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Men's medium sweatshirts are your go-to for effortless style and comfort. Whether you're hitting the streets or chilling at home, these fresh new styles have got you covered. Discover a variety of on-trend designs that blend functionality with the hottest trends, making it easy to layer up and look good doing it. From classic vibes to modern fits, you'll find the most wanted looks right here, ready to elevate your wardrobe. Dive into our great assortment and get ready to rock your favorite picks with confidence.

$34.99
Now $23.97 (31% Off)

SALE!

An olive oversized crewneck sweatshirt with cuffed sleeves and fleece lining for ultimate comfort.

$49.99
Now $15.97 (68% Off)

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A charcoal crewneck sweatshirt featuring a bold back graphic and cozy fleece lining.

$69.99
Now $22.97 (67% Off)

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A camo crewneck sweatshirt with NASCAR graphics, fleece lining, and cuffed sleeves for men.

$79.99
Now $59.99 (25% Off)

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A multi-colored heavyweight crewneck sweatshirt with bold graphics and a cozy fleece lining.

$59.99
Now $41.97 (30% Off)

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A tan fleece crewneck sweatshirt with a classic embroidered logo and a soft, brushed-back finish.

$74.99
Now $30.97 (59% Off)

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An army green crewneck sweatshirt with a bubble graphic, fleece lining, and cuffed sleeves.

$74.99
Now $30.97 (59% Off)

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A black crewneck sweatshirt with fleece lining, cuffed sleeves, and Obey logo on the front.

$59.99
Now $19.97 (67% Off)

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An oatmeal fleece-lined crewneck sweatshirt with bold graphics and cuffed sleeves, exclusive to Tillys.

$44.99
Now $41.97 (7% Off)

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A black crewneck sweatshirt with chest text, cuffed sleeves, and fleece lining for ultimate comfort.

$109.99
Now $59.97 (45% Off)

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A blue quarter zip sweatshirt featuring New York Knicks applique, stripe details, and a front pouch pocket.

$97.99
Now $59.97 (39% Off)

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A forest green crewneck sweatshirt with a front graphic, relaxed fit, and extra heavyweight fleece.

$44.99
Now $18.97 (58% Off)

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An oversized green cotton crewneck sweatshirt with a faded look and frayed details.

$78.99
Now $49.97 (37% Off)

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A cream crewneck sweatshirt with horizontal stripes, fleece lining, and Guess Jeans emblem on the chest.

$109.99
Now $59.97 (45% Off)

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A black quarter zip sweatshirt with Chicago Bulls applique, stripe details, and team logo embroidery.

$78.99
Now $44.97 (43% Off)

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An off-white crewneck sweatshirt with a relaxed fit, featuring front and back logos and fleece lining.

$109.99
Now $59.97 (45% Off)

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A purple quarter zip sweatshirt featuring Los Angeles Lakers applique, stripe details, and a mock neck.

$64.99
Now $34.97 (46% Off)

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A multi-colored crewneck sweatshirt with large embroidered lettering, made from 90% cotton and 10% polyester.

$69.99
Now $39.97 (43% Off)

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A stone-colored crewneck sweatshirt with front graphic, fleece lining, and cuffed long sleeves.

$78.99
Now $36.97 (53% Off)

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A black cotton crewneck sweatshirt featuring applique and embroidered lettering, with cuffed sleeves and hem.

$44.99
Now $33.97 (24% Off)

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A cream oversized crewneck sweatshirt with allover stripes, made from 100% cotton for ultimate comfort.

$79.99
Now $49.97 (38% Off)

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A black crewneck sweatshirt with racing graphics, fleece lining, and cuffed sleeves for comfort.

$36.99

A white unisex crewneck sweatshirt with a large front graphic, made from a cotton-polyester blend.

$36.99

A white unisex crewneck sweatshirt with a large front graphic, made from 60% polyester and 40% cotton.

$36.99

A light blue, 100% cotton crewneck sweatshirt with a large front graphic and unisex sizing.

Men's Medium Sweatshirts

When it comes to leveling up your everyday fits, men’s medium sweatshirts are the all-season MVP. They’re the go-to layer for just about any occasion—whether you’re catching a late-night skate session, hitting up a backyard hang, or just chilling out after a long day. The beauty of a medium fit is that perfect middle ground: not too loose, not too tight, and always ready to move with you. Picture yourself throwing one on as the sun dips below the horizon during a beach bonfire or grabbing it for those early morning coffee runs when the breeze still lingers. It’s the kind of piece that lives in your rotation year-round, especially when June brings those unpredictable temps—cooler nights, AC-blasted spaces, and road trips where comfort is non-negotiable.

Medium sweatshirts are also a solid pick for gifting. They’re easy to size for most guys and always appreciated, whether it’s a birthday, graduation, or just a low-key “thinking of you” surprise. They suit everyone from the friend who lives in skate parks to the brother who’s always up for a spontaneous adventure. With fabrics that are soft yet substantial, and styles that swing from classic to street-ready, tillys mens sweatshirts are built for layering over tanks or tees, tying around your waist, or tossing in your bag for whatever the day throws your way. The versatility means you can rock them with shorts on breezy summer nights or pair with joggers and denim when the weather calls for extra warmth. And if you’re all about mixing up your look, medium sweatshirts make it easy to switch from beach to street style without missing a beat.

Shopping for the right fit is all about knowing your vibe and how you want to style it. Medium sweatshirts offer that just-right silhouette—roomy enough for comfort, but never bulky. They’re made for layering, whether you’re stacking up for a weekend getaway or just need something easy to throw on between activities. Look for details that match your lifestyle, like ribbed cuffs to keep the chill out, kangaroo pockets for your essentials, or hoods for those unexpected drizzles. And if you find yourself needing a little more room, or you’re into that oversized look, Tillys has you covered with a full range of Large Sweatshirts too. No matter how you wear them, men’s medium sweatshirts are a staple that keeps your style fresh, functional, and always ready for whatever’s next—making them the ultimate layer for every season, every plan, and every moment that matters.