10 Stylish Winter Outfits for Teenage Guys (With Pictures)

winter outfits for teenage guys

Want some winter outfit inspiration for high school? Here are 10 stylish winter outfits for teenage guys that are actually practical!

Before we get into it, you should note that these outfits really boil down to the fit of the clothing. Without proper fit, you’re sacrificing a big portion of style.

The outfits were picked by color, fit, style, uniqueness, and boldness.

Let’s get into first outfit!

Puffer Jacket and Jeans

winter outfits for teenage guys

A puffer jacket and jeans is one of the best combos for the winter time since it’s stylish and warm.

Puffer jackets are a great addition to your wardrobe essentials. Just make sure that it is high quality and well fitting.

They have a tendency to make people look bigger, but you can use this to your advantage by getting a well fitting one that helps accentuate your muscles.

Consider layering it on top of a well fitting sweater or long sleeve t-shirt and leave the puffer jacket open if the weather allows it.

Double Jacket

Double denim jacket teen style

The double jacket (or jacket over hoodie) combo is one of the toughest winter outfits for teenage guys to pull off. However, it’s also one of the most fashionable things you can do.

If your winter season is still warm, this might not be the outfit for you. If your winters are cool, then definitely give this double jacket look a try!

Make sure the jackets and hoodies are relatively plain. Meaning, don’t wear any with extravagant designs on the front.

Also, the colors of the jackets should coordinate in color very easily. It should look like they were meant to match up together, not like it was forced.

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Fur Hooded Parka Jacket

Fur hooded parka jacket winter outfits men

For all my teenage guys with cold winters, this parka jacket outfits could be a perfect combination between comfortable and stylish.

Pairing the jacket with a great pair of jeans, boots, and sweater really puts this look together nicely.

Notice how the model adds subtle, but different colors to the entire fit and doesn’t use any bright/attention-grabbing colors.

This is a great tip to learn as a teen. Not every outfit has to be flamboyant. Plain and modern colors on your clothing is usually best.

Of course, everyone has their own style, so go with what works best for you!

Flannel and Jeans

flannel and jeans guys

Flannels can be a great add for a pop of color or a touch of pattern to your wardrobe if you’re more of a minimalistic dresser.

Going full winter colors with this one (blues, grays, white, and blacks) is a good idea to match the vibe properly.

Pair this outfit with a good pair of boots to step up your style game even more!

If you don’t have a nice pair of winter boots yet, add it to your list of future clothing purchases.

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Chinos and Hoodie

teen guy wearing chinos and hoodie

Chinos are an excellent alternative for teenage guys who want to switch it up from jeans once in a while.

Pairing chinos with a hoodie makes for a super laid back, young, and stylish look.

Notice how the model above matched his chinos with his beanie. Use this idea as a way to match some of your clothing in the future.

Again, slim fit is what you want to go with, especially if you’re a skinny/muscular teen. Even if you’re a bigger guy, find clothes that aren’t oversized.

Denim Jacket on All Black

Denim jacket outfit for guys

While this may not be one of the most common winter outfits for teenage guys, it is definitely a bold one to be worn on a stylish occasion.

All you need for this is a pair of black jeans, black shoes, a black t-shirt, and a denim jacket.

The attention from this outfit goes directly to the denim jacket, and that’s exactly the point. You want to make the denim jacket to be the head turner in this outfit.

The all black is also excellent for making you look slimmer (that’s the magic of black clothing). Plus, it hides the sweat stains from being noticed if that happens to you.

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Bold Boots

bold boots for men

A bold pair of boots make for a bold statement. The rest of the outfit is not too extravagant (just some well fitting, stylish clothing).

You don’t even have to wear the exact same boots or even the same outfit. The point is to experiment with different colors and putting attention towards certain pieces.

The colors that are being matched on the outfit above are great to copy if you’d like to take inspiration from it and see how you can throw boots into the mix.

Trench Coat

stylish winter outfits for teenage guys

This is one of the most stylish winter outfits for teenage guys if you have the guts to pull it off!

A trench coat in cold weather is one of the hardest looking pieces to add to your outfits. Consider wearing this to a more formal occasion as well!

Trench coats for men look fantastic in black, tan, and gray. Luckily, those are easy colors to match with everything.

The only catch to pulling off this outfit is that everything has to match in quality. Meaning, you need a good pair of jeans, boots, and sweater to work around it.

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All Black Leather Jacket

tom holland winter outfits for teens

This all black leather jacket look is so stylish that it was worn by Tom Holland himself in the winter!

Again, all black is great for looking more slim and pairs well with pretty much anything. Use this to your advantage as a teen.

A leather jacket is also one of the most badass jackets to own as a young guy since it looks edgy and dangerous (not that you actually have to be).

They feel amazing and girls love it. What could possibly go wrong about that?!

Triple Layer Snow Style

triple layer outfits for teenage guys

If you live in a place that snows often, this triple layer style would be great for you!

This outfit is all about layering properly and matching colors well. You can copy this exact style or match simple winter colors to dress without fail.

Consider a great pair of leather gloves to go with the whole look, or dress it up with a fun beanie.

A waterproof jacket is a must since you’re going to get everything soaking wet if you don’t wear one. Rugged boots are a great addition to this outfit as well!


Hopefully these 10 stylish winter outfits for teenage guys have helped you get some inspiration for what to wear to high school or any other winter occasion.

Remember, the key to rocking these outfits boils down to fit and color. Without those 2, the outfits begin to lose their purpose.

If you have any comments, questions, or suggestions leave them down below.

Have fun looking like a badass this fall! 

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