Preppy Sweatshirts

Preppy sweatshirts bring a classic, collegiate-inspired look to everyday comfort. With their timeless style and easy versatility, these sweatshirts are perfect for layering on cool mornings, relaxing with friends or adding a pop of personality to your casual wardrobe. Whether you’re heading out for a weekend adventure or enjoying downtime at home, preppy sweatshirts offer lasting value and effortless appeal for any occasion.

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Women's Peaks Island Crewneck
Price was from: $59.95 now: $44.99

A lightweight green crewneck made from 100% French terry cotton, perfect for layering year-round.
Women's Quilted Full-Zip Sweatshirt

A blue quilted full-zip sweatshirt with a brushed cotton interior, mock neckline, and ribbed cuffs.
Men's L.L.Bean Sweater Fleece Pullover
Price was from: $99.95 now: $84.99

A red synthetic fleece pullover with a sweater-knit exterior, brushed interior, and kangaroo pockets.

Pros: Great fit and true to size High quality and well made Warm and suitable for layering Versatile style and color options Very comfortable and cozy
Men's Quilted Sweatshirt, Mockneck

A purple quilted mockneck pullover made from a soft cotton-polyester blend with raglan sleeves and kangaroo pocket.
Men's Quilted Sweatshirt, Crewneck
Price was from: $79.95 now: $64.99

A green quilted crewneck sweatshirt made from soft, brushed cotton-polyester with raglan sleeves for comfort.
Women's Signature Camp Sweatshirt, Crewneck
Price was from: $120 now: $59.99

A slightly fitted, royal red crewneck sweatshirt made from a soft french terry cotton blend.
Adults' Hoodie Sweatshirt
Price was from: $79 now: $54.99

A cozy blue cotton-blend hoodie with ribbed cuffs, kangaroo pocket, and exclusive Freeport-designed logo.
Women's Peaks Island Quarter-Zip Pullover, Stripe
Price was from: $79 now: $64.99

A 100% French terry cotton pullover with rugby-inspired stripes, mockneck, and quarter-zip for cool breezes.
Men's Multisport Lifestyle Sweatshirt, Full-Zip

A blue full-zip sweatshirt made from a soft, durable cotton-recycled polyester blend with zippered pockets.
Men's Bean's Quilted Sweatshirt, Mockneck, Print
Price was from: $99.95 now: $84.99

A brown quilted cotton-blend mockneck sweatshirt featuring a snap placket, kangaroo pocket, and raglan sleeves.
Men's Bean's Quilted Sweatshirt, Crewneck, Print
Price was from: $89.95 now: $74.99

A multi-color cotton-blend crewneck pullover featuring quilted comfort, raglan sleeves, and a heritage logo.
Men's Bold Coast Pullover, Hoodie
Price was from: $89.95 now: $74.99

A softly textured orange hoodie in a durable cotton blend with subtle stripes and an adjustable drawstring hood.
Women's Lakewashed Double-Knit Full-Zip

A versatile sea salt full-zip sweatshirt with a cotton blend, raglan sleeves, and front pockets.
Women's L.L.Bean Cozy Sweatshirt, Full-Zip
Price was from: $89.95 now: $62.99

A red cotton-blend full-zip sweatshirt offering moisture-wicking comfort, UPF 50+ sun protection, and thumbholes.
Men's Comfort Stretch Performance® Piqué, Full-Zip Hoodie, Stripe
Price was from: $89.95 now: $74.99

A blue striped hoodie in a soft, pill-resistant cotton blend with built-in stretch and side pockets.
Men's Multisport Crewneck Sweatshirt

A brown crewneck sweatshirt made from a soft, durable cotton and recycled polyester blend.
Men's Signature Rugged Crewneck Sweatshirt
Price was from: $99 now: $49.99

A slim-fit red crewneck sweatshirt crafted from soft 100% cotton terry cloth with classic logo embroidery.
Men's Quilted Sweatshirt, Mockneck, Stripe

A multi-color quilted pullover with a mockneck, featuring raglan sleeves and a kangaroo pocket.
Men's Sunwashed Sweatshirt, Crewneck

A tan crewneck sweatshirt crafted from a soft, garment-washed cotton blend with a brushed interior.
Women's L.L.Bean 1912 Sweatshirt, Full-Zip Hooded Logo
Price was from: $89.95 now: $62.99

