As the warmth of summer gives way to the crispness of fall, it’s time to trade in our sundresses and sandals for a wardrobe that embodies the essence of the season. Plaid skirts, cable knit sweaters, and tailored blazers take center stage, layered atop one another to create a look that’s equal parts refined and cozy.
Whether you’re aiming for an Ivy League-inspired aesthetic or a more relaxed, autumnal academia vibe, these preppy fall ensembles will have you looking polished, put-together, and ready to take on the cooler days ahead.
Cable Sweater & Khakis
The quintessential charm of cable-knit sweaters lies in their ability to evoke a bygone era. A staple of preppy style, these cozy pieces are perfect for layering over crisp collared shirts and pairing with pleated trousers to recreate the effortless, 90s-inspired aesthetic of a collegiate fall look.
Navy Sweater & Pleated Skirt
By merging classic prep with a modern twist, this outfit elevates the traditional preppy look to new heights. The crisp white pleated skirt embodies the quintessential charm of a tennis club, yet its pairing with knee-high boots injects a bold dose of ruggedness, making it perfect for braving cooler weather.
Plaid Vest & Khakis
The classic plaid vest is a staple of timeless style, evoking the quintessential charm of old-money enclaves and storied boarding schools. When paired with khaki trousers and a crisp button-down shirt, it forms a failsafe formula for a stylish fall ensemble.
Cardigan & Plaid Skirt
The nostalgic charm of this outfit combination is undeniable, evoking memories of prep schools and the iconic style of characters like Blair Waldorf from Gossip Girl. The white cardigan exudes softness and ease, providing a perfect contrast to the bold, plaid mini skirt. The addition of a headband takes the look to the next level, adding a touch of sophistication and playfulness that’s hard to resist.
Green Sweater & Khakis
A subtle yet striking ensemble has been crafted with the combination of a green sweater and khaki pants. The overall aesthetic is reminiscent of dark academia, with its understated yet impactful vibe. To elevate this look to new heights, incorporate a bold bag and behold – preppy chic has never looked more empowered.
Matching Blazer & Shorts
As the seasons transition from warm to cool, embracing shorts in autumn can be a refreshing twist on traditional fall fashion. Imagine pairing a sleek black blazer with a crisp white shirt, creating a stylish contrast against sheer black leggings. For added texture and a nod to the season’s cozy vibes, slip into chunky loafers that exude a effortless, urban charm.
Blue Shirt & Plaid Pants
A classic combination, plaid and button-downs strike a perfect balance between simplicity and sophistication. The subtle pattern adds visual interest to the outfit, while the crisp collar and well-fitted silhouette evoke a sense of refinement. When paired with a tailored fit and a dash of confidence, this ensemble is more than just a casual affair – it’s a testament to the enduring appeal of heritage prep style.
Sweater Vest & Black Trousers
As the seasons change and autumn’s crisp breeze sets in, sweater vests have officially become a wardrobe staple. And when it comes to mastering the perfect layered look, pairing one with a crisp white collared shirt is an essential move for fall fashion enthusiasts. For those seeking to evoke the timeless charm of academia, this classic combination is the epitome of effortless style.
Tweed Blazer & Mini Skirt
The essence of tweed lies in its effortless sophistication. When paired with crisp white button-downs and mini skirts, the classic fabric takes on a preppy charm reminiscent of iconic American fashion brands like Ralph Lauren. The addition of loafers completes the look, evoking a sense of understated elegance that’s perfect for those who embody the laid-back yet refined spirit of country club culture.
Beige Cardigan & Plaid Pants
A classic combination is born when cardigans meet plaid trousers. The beige knit of the cardigan brings a touch of warmth and coziness, while the structured plaid trousers add a dash of sophistication. To complete the outfit, loafers are the perfect choice, evoking the relaxed yet polished look of a privileged student on autumn break – think Ivy League charm at its finest.
Navy Blazer & Mini Skirt
The quintessential autumnal ensemble is undoubtedly the navy blazer combo. A classic choice, it effortlessly blends preppy charm with modern flair. The subtle contrast of textures – think cable-knit sweater beneath the structured jacket – adds depth to the overall aesthetic, while the mini skirt injects a youthful energy, striking a harmonious balance between timeless and trendy.
Leather Jacket & Pleated Skirt
Where traditional preppy style meets modern urban flair, a harmonious fusion unfolds. Classic elements like the pleated skirt and crisp white shirt provide a timeless foundation, while the oversized leather jacket injects a bold, edgy twist, deftly blending contrasting styles.
Beige Sweater & Mini Skirt
The quintessential combination of classic style and modern flair is achieved by layering a cable-knit sweater over a crisp white shirt, accompanied by a mini skirt that adds a touch of youthful energy to the overall look. This outfit screams ‘academia’ with its effortless elegance, making it perfect for pairing with loafers or brogues for a polished, put-together appearance.
Black Blazer & Grey Sweater
The quintessential 90s prep revival look is effortlessly achieved by combining a black blazer over a gray sweater and a crisp white shirt. This timeless ensemble gains sophistication when paired with comfortable brogues or loafers, making it an ideal choice for embracing the essence of fall.
Navy Jacket & Plaid Skirt
The quintessential combination of plaid skirt and navy jacket effortlessly embodies the epitome of preppy style during the fall season. When paired with loafers, this ensemble exudes an undeniable East Coast charm. And let’s not forget the subtle yet effective addition of socks with loafers – a fashion choice that screams effortless prep-ness.
Cream Knit & Belted Trousers
As the seasons transition into fall, incorporating cream knits with belted trousers creates a light academia-inspired look that effortlessly embodies the cozy atmosphere of the season. The addition of brown accessories subtly ties everything together, resulting in a classic, refined, and quintessentially autumnal ensemble that’s perfect for the changing weather.
Gray Vest & Wide-Leg Trousers
Elevating classic preppy style to new heights, a gray vest paired with a crisp white button-down shirt provides a timeless look. But what truly makes this ensemble stand out is the addition of wide-leg trousers – a bold and confident choice that gives the outfit a powerful, modern twist.
Plaid Skirt & Loafers
The quintessential autumnal ensemble is embodied in this plaid skirt and cable-knit sweater combination. The warm brown hues evoke the crispness of the first week of fall, while the loafers add a preppy touch reminiscent of classic New England style.
Striped Shirt & Sweater Vest
For those looking to create a timeless autumnal ensemble, the humble striped shirt is an excellent starting point. Pair it with a warm brown sweater vest and crisp black tailored pants, and you’ll be rewarded with a polished, effortless look that requires little to no additional embellishments.
Sweater Vest & Mini Skirt
The quintessential autumn look combines a cable-knit sweater with a crisp white shirt, evoking the essence of academia. To add depth to the outfit, pair it with a mini skirt that cleverly balances the layered effect. For footwear, opt for penny loafers or oxfords to bring a touch of sophistication to the overall ensemble. This preppy fall look is versatile and ready to tackle any occasion. Feel free to share your favorite combinations in the comments section below.
