the preppy style is really an all-American look, your preference tends to be for American designers including Ralph Lauren, Tommy Hilfiger and Thom Browne.

All of these appeal to your love of a clean-cut, classic style with a little hint of “geek” chic.

Designer labels' preppy fashion | 40plusstyle.com

Tommy HilfigerThom Browne – Ralph Lauren

Tops to get the perfect preppy look

The preppy style personality really goes for two main options when it comes to tops.

You will want to make sure you have plenty of casual options in your closet, including a classic polo neck and Breton-striped top.

But, you also like ladylike, dressy blouses and will often choose to dress up your jeans with pretty blouses featuring Peter Pan collars or pussy bow detailing.

preppy tops to wear | 40plusstyle.com

Madewell vintage teePolo Ralph Lauren polo shirtRomwe collared topAnn Klein tie neck blouse

how to get a preppy style | 40plusstyle.com

Elena (above) shows how to add a little preppy style with her neck scarf.

Here is a similar button down shirt to pair with a long denim pencil skirt.

preppy style sweaters and vests

A classic sweater and a cardigan is definitely vital to achieving a preppy style.

For a true preppy look, choose a v-neck and look out for details such as cable knit as well as varsity or cricket-style stripes.

For fall, invest in a padded, yet fitted, vest which you can wear over your shirts and v-neck sweaters.

sweaters and vests to wear for women with a preppy personality | 40plusstyle.com

Tommy Hilfiger knit sweaterHilfiger Collection knit cardiganTommy Hilfiger v-neck sweaterBarbour gilet

combining classic and preppy style | 40plusstyle.com

‘Follow Me and My Style’ (above) shows off a style which is mainly classic but which has a preppy vibe.

Get this similar long vest, long sleeved blouse and jeans to recreate her look.

preppy style coats and jackets

I really struggled to choose between a belted wool coat here and a very similar style in a trench coat.

In the end, the wool coat won because it is so very similar in style to the one Ali MacGraw wore as Jennifer Cavalleri in Love Story.

You will also want to add a classic blazer as well as a quilted coat. Plus, you could think about adding a classic pattern such as plaid.

jackets and coats for a preppy style | 40plusstyle.com

Ralph Lauren wool wrap coatKenneth Cole plaid coatCourt & Rowe tweed blazerBarbour quilted utility jacket

wearing a shirt and sweater for a preppy style | 40plusstyle.com

Nagore (above) wears her shirt under her sweater in a style which combines preppy and classic.

Check out this similar wool coat, sweater and skinny jeans.

Jeans and pants for the preppy style personality

When choosing jeans and pants, you won’t be looking for the very latest hem style or for jeans with holes in them.

Like the rest of your look, you like a clean cut look which could transcend decades.

You will want a classic jeans style as well as looking out for options with patterns such as checks and for pants which have a defined crease.

jeans and pants | 40plusstyle.com

J Brand straight leg jeansHue denim leggingsTopshop wide trousersMarks & Spencer check trousers

a matching suit for the preppy style personality | 40plusstyle.com

Grace (above) looks beautiful in her preppy-style suit.

Get a similar pair of crop suit pants and pair it with this red blazer to copy her look.

preppy dresses and skirts

You will probably have an equal number of pants to skirts if I were to take a look in your closet.

Look out for styles featuring pleats and Peter Pan collars. As a preppy style, you could opt for a shorter skirt length if you are confident about your legs.

You can always wear a shorter skirt with opaque tights. Or you could choose a knee-length or midi option.

Just as with the belted coat above, I couldn’t resist this red dress as it looks just like the one Ali Macraw wore when she met Oliver’s father, Oliver Barrett III.

dresses and skirts | 40plusstyle.com

Ted Baker London skater dressVetior swing dressAnne Klein pleated skirtBoden tweed skirt

Nadya wearing a striped top, midi satin skirt and slides | 40plusstyle.com

Nadya (above) pairs stripes with her midi skirt. She gives her look an extra preppy vibe by wearing her sandals with striped socks.

Here is a similar satin midi skirt you can pair with a stripe sweater.

Preppy shoes

Like the rest of your look, your shoes will be very classic styles. They will also, usually, be mainly flat.

You aren’t too keen on heels. Instead, look out for loafers with bows or tassels, a pair of brogues or Oxfords and flat knee-high boots for winter and fall.

preppy shoes | 40plusstyle.com

Cole Haan tassel loaferVery Volatile knee high bootMichael Kors ballet flatHispanitas oxford

a preppy striped outfit | 40plusstyle.com

Kylie (above) takes elements of the preppy style for her striped look above.

Here is a similar pair of suede boots.

Accessories to go with your preppy clothes

When it comes to accessories, you like to be understated rather than flamboyant.

You love a classic satchel, some well-made leather gloves which will last you for years and, of course, a long wool scarf.

Your jewelry will be tasteful and understated, like the rest of your wardrobe, so you might only choose to add a pair of diamond or pearl stud earrings and a watch for your day-to-day outfits.

accessories to use with your preppy clothes | 40plusstyle.com

Sole Society satchelDaniel Wellington watchQuay Australia optical glassesVolcom pompom beanieMax Mara leather glovesKate Spade stud earringsAllSaints wool scarf

Patricia in a blue sweater with white inner, midi skirt, boots and beret | 40plusstyle.com

Patricia (above) gives her preppy style some added flair by adding a beret.

Steal her whole style with this similar sweater, collared blouse, midi skirt, boots, beret, sunglasses, hoop earrings and bag.

Here are 9 preppy outfits created from the wardrobe choices above

Read our ultimate guide to creating a capsule wardrobe that works best for you.

A capsule wardrobe for the PREPPY style personality | 40plusstyle.com

Preppy brands

If you love a preppy style, then you’re definitely in luck.

There are plenty of brands, both designer and from the high street which cater to the preppy aesthetic. These are some of my favorites. How about you?

Continue reading:

  1. Want To Discover Your Style Personality? Take This Fun Quiz!
  2. Understanding The Different Styles
  3. A Capsule Wardrobe For The Classic Style Personality

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A style guide and capsule wardrobe for the PREPPY style personality | 40plusstyle.com

Feature image by Patricia

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