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?

So, first, what exactly 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.

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.

As a preppy style personality, 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 to see which style you are most drawn to.

You appreciate clean-cut styles

We 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.

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

If you do love a preppy style aesthetic, you’re in luck as preppy style and check prints are very much on trend at the moment. Carmen @carmen_gimeno above slings a sweater over her shoulders to add even more preppy style to her check suit.

Steal her look with this similar blazer, pants, sweater, sneakers, handbag, belt and sunglasses.

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 33 essentials every woman over 40 should have in her closet.

You have a lot 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.

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

Kim @kimair above (read her style interview here) layers her shirt under her dress.

Recreate her outfit with this similar polo dress, shirt, sneakers, clutch, earrings and sunglasses.

You love a dress or shirt with a collar

While you’ll wear t-shirts and boat necks too, collared clothing styles such as the peter pan collar, classic button-down shirt or shirt dress and the polo style are among your favorite looks.

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 in a skirt and you probably have equal numbers of each in your closet.

Preppy style women

celebrities with a preppy style | 40plusstyle.com

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

But preppy style clothing is also loved by Alexa Chung (above, right, 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. She loves blazers and pussy bow necklines.

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

Designer labels' preppy fashion | 40plusstyle.com

Ralph LaurenPaul SmithStella McCartney

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. Gucci and Prada have also increasingly been fans of the preppy style in recent seasons, and Paul Smith and Stella McCartney are also definitely worth looking at for inspiration.

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

Preppy clothes and accessories

Now, let’s take a look at some of the best clothing, shoe and accessory styles to get a preppy look. Plus, read on and you’ll find a capsule wardrobe especially put together for the preppy style personality this summer.

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

Polo RL Classic Fit Mesh Pony ShirtMarie Marot X J.Crew Poplin ShirtMing Wang Crepe Tie Neck Sleeveless BlouseLoveappella Stripe Button Shoulder T-Shirt

Knitted vest and pants outfit | 40plusstyle.com

Aoysky Sweater VestMarie Marot X J.Crew Poplin ShirtJ.Crew Kate Cotton Blend Straight Leg PantsTommy Hilfiger Balie Slip-On Platform SneakerLongchamp Large Le Pliage ToteMadewell Front Facing Freshwater Pearl Circle Hoop Earrings

Preppy sweaters

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. You could also look for a sleeveless sweater to wear over your shirt.

Cardigans and jackets to wear for women with a preppy personality | 40plusstyle.com

J.Crew Relaxed Cotton Linen Blend Beach SweaterJ.Crew University Terry V-Neck Stripe Polo ShirtJ.Crew Contras Trim Cable Knit Cardigan SweaterAoysky Sweater Vest

Marie-Louise wears a v-neck sweater and full skirt| 40plusstyle.com

Marie-Louise @mrsmlmode above opts for a classic preppy look of a v-neck sweater worn over a stripe shirt.

Recreate her outfit with this similar sweater, shirt, skirt and sneakers.

Preppy style outerwear

For transitional months or cooler evenings, you can invest in a padded, yet fitted, vest which you can wear over your shirts and v-neck sweaters.

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.For winter choose a warm duffle coat with a toggle fastening.

Preppy outerwear | 40plusstyle.com

Halogen Oversize Double Breasted Linen Blend BlazerTreasure & Bond Oversize Plaid Blazer Karen Millen Oversized Tab Detail Belted Longline TrenchWantdo Winter Thicken Jacket

Trench coat and jeans outfit| 40plusstyle.com

Karen Millen Oversized Tab Detail Belted Longline TrenchPolo RL Classic Fit Mesh Pony ShirtJ.Crew Slim Wide Leg JeansTommy Hilfiger Hazen Loafer PumpHOBO Sheila Leather Crossbody BagTory Burch Kira Enamel Circle Stud EarringsCoach Tatum Bracelet Watch

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. A sailor style will also appeal to you.

