Preppy Jeans Outfit Ideas

Jeans are the ultimate style staple. Whether you are curating a minimalist capsule wardrobe or are all about experimenting with the newest trends, jeans deserve a spot in your closet.


While it’s true that jeans go with just about everything, it’s always a good idea to stay on top of current jean trends to inspire your preppy jeans outfit ideas. Keep reading to discover our favorite trending jeans and how to style them for cute preppy looks.

1. Dark Wash Jeans with a White Button Down

Dark wash denim plus a crisp white button down? Talk about timeless! Pairing these two wardrobe staples together is an easy, effortless way to look polished and stylish. The Reba jeans are the perfect choice for nailing this look; they feature a high-rise relaxed fit, five pocket cut, and an ankle length silhouette, all shaped from stretchy dark wash denim. Finish off the look with a pair of loafers or pointed flats.

 Hi-Rise Relaxed Fit Jeans

2. Wide-Leg Jeans with a Chic Blazer

Jeans and blazers are yet another classic pairing — but that doesn’t mean this look can’t also feel fresh and on-trend. One of the hottest women's jean trends of the moment is wide-leg jeans, like these super cute Olivia wide-leg cropped jeans. Style them with an oversized plaid blazer and heels for a modern twist on a quintessentially preppy look.

Wide Leg Cropped Jeans

3. White Jeans with a Striped Top

White denim and stripes are a preppy match made in heaven. Whether you are styling them with a classic blue and white striped boat neck tee or a colorful striped blouse, white jeans are the perfect choice for balancing out a striped top. Opt for these high-waisted white skinny jeans for a super flattering fit, or make the most of new jeans trends with these mid-rise boyfriend white jeans.

Mid-Rise Boyfriend White Destroyed Jeans

4. Flare Jeggings with a Sweater

Hello, cute autumn style! We love the look of high-rise flare jeans styled with a cute sweater, and this pair is especially nice because of the stretchy pull-on fit. Tuck in your sweater and finish off with a belt for a timeless preppy look, or let the sweater hang loose and add a floppy hat and layered necklaces. Either way, you can’t go wrong with this style for fall and winter.

High Rise Flare Jeggings

5. Distressed Jeans with a Relaxed Jacket

Distressed denim is a year-round staple, but it pairs especially well with relaxed outerwear for autumn and winter. These preppy skinny jeans feature a unique twist: the distressing is accented with peek-a-boo buffalo plaid patches, making them the perfect piece for those chilly months of the year. Style them with a sweater or long-sleeve top and a relaxed jacket for a casual preppy look that will keep you warm and cozy.

Blue Skinny Jeans with Plaid Peek-a-Boo Patches

6. Boyfriend Jeans with a Sweater Vest

Sweater vests are having a major moment right now, and we love their old-school prep vibes. Keep things on-trend by layering a preppy sweater vest over a white button down, and finishing off the look with a pair of flattering light wash boyfriend jeans. Too warm for long sleeves? Opt for a white tee instead. Cute, comfortable, and preppy? Yes please!

Mid-Rise Destroyed Hem Boyfriend Jeans


We hope you’re loving these preppy outfits with jeans as much as we are! Which jean trends and looks are you wearing this season? Be sure to share with us on social media @prepobsessed.


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