A supersoft white cotton-blend full-zip hoodie with an embroidered logo, kangaroo pockets, and ribbed trim.
Men's Sunwashed Sweatshirt, Full-Zip
Price was from: $89.95 now: $74.99

A red full-zip sweatshirt in soft French terry cotton-poly blend with brushed interior and multiple pockets.
Women's Peaks Island Full-Zip Hoodie

A lightweight pink hoodie in 100% French terry cotton with ribbed details and a full-zip front.
Men's Signature Camp Hoodie Sweatshirt, Print

A tan French terry hoodie featuring exclusive archival graphics, ribbed details, and a chainstitched logo.
Men's Signature Camp Hoodie Sweatshirt

A brown cotton-blend French terry hoodie featuring archival graphics, chainstitched details, and a kangaroo pocket.

Preppy Sweatshirts

There’s something special about slipping into a preppy sweatshirt—the kind that instantly feels like an old favorite, even when it’s brand new. These sweatshirts are rooted in classic style, yet they’re designed for the way you live today: easygoing, practical, and always ready for a little adventure. Whether you’re pulling one on for a brisk morning walk with the dog, a weekend drive along winding back roads, or a cozy evening by the firepit, a preppy sweatshirt brings a sense of comfort and casual polish to every moment. Families love them for their durability and timeless appeal, making them a go-to choice for everything from carpool mornings to campfire nights. They’re also a thoughtful gift for anyone who appreciates quality—college students heading off to campus, friends celebrating milestones, or loved ones who enjoy layering up in style when the temperature dips. With their signature stripes, subtle embroidery, and heritage-inspired details, these sweatshirts blend seamlessly into wardrobes of all ages, inviting everyone to enjoy a little extra warmth and a lot of lasting value.

When choosing a preppy sweatshirt, there are a few things to keep in mind. Look for soft, substantial fabrics that hold up to everyday wear—whether you’re tossing it in your backpack for a day at the lake or reaching for it after a chilly afternoon on the trails. Details like reinforced seams, ribbed cuffs, and sturdy zippers or buttons make a real difference, ensuring your sweatshirt stays comfortable and looking sharp season after season. Many styles are designed with versatility in mind, so they’re just as at home layered over a polo for a backyard barbecue as they are paired with jeans for a casual dinner out. And because preppy sweatshirts often come in a range of colors and patterns, it’s easy to find one that feels just right—whether you prefer bold stripes that pop or understated solids that go with everything. For those who love to mix and match, these sweatshirts pair beautifully with other classic wardrobe staples, including a favorite pair of chinos or even something from our collection of Preppy Dresses.

As January brings crisp air and early sunsets, preppy sweatshirts become essential layers for staying comfortable and looking put-together, no matter what the day brings. Picture a family bundled up for a walk in the woods, each person in their favorite sweatshirt, or friends gathered on the porch with mugs of hot cocoa, sharing stories as the snow falls softly outside. These sweatshirts are made for those moments—reliable, comfortable, and always ready for a little more fun. They’re the kind of wardrobe staple you’ll reach for again and again, year after year, and they only get better with time. Whether you’re shopping for yourself or searching for the perfect gift, a preppy sweatshirt is a thoughtful choice that brings together timeless style, trusted quality, and a genuine love for life’s simple pleasures.

FAQs

Preppy sweatshirts are inspired by classic collegiate and coastal looks, often featuring clean lines, timeless colors, and subtle details like stripes, embroidery, or heritage-inspired accents. These elements bring a polished yet relaxed feel that fits right in at family gatherings, weekend getaways, or casual outings.

Preppy sweatshirts are incredibly versatile. For a casual day, try pairing one with jeans or chinos and your favorite sneakers. If you’re heading somewhere a bit more polished, layer it over a collared shirt or pair it with a classic skirt. These sweatshirts also look great thrown over activewear after a walk or workout.

Absolutely. Many preppy sweatshirts are designed with comfortable, durable fabrics that make them ideal for layering. Wear them over tees or under jackets and vests for extra warmth during chilly months, making them a practical choice for year-round comfort.

Most preppy sweatshirts are made from easy-care materials like cotton or cotton blends. They’re generally machine washable and designed to hold up well to repeated wear and washing, so you can enjoy their comfort and style without any hassle.

A preppy sweatshirt makes a thoughtful gift for anyone who appreciates classic style and lasting comfort. They’re popular with students, parents, outdoor enthusiasts, and anyone who enjoys layering up for everyday adventures or relaxing at home.

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Preppy Sweatshirts