A Man For All Seasons: 100 Cool Outfits For Teenage Guys For Every Season

When it comes to finding the perfect outfit, teenage guys can be particularly hard to please!

A Man For All Seasons: 100 Cool Outfits For Teenage Guys For Every Season

However, there are plenty of stylish, comfortable, and easy-to-put-together outfits for teenage boys that can fit every season. 

With this in mind, we are going to be taking a look at 100 of these outfits in particular.

We are going to be doing this by splitting up these outfit ideas across all four seasons: spring, summer, fall, and winter.

We will take a look at 25 outfits for each season so that any teenage guy can truly become a man for all seasons! Let’s get started. 

Spring Outfits- March, April, And May

  1. Long Sleeved Shirts With Shorts

When springtime rolls around, it’s time to get out the shorts and start preparing for warmer weather.

Wearing long sleeves allows for some protection should you be dealing with rain, whilst the shorts let in some breeze. 

  1. Long Sleeves With Chinos

If it is too cool for shorts, opt for a pair of chinos with a long sleeved tee instead. 

  1. Graphic T-Shirts And Ripped Jeans

Graphic t-shirts and ripped jeans are every teenager’s best friend, so combining them makes for a stylish outfit brimming with personality. 

  1. Bomber Jacket With A T-Shirt And Chinos 

Spring is a time when the weather can fluctuate between mild, warm and sometimes a little chilly.

On days with some bite- but enough warmth to make it too hot for jeans-, a bomber jacket over a pair of chinos with a simple shirt is a stylish, teen friendly option.

  1. Sweats With A Jacket

We all know that teens are prone to wearing sweats all day, every day, and the spring is a great time to do so thanks to the mild weather.

Add a jacket, over the top of comfy sweats, for some warmth and style on a cooler spring day. 

  1. Floral Shirts With Cropped Jeans

When the weather starts to get warmer, break out the floral shirt! To avoid the awkward dad look, teens can opt for some cropped jeans.

  1. Flannel Shirt With Hoodie

A flannel shirt is a staple in any guy’s wardrobe- no matter what their age- but if the springtime weather gets cold, pair one with a hoodie underneath for some fashionable layering and warmth. 

  1. Black And White

Monochromatic color schemes are a great way to make a sophisticated fashion statement, and the same can be said for a teenage guy’s wardrobe. 

  1. Denim On Denim

Denim on denim isn’t for everyone, but for teen guys it can become a cool and eye-catching outfit that fits the spring weather perfectly.

  1. Shorts With A Denim Button Up

Whilst we are on the subject of denim, a denim button up shirt can be a comfortable yet fashionable choice for the spring weather.

Pair them with some shorts to stay cool whilst looking stylish.

  1. Short Sleeved Flannels

For those warmer spring days, short-sleeved flannel shirts are a great option for teens, as they can go with pretty much anything.

Throw one over a pair of jeans, shorts or even chinos, and you’re ready to go.

  1. Cargo Pants And Crew Neck Sweaters

Sweaters are best kept for cooler spring days, and one young and fresh way to style a crew neck sweater is to pair them with some comfortable and versatile cargo pants to combine both style and practicality. 

  1. Colorful