These Wardrobe Staples Are Must-Haves to Master the Preppy Look

If there’s one sense of style that’s truly aspirational, it has to be the preppy look. With only the finest fabrics, conservative cuts, and timeless accessories, it’s no wonder this look is so difficult to pull off. Fortunately, we know exactly which staple pieces you need to turn yourself into a full-blown prepster. With fewer than 15 essential items, you can have the complete preppy wardrobe of your dreams. Read on to see which pieces to start shopping for (and monogramming) today.

1. A luxurious leather tote bag

Fashionable beautiful big red handbag on the arm of the girl

Get a gorgeous tote to up your style game. | iStock.com/alexalenin

Being preppy is more than just a look — it’s a lifestyle. Preppy women ostensibly have a lot going on. Their schedules are packed with things to do, places to be, and people to see. As such, it’s only fitting that a preppy woman carries a large bag. Whether you prefer a Kate Spade Cameron Street Tote or a Tory Burch Gemini Link Tote, you can be sure that this bag style will accommodate the needs of your busy life (bonus points if you also have a matching wallet).

2. Stacks of cashmere

Stack of cozy knitted warm sweater

When you buy sweaters, cashmere should be the go-to material. | iStock.com/Stas_V

If there’s one material that prepsters love, cashmere wins hands-down. And by love, we mean no item of clothing is excluded from consideration. True preppy dressers want to have everything from cashmere pullovers to cardigans, pajamas, and socks. So when in doubt, ditch cotton and invest in cashmere.

3. A pearl jewelry set

Elegant woman wearing pearl jewelry

Pearls are actually a girl’s best friend. | iStock.com/KatarzynaBialasiewicz

In most cases, diamonds are a girl’s best friend. However, for the preppy woman, the finest jewelry is made of pearls. There’s nothing quite as timeless and elegant as a set of pearl earrings, a bracelet, and a necklace. They’ll match with absolutely everything in your wardrobe, and can hold precious sentimental value if they’ve been inherited as heirlooms.

4. A beige trench coat

Female hand on a tie belt

A classic trench will ensure you always look good. | iStock.com/ iprogressman

No matter where you are in the world, you can’t let poor weather ruin your look. To stay on trend in any forecast, make sure you have a beige trench coat in your closet. This classic staple is easy to throw on as you run out the door, and it’s incredibly versatile, so you can play it up or keep it casual. Our first choice will always be the original Burberry Sandringham Long Heritage Coat, but there are also plenty of affordable options, such as the London Fog’s Double Breasted Trench Coat.

5. Riding boots

Woman wearing brown boot

Riding boots are functional and look great. | iStock.com/olcayduzgun

Is anything preppier than being an equestrian? The short answer: no. So, it makes perfect sense that preppy fashionistas adore leather riding boots. A pair of chestnut, knee-high leather riding boots are particularly great during autumn, as they’ll add an element of class you won’t find in snow boots or chelsea boots.

6. Colorful but conservative dresses

a series of bright modern fashion women's dresses on hangers

Bright, whimsical dresses are a prepster fashion staple. | iStock.com/iprachenko

If you peak into a preppy woman’s closet, you’ll most definitely find an array of whimsical dresses. It’s important to note the pops of color do all the attention grabbing, not the dresses’ cut. You won’t find super-short cocktail looks, bodycon dresses, cut-outs, or anything of the sort in a preppy wardrobe. Instead, women keep their dresses conservative, and always along the lines of something you’d wear to have lunch with your in-laws.

7. A classic watch

Female watch on the wrist

A beautiful watch can really up your style game.| iStock.com/iprogressman

If there’s one thing preppy women know the value of, it’s a statement accessory you can rely on to make a daily impression. In the same way pearl earrings match with everything, so too does a subtle yet iconic watch. The Cartier Tank, in particular, is a prepster favorite for its ability to complete any outfit. It’ll last you a lifetime, can be passed down to your children, and will never go out of style.

8. Colorful ballet flats  

Green color flat shoes

Go for bold hues when buying flats. | iStock.com/bernashafo

Footwear is a defining characteristic of preppy fashion, so you really need to get your shoe choices right to pull off this look. Although boat shoes, leather loafers, and bespoke slippers are popular, no option is quite as beloved as the colorful ballet flats. Choose your favorite shade and prepare to be comfortable and cute. If you’re new to the world of flats, these Sam Edelman Felicia Ballet Flats are a great place to start.

9. A striped sweater

Woman in a denim shirt, striped t-shirt

A striped sweater looks great and goes with everything. | iStock.com/iprogressman

Basically, you can’t embody the style without stripes. This effortless staple transcends seasons. You can wear your striped sweater with white shorts in the summer, toothpick jeans during spring, and black leggings in winter. Believe us when we say this will be your go-to favorite.

10. Something Tiffany blue  

beautiful blonde woman in turquoise dress

Say hello to your go-to color. | iStock.com/SergeBlack

If there’s one color the preppy crowd can’t get enough of, it’s Tiffany blue. So if you plan on mastering the preppy look, you’ve got to add an item in this specific shade of teal to your closet. We advise you to consider a sheath dress, silk scarf, or hand bag in the hue.

11. Fringe scarves

Pretty woman with coffee in hand walks

You need a scarf anyway, so go for this type. | iStock.com/Ales_Utovko

During the colder months, the preppy look calls for a fringe scarf (preferably made of cashmere, as we mentioned before). Many preppy women like the look of a plaid fringe scarf with white clothing, or a cream colored fringe scarf with black clothing. Simply tie this staple around your neck, tuck it into your puffer vest, or layer it beneath a wool peacoat.

12. Knee-high rain boots

Autumn. The harvest of apples. Rubber boots Burgundy

Pick a fun color to show off your fashion sense. | iStock.com/Oleh_photographer

Generally speaking, functional, element-proof attire is perfect for a prepster’s wardrobe. A prime example of their functional sartorial choices are knee-high rain boots, which keep them dry and looking stylish. Invest in a pair of Hunter Rain Boots to maintain your sense of fashion when the weather looks overcast.  

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