Jeans and pants | 40plusstyle.com

J.Crew Slim Wide Leg JeansJ.Crew Kate Cotton Blend Straight Leg PantsJ.Crew Lightweight Chino Straight Leg Essential PantsJ.Crew Collection Ingrid Italian Seersucker Pants

Patricia wears an all beige outfit | 40plusstyle.com

Patricia @patriciaafricaiglesias above (read her style interview here)  mixes elements of preppy and classic style in her all-neutral outfit, and then adds glamour with her jewelry and accessories.

Check out this similar sweater, shirt, trousers, pumps, bag, earrings, belt and sunglasses.

Preppy dresses and skirts

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

Look out for styles featuring pleats which will go perfectly with your 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. Choose dresses with collars, full skirts, stripes and pleats.

Dresses and skirts | 40plusstyle.com

J.Crew Maxi Luster Crepe Slip DressJ.Crew Marie Marot X J.Crew Cotton Poplin Tie Waist ShirtdressJ.Crew Square Neck A-Line Midi DressJ.Crew Pleated Pull-On Midi Skirt

Collared dress and flat shoes outfit | 40plusstyle.com

J.Crew Maxi Luster Crepe Slip DressFranco Sarto Tiari Chain Square Toe LoaferKate Spade New York Kisslock Woven ClutchTory Burch Kira Enamel Circle Stud EarringsTasha Woven Headband

Preppy shoes

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

You aren’t too keen on heels and you definitely don’t like to be uncomfortable. Instead, look out for loafers with bows or tassels, a pair of brogues or Oxfords and flat knee-high boots for the cooler months. For summer, you could look for sneakers or boat shoes. For more formal occasions, you might like Mary Janes, either flats or with a heel.

Preppy shoes | 40plusstyle.com

J.Crew Winona Spazzolato Leather Lug Sole Penny LoafersFranco Sarto Tiari Chain Square Toe LoaferTommy Hilfiger Hazen Loafer PumpTommy Hilfiger Balie Slip-On Platform Sneaker

Shan wears a black suit and loafers | 40plusstyle.com

Shan @teachingonthegc above chooses a classic pointed loafer style with her suit.

Steal her look with this similar shirt, blazer, pants, loafers and scarf.

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. Headbands are particularly on-trend right now and are a key component of preppy style.

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

Longchamp Large Le Pliage ToteHOBO Sheila Leather Crossbody BagKate Spade New York Kisslock Woven ClutchKate Spade New York Bouquet Toss Pendant NecklaceTory Burch Kira Enamel Circle Stud EarringsMadewell Front Facing Freshwater Pearl Circle Hoop EarringsCoach Tatum Bracelet WatchTasha Woven HeadbandTreasure & Bond Stripe ScarfLauren Ralph Lauren Stripe Scarf

Striped sweater and chinos outfit | 40plusstyle.com

J.Crew University Terry V-Neck Stripe Polo ShirtJ.Crew Lightweight Chino Straight Leg Essential PantsJ.Crew Winona Spazzolato Leather Lug Sole Penny LoafersLongchamp Large Le Pliage ToteMadewell Front Facing Freshwater Pearl Circle Hoop EarringsCoach Tatum Bracelet Watch

Brands if you love a preppy style

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

There are plenty of preppy clothes brands, both designer and from the high street which cater to the preppy aesthetic. These are some of our favorites. How about you? Which are your go-to preppy clothes brands?

Below are 9 preppy outfits created from the wardrobe choices above

Below you will find many of the clothing and accessory options put together in a capsule wardrobe for summer. You could easily mix and match many of the tops and bottoms to create many different outfit options.

Also, read our ultimate guide to creating a capsule wardrobe that works best for you.

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

shop the preppy pieces above here:

Take a look below at our previous season preppy capsules. You can see this is such a timeless style that all of the items featured would still look just as good this season and beyond.

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

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 Carmen @carmen_gimeno


Sylvia is 40+style’s editor-in-chief and has been helping women find their unique style since 2011. She is devoted to empowering women of any age to look and feel their best. Read more about Sylvia and 40+style on this page.

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