Preppy Looks For Fall


There is an unmistakable chill in the air, and the leaves are beginning to drop. That can only mean one thing...autumn has arrived! Fall is the season of comfort and coziness, and autumn fashion is no exception. Our favorite preppy fall outfits blend tried-and-true staple pieces with on-trend prints and accessories—perfect for hayrides, apple picking, pumpkin carving, and other autumn festivities.

In this preppy style guide, the Prep Obsessed team is sharing our top picks for the season, including newly released autumn styles and cute fall outfit ideas. Get inspired below!

Neutral Turtleneck Sweater

There is nothing more elegant than a neutral-colored turtleneck sweater on a chilly autumn or winter day. Our khaki turtleneck poncho sweater is ultra cozy, and the styling options are virtually endless. One of our all-time favorite fall outfits for women is this turtleneck poncho paired with white jeans and nude booties. Swipe on red lipstick for an effortlessly chic look!

Turtleneck Poncho Sweater Khaki


Buffalo Check

Buffalo check is the unofficial print of autumn—and there are so many ways to style it. A warm buffalo check sherpa vest can be worn over nearly any combination of pants and long-sleeve tops, making it a super versatile piece for your autumn wardrobe. Meanwhile, this striped and buffalo check cardigan combines two of our favorite preppy prints. Looking for something subtle? We are obsessed with these black and white buffalo check earrings!

Buffalo Check Sherpa Vest Black & White


Light Layers

Dressing for autumn can be tricky, since the weather can be warm one day and cold the next. Light, breathable layers are a smart choice for preppy fall fashion, as they can help you stay comfortable and cozy no matter the temperature. Throwing on a navy blue striped wrap is an easy way to make any outfit feel like fall without adding too much warmth. This adorable leopard print poncho will keep your torso toasty, while the short sleeves ensure that you won’t overheat.

Blue Striped Wrap


Cozy Pullovers

A pullover is a timeless autumn staple that will never go out of style. This buffalo check and leopard print reversible pullover can be paired with all of your favorite preppy casual fall outfits. Both chic and comfortable, this quilted plaid pullover is the perfect choice for autumn activities like apple-picking, bonfires, and visits to the pumpkin patch.

Plaid & Quilted Pullover


Oversized Scarves

An oversized scarf is one of our must-have preppy fall essentials. There is just something about a large, chunky sweater that instantly makes any outfit feel cozy and festive. This black plaid fringe scarf is the ideal statement piece to layer over autumn dresses, sweaters, or simple long-sleeve tops.

Plaid Fringe Scarf Black


Belted Dresses Beneath Outerwear

All of those heavy layers can make some outfits appear bulky. Keep your look feminine and sleek this fall by wearing belted dresses beneath your outerwear. This chunky neutral cardigan would look amazing layered over a belted dress in almost any color. Throw on some cute ankle booties, and you’re ready to head out the door.

Puff Sleeve Popcorn Cardigan Mocha


Ankle Boots

Speaking of, ankle boots are our favorite type of preppy fall shoes, because they are guaranteed to go with almost everything in your closet. T-shirt dress and a cardigan? Check! Leggings and a sweater? Check! Mom jeans and a cropped jacket? Check! Kick your fall look up a notch with patterned booties, like these preppy cheetah print ankle boots.

Ankle Boots Cheetah Print

Nature-Inspired Color Palettes 

Not sure which colors to incorporate into your wardrobe this season? Let the shades of nature inspire your preppy fall looks! This mustard military vest is the same color as a bright yellow autumn leaf, while this burgundy balloon sleeve top is reminiscent of freshly harvested apples. Brown, orange, and olive green are beautiful color choices for autumn as well. 

Swiss Dot Balloon Sleeve Top Burgundy


Blazer Over a Patterned Dress

We love fall preppy dresses with bold, eye-catching prints—but sometimes, it’s more fun to let just a pop of pattern show through. For instance, layer a well-fitting black blazer over this leopard print dress for a look that is both stylish and sophisticated. The leopard peeking through the blazer will add playfulness to your look without overwhelming your whole outfit.

Leopard Print Dress With Pockets

The best thing about all of these autumn clothes and accessories? They can be easily mixed and matched to create endless preppy looks for fall. Which preppy fall outfits are you most excited to wear this season?

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  • Corey O'Loughlin
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