The Coolest Clothing Picks for Tween & Teen Boys

Picking out clothes your tween or teen boy will love can feel like a daunting task, but we're here to make it easy!

Blue Flannel Shirt

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A cozy flannel shirt is a wardrobe staple for any stylish young man. This blue version with double button-pockets and adjustable wrist cuffs is perfect for layering over a t-shirt when he's feeling casual, or under a sweater for a dressier touch. ($25; tillys.com)

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Skinny Stretch Jeans

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These dark denim skinny jeans are perfect for the boy in your life who loves to look nice in his casual wear. Not only are these stylish and versatile, but the stretch material makes these perfect for guys who are constantly on the go. Skateboarding, biking, climbing, or just rough housing with friends? More give in the material means less rips for you to repair or replace. ($30; tillys.com)

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Long Sleeve Henley

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We love the color on this long sleeve casual henley. If getting your teenage boy to dress up a little is a hassle, giving him something comfortable like this is a great option. ($40; tillys.com)

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RED FLANNEL SHIRT

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We've already established that flannel is a classic go-to for building any boy's wardrobe, so this red option should be a no-brainer. Whether your teen boy prefers a preppy look or goes for something grungier, this will fit his needs. ($25; tillys.com)

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Twill Jogger Pants

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Jogger pants are perfect for teenagers who would prefer to wear sweatpants when their dress code requires something a little more formal. This tan pair can be dressed up or down, and the elastic waistband will be a huge hit with any kiddo who puts comfort over style. ($30; tillys.com)

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Windbreaker

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Your kid can still look cool when he's trying to stay warm with this stylish navy windbreaker jacket. The lightweight material is perfect for packing in a bag or leaving in his locker to help combat the wind during chilly months. ($70; tillys.com)

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Oxford Shirt

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Need something to dress your teenager up without making him feel dorky? This charcoal oxford shirt is the perfect compromise. It's nice enough to be worn to special occasions, but comfortable and trendy enough to help him feel confident. ($42; tillys.com)

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Sweater Hoodie

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Would love to get your kiddo in a nice sweater, but you struggle getting him to take off his favorite hoodie? Then this is the shirt for you (or him, rather). This awesome hoodie will keep him toasty warm and as stylish as ever. ($45; tillys.com)

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VANS Sneakers

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Nothing makes a teenage boy happier than a practical, sturdy, classic sneaker—and these high-tops havr all of those covered. They're neutral enough to go with nearly everything, and the retro-feel of this timeless sneaker will score you brownie points with even the pickiest teenager. ($65; tillys.com)

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Pom Beanie

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Who says accessories have to be basic for your teenage boy? Keep his head warm without sacrificing style with this awesome pom-top beanie. ($24; tillys.com)

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