Men's Oversized Sweaters

Men’s oversized sweaters bring comfort and laid-back style to every day, whether you’re relaxing at home or heading out for a crisp walk. With their relaxed silhouettes and easygoing appeal, these sweaters are designed for layering and versatile wear. Explore a range of timeless colors and classic patterns that make it simple to find the right look for any occasion. Built for lasting value and everyday comfort, men’s oversized sweaters are ready to become favorites in your cool-weather wardrobe.

Sort by:

Filter & Sort

476 Items

Men's L.L.Bean Organic Cotton Waffle Sweater, Rollneck Crew

A cozy tan rollneck sweater made from 100% organic cotton with a thick waffle-stitch knit.

Pros: Soft and warm fabric High quality construction Breathable material Stylish appearance Comfortable fit
Men's Bean's Classic Ragg Wool Sweater, Rollneck

A classic gray rollneck sweater crafted from 100% premium lambswool for warmth and timeless style.
Men's Sunwashed Textured Cotton Sweater, Crewneck

A versatile oyster shell crewneck sweater, 100% cotton with a textured thermal stitch and relaxed fit.
Men's L.L.Bean Classic Ragg Wool Sweater, Cardigan

A midweight charcoal cardigan knit from premium lambswool, offering substantial winter warmth without bulkiness.

Pros: Exceptional warmth Softness High-quality fabric Stylish appearance Comfortable fit
Men's Bean's Heritage Soft Cotton Fisherman Sweater, Crewneck

A richly textured cable-knit sweater made of 100% organic cotton in classic navy, machine washable.

Pros: High quality Perfect fit Softness Warmth Classic look
Men's Wicked Soft Cotton/Cashmere Sweater, Crewneck

A green crewneck sweater in a soft cotton-cashmere blend with raglan sleeves for comfort.

Pros: Great quality Warmth Versatile Comfortable Soft
Men's Katahdin Iron Works® Hooded Sweatshirt, Fleece-Lined

A heavyweight burgundy hooded sweatshirt with fleece lining, cotton blend, and triple-needle stitching for durability.

Pros: Versatile layering piece High quality Perfect fit Available in tall sizes Great warmth
Men's L.L.Bean Sweater Fleece Pullover

A bright navy pullover with a sweater-knit exterior, soft fleece interior, and kangaroo handwarmer pockets.

Pros: Great fit Versatile color options High quality Warm and cozy Comfortable material
Men's L.L.Bean Classic Ragg Wool Sweater, Full-Zip Flannel-Lined

A nautical navy lambswool sweater with a full-zip and warm flannel lining for substantial winter warmth.

Pros: Fit Quality Comfort Warmth Versatility
Men's L.L.Bean Classic Ragg Wool Sweater, Henley

A nautical navy Henley sweater made from 100% premium lambswool for substantial winter warmth.

Pros: High-quality material True to size Stylish appearance Excellent warmth Comfortable fit
Men's Katahdin Iron Works® Hooded Sweatshirt, Flannel-Lined

A flannel-lined, heavyweight hooded sweatshirt with a cotton blend, offering warmth and durability in burgundy or saddle.

Pros: High quality Durable and sturdy Stylish design Warm and cozy Comfortable fit
Men's Bean's Classic Ragg Wool Sweater, Crewneck

A midweight, charcoal crewneck sweater made from 100% premium lambswool, offering substantial warmth without bulk.

Pros: Great fit High quality Comfortable Excellent warmth Classic design
Men's Waterfowl Sweater

A naturally water-repellent merino wool sweater with leather accents, perfect for raw, wet conditions.

Pros: High quality Good color options Stylish appearance Excellent warmth Comfortable fit
Men's L.L.Bean Sweater Fleece Pullover, Print

A green printed pullover featuring premium synthetic fleece, kangaroo pockets, and a soft brushed interior.
Men's Quilted Sweatshirts, Snap Overshirt
Price was from: $99.95 now: $74.99

A dark charcoal heather quilted overshirt combining 80% cotton and 20% polyester with a relaxed traditional fit.

