Boys’ Holiday Outfits: How To Dress Your Little Ones For The Festivities

When it comes to dressing up boys for the holidays, the challenge is finding outfits that are stylish, comfortable, and easy to put together. Whether your little one prefers a preppy look or loves sportswear and can’t imagine ditching his sweats, we’ve got you covered with our recommendations on the key clothing items that can be mixed and layered to suit every personality. Here’s your ultimate guide to creating cute holiday outfits for boys using versatile essential pieces and a simple dressing formula.

 

1. Sweaters

Cozy knits in seasonal colors like red, green, or cream are a great base and can add a festive touch to a simple outfit. Top a sweater over a polo or button-down for a polished dressier look. If that feels a bit stiff for your boy, an oversized sweater over a tee can be a great compromise.

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2. Blazers

Add instant polish with a tailored blazer. Tweed, corduroy, or velvet textures scream holiday chic! For the sporty guy, try topping a monochrome sweat set with a blazer for a comfortable dressed up look.  If he prefers a more casual vibe, a simple t-shirt or crewneck sweater is an easy alternative for a fun and festive vibe.

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3. Oxford Button-Downs

Button-downs are a perfect foundation for layering.  We recommend a button-down shirt under a festive sweater for a classic look. For the boy who prefers comfort, on the other hand, allow him to wear his button-down open and untucked under a solid tee and paired with his favorite pants.

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4. Prints And Plaids

A festive touch of plaid is a favorite for the season. Whether worn on a top or trousers, plaid always adds that classic holiday charm. We love plaid flannels for a perfect winter closet staple that your boys will wear well beyond the holidays.

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5. Wool Coats

It’s amazing how quickly an outfit can be elevated with the right piece of outerwear. Even the boy who refuses to dress up can shine in a structured wool coat. Keep the look monochromatic underneath for a modern, sleek and simple base. 

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With these easy outfit formulas, your boy will look festive without compromising on comfort. Keep the vibe fun and stress-free by mixing his favorite pieces with holiday touches. Whether he’s channeling preppy sophistication, sporty cool, or cozy comfort, he’ll be ready to shine in every family photo!

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Erin Eagle

Founder & digital stylist at A Style Set

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A Guide To cute holiday outfits for girls