The Preppy Woman’s Guide To Denim in a Chino World

Preppy Denim Jeans
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Here in America, and really all over the world, blue jeans have become a major staple in our wardrobes. Any place you go, from casual to dressy, blue jeans are present, which comes as no surprise for their versatility and comfort. From skinny to boot cut, flare, cropped, relaxed, bell bottom, jegging, straight, loose, and much more, blue jeans are constantly evolving in the fashion world. However, for the classy prepster, it’s a tale as old as time, blue jeans are a huge taboo! It truly comes as no surprise, think about it, did you ever see Mrs. Kennedy, Blair Waldorf, Kate Middleton, or Grace Kelly sporting a pair of old Levi’s? We sure have not! When you think of a preppy pair of pants, you most likely think khakis, chinos, madras, or twill, certainly not (gasp) blue jeans! Here at Country Club Prep, we want to keep the classic preppy look up to date and easily attainable for everyone, so we have set out to do the unthinkable. By the end of this article, you and the rest of the preppy community will be well schooled on how to incorporate classic blue jeans into the preppy style without rocking the boat.

We aren’t saying it’s going to be easy, nor will those trendy ripped up jeans be given instant gratification by prepster’s alike, but it is doable, and here’s how. Rule #1, stick to timeless cuts like skinny or straight for women, afterall, boat shoes don’t pair very well with bell bottoms, and boot cut does not necessarily mean duck boots. Rule #2, the wash is very important! Classic white, black, and medium or dark blue are your best options for incorporating denim into a preppy wardrobe, as they will look classic and clean when paired with your favorite sweater, polo, preppy tee shirt, or button down. Rule #3, pay attention to the details, they can make or break the look. Tears, holes, rips, and fray are the biggest offenders here, as they bring down the tailored preppy look. We suggest sticking to denim with no distressing (and so would your mother), although a tasteful frayed hem here and there is quite acceptable. Apart from distressing, steer clear of gaudy stitching or overdone hardware, you want to keep the spotlight on your pearls or KJP watch afterall.

Shopping Guide

#1 The Basic

The key to pulling off denim as preppy is simplicity. These solid navy blue jeans from Southern Tide are the perfect basic to pair with all your bright polos and button downs. No rips or tears and minimal fading on the front ensures you’ll be looking classy and tailored no matter how you style these jeans. We suggest with a striped button down, a bright belt, and Jack Rogers or Sperrys.

#2 The Classic White

They say no white jeans after Labor Day, but how could you resist with such a clean and classic look? White jeans are always welcome in the preppy style, and they pair wonderfully with navy Shep Shirts, bright Gretchen Scott blouses, and punchy Lilly Pulitzer Popovers. We are especially in love with this pair from Vineyard Vines. The simple details don’t steal the spotlight of your outfit, and the slightly frayed hem add a touch of something different to your preppy style. It’s a win-win!


#3 A Hint of Pastel

Every preppy girl loves pastels and the bright summer days they remind us of. Pastel denim is no exception! Nothing says sweet southern style quite like these Ralph Lauren Pink Pony jeans paired with a white blouse, pearls, and Jack Rogers or Tory Burch Millers. All the style of a pastel chino with all the comfort and versatility of denim. Need we say more?


#4 The Light Wash

During the summer months, you might want a classic pair of jeans with a lighter wash than the first pair shown. You can rest assured we’ve found the perfect pair for you. The classic slim cut of these slightly cropped jeans from J. Crew is perfect for a French tuck and will complement a wide variety of body types. Added bonus: the side seams of these jeans have a small line of pink piping that we are in love with!


#5 The Embellished Pair

Every girl needs a pair of party pants! We are in love with these golden polka dot embellished jeans from Lilly Pulitzer, and we know you will be too as soon as you get your hands on them. If you want the most fun and preppy pair of jeans on the market, these are certainly for you. Pair with gold Jack Rogers, pearls, and a white button down (extra points if you pop the collar) for the perfect preppy party look.


#6 For Cozy Days

A Patagonia pullover, camp socks, and Sperry duck boots… sounds to us like the perfect outfit for a chilly fall or winter day! All that’s missing is a simple and comfortable pair of jeans to complete the look. This is where the stretchy jegging comes into play. Soft and comfortable, these Performance Stretch Jeans from L.L. Bean are the perfect basic for your chilly days. PS: the slender ankle opening will tuck into your camp socks so perfectly.


#7 We <3 Stripes

Color block stripes have long been a preppy style staple for their crisp and tailored look. These jeans from Mother bring an exciting flair to classic white denim with a fun cropped cut and bold colors up and down the sides. The perfect nautical look is in your hands when you pair these jeans with Sperry or TorySport sneakers, a bright polo, and (of course) a corded sweater tied around your neck. You’ll be the most preppy and stylish woman on the high seas, or land too…


#8 The Cool Culotte

Old school culottes have finally come back in style, and here at Country Club Prep we could not be more thrilled! The vintage feel of these jeans brings back an air of classic American preppy style, can you just imagine sitting on a grand sailboat or at a polo match, neck scarf blowing in the breeze, sipping a mint julep, and wearing these jeans? We sure can. Pair these culottes with a kelly green polo and tan sandals for a classic and comfortable preppy outfit


#9 Polished and Professional  

We know what you’re thinking, “Jeans! Polished and Professional? How!” Allow us to explain. It is very well possible to achieve a polished and professional preppy look sans seersucker frock or pleated skirt. When paired with a preppy blouse, tailored blazer, classic pearls, and simple heels, these dark wash Hudson jeans make for a classy and fus free outfit, perfect for dinners or days at the office. Step aside boring khakis!


#10 Classic Black

Achieving the preppy style is all about pairing classic basics together for a timeless look. Having a pair of black jeans on hand to wear with layered polos, flowy blouses, a seersucker blazer, or oxford button down is a must for incorporating denim into your preppy style. This skinny cropped cut will give the appearance of long, lean legs, and is perfect for tucking into your favorite preppy riding boots.

Style Guide

Now that you know the ropes of what to search for in the denim world, allow us to share some tips on styling them to their preppiest potential. Prepare yourself to get a LOT of compliments, you can thank us later.

#1 Casual Everyday

Looking for a more casual and comfortable preppy outfit for your busy life? We are here to help. When paired with basics like a striped button down, simple flats, and gold jewelry, these simple medium wash jeans make for an easy and on the go preppy outfit. Simple preppy style at its finest! From lunch with the ladies, to football practice with the kids, to busy days running errands, this outfit will keep up with you and keep you looking fashionable all at the same time.


#2 Comfy Cozy

Did your ears perk up at the previously mentioned perfect jeans to pair with duck boots on a cold day? It’s okay, we know they did. On a chilly day, jeans are a must for their warmth and comfort, but how you style them makes all the difference. This may be the preppiest gal of all time, and with this guide you very well could be too. At the very first sign of a chill, I.E. when the temperature drops below 70 in the south, pair a dark wash skinny jean with camp socks, duck boots, a gingham button down, and a classic vest for a look that says “preppy” with no if’s, and’s, or but’s.


#3 Preppy & Polished

Now that we have established that it is in fact very possible to look polished and preppy while still wearing blue jeans, let’s go over exactly how to do so. Remember the white, dark wash, and pastel jeans we mentioned before? Pair either of them with a button down oxford, flowy blouse, or striped tee, a navy or black blazer, and fun heels for a look that says yes I’m preppy, yes I’m wearing blue jeans, and yes I look fabulous. Casual Friday has never looked so preppy.


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