Preppy style is making its return this fall, and we are loving how timeless yet wearable it feels. Inspired by Ralph Lauren’s classic heritage looks, this trend brings together rugby stripes, varsity-inspired layers, cozy knits, and tailored outerwear that work beautifully for the season. What makes it stand out in 2025 is the mix of practicality and polish. It’s just as fitting for running errands as it is for weekend brunches or family gatherings.
We love that these pieces aren’t just passing trends but wardrobe staples that will carry you year after year. Whether you lean into the sporty side with sneakers and caps or the more polished side with loafers and structured bags, this is a style direction that feels versatile, approachable, and perfect for the cozy yet busy rhythm of fall. Here’s how we’re styling preppy looks this season and where you can wear them:
The Trend We're Loving For Fall
Brunch Ready
We love a short-sleeved knit paired with wide-leg trousers. It is easy but feels thoughtful. Add in neutral flats and a blush-toned bag for a soft look that is perfect for brunch or daytime get-togethers. This outfit is great for fall because the wide-leg pants feel relaxed, but the sweater keeps you cozy as the weather cools.
Weekend Casual
This striped rugby with relaxed pink pants and sneakers is such a fun weekend uniform. We love this one for farmers markets, sports games, or casual Saturday plans. It is sporty, playful, and still ties back to the preppy trend with the rugby stripes.
Countryside Classic
This structured jacket with plaid lining is the ultimate preppy fall piece. We love it layered over denim and a crisp shirt for apple picking, family photos, or cozy weekends away. It is practical and warm, but it still gives that elevated Ralph Lauren look we all love.
Pastel Prep
Pastels can work in any season. We love how this pastel cardigan brings a softer take to the trend. Paired with pink trousers and sneakers, it feels fresh but still has that preppy balance. This is great for early fall when you want to nod to the season without going heavy on darker tones.
Varsity-Inspired Layers
Such a cute jacket for fall! We love how a navy bomber instantly brings that collegiate touch to a simple tee and wide-leg denim. Add the burgundy cap for a casual vibe, then swap it for gold hoops if you want to dress it up for dinner. This look is perfect for football games, weekend coffee runs, or even casual Fridays at the office
Classic Rugby Style
This striped rugby top is the definition of preppy style. Layer it under a denim jacket and pair with cream trousers for a look that works for school drop-off, running errands, or grabbing lunch with friends. We love finishing it with burgundy flats and a tote for that classic, pulled-together feel.
Polished Neutrals
We love how a creamy knit under an olive trench coat feels warm, cozy, and sophisticated. Add corduroy pants for texture and tie it all together with a structured neutral bag. This is a great weekday outfit that can take you from morning drop-off to afternoon meetings while keeping you comfortable and stylish.
Heritage Staples
This cable knit layered over a crisp white shirt gives all the Ralph Lauren energy. Pair it with black trousers for a polished base, then add leopard flats to give the outfit personality. We love this one for dinner out, family gatherings, or even a casual date night since it balances classic style with a touch of fun.
Preppy style feels right at home this season and we love how easy it is to adapt. You can go all in with rugbys and varsity details or simply add a cable knit, trench, or plaid-lined jacket to bring the look into your wardrobe. This is a trend that feels classic, wearable, and perfect for layering through the fall months.
Stay stylish,
Tiffany & Tegan