Pros: Comfort Warmth No shrinking Good fit Nice look
Men's Waterfowl Sweater with WINDSTOPPER by GORE-TEX LABS

A brown lambswool sweater featuring windproof, breathable WINDSTOPPER fabric and durable shooting patches.

Pros: Classic, good-looking style Durable, high-quality fabric True to size and great fit Comfortable and soft lining Warm and windproof
Men's Bean's Classic Ragg Wool Sweater, Crewneck, Bird's-Eye

A midweight lambswool sweater in a timeless bird's-eye pattern, offering substantial warmth without bulk.

Pros: Stylish design Warmth Softness Quality material Comfortable fit
Men's Organic Cotton Waffle Sweater, Rollneck Crew, Stripe
Price was from: $99.95 now: $79.99

A rugged green crewneck sweater crafted from 100% organic cotton with a thick waffle-knit texture.

Pros: Great fit Handsome appearance Ideal for cool weather Warm and cozy Comfortable to wear
Adults' Bean's Classic Fleece Pullover
Price was from: $79.95 now: $63.99

A rustic green, oversized unisex fleece pullover made from 100% recycled polyester with a snap front and high collar.
Men's L.L.Bean Organic Cotton Waffle Sweater, Henley

A cozy tan henley sweater crafted from thick, waffle-knit organic cotton with ribbed trim and four-button styling.
Adults' Bean's Classic Fleece Pullover, Print
Price was from: $79.95 now: $63.99

An oversized, multi-color unisex fleece pullover made from soft, 100% recycled polyester with classic 1990s details.
Men's Sunwashed Textured Cotton Sweater, Crewneck, Stripe
Price was from: $79.95 now: $67.99

A brown 100% cotton crewneck sweater with a textured thermal knit and relaxed, weathered look.

Men's Oversized Sweaters

When the air turns crisp and the days grow shorter, there’s nothing quite like pulling on a well-made, oversized sweater. Men’s oversized sweaters have become a favorite for anyone who craves comfort, warmth, and easygoing style all winter long. Whether you’re heading out for a weekend hike, gathering around a backyard fire pit, or simply relaxing indoors with family, these sweaters offer a timeless way to stay cozy without sacrificing freedom of movement. The relaxed fit of baggy jumpers for men makes them a practical choice for layering, allowing you to throw one over a flannel shirt or thermal base layer as temperatures drop. Their generous cut is not just about comfort—it’s about versatility, too. You can wear them with jeans for a casual outing, or pair them with rugged outdoor pants for a day spent exploring the woods. Oversized sweaters have a way of making chilly mornings and frosty evenings feel a little more inviting, wrapping you in warmth that lasts season after season.

Men’s baggy sweaters aren’t just a smart addition to your own winter wardrobe—they also make thoughtful gifts for the men in your life. Whether you’re shopping for a college student who’s settling into dorm life, a friend who loves spending weekends at the cabin, or a family member who enjoys classic, comfortable style, these sweaters are sure to be appreciated. The appeal lies in their easy fit and enduring quality. Baggy sweaters mens styles are designed to accommodate a range of body types and preferences, so you can feel confident giving one as a gift without worrying about finding the perfect fit. Plus, the timeless look of mens baggy jumpers means they’ll never go out of style, making them a reliable favorite year after year. Picture a snowy December afternoon: you’re sipping hot cocoa, the fireplace crackling nearby, and you’re wrapped in the familiar softness of an oversized sweater. It’s a simple pleasure, but one that brings warmth and comfort when it’s needed most.

When choosing men’s oversized sweaters, look for features that promise lasting value and everyday ease. Durable fabrics, reinforced seams, and classic designs ensure these sweaters can handle everything from a brisk morning walk to a spontaneous snowball fight. Many styles are crafted with comfort in mind, offering soft, itch-free textures and ribbed cuffs that keep the cold at bay. The best mens baggy sweaters are easy to care for, so you can spend less time worrying about upkeep and more time enjoying the great outdoors—or a well-deserved day off. If you’re looking for even more options in generous sizing, be sure to browse our selection of Large Men's Sweaters to find the right fit for you or someone special. With the right oversized sweater, winter’s chill feels a little less daunting, and every day is an invitation to step outside and make the most of the season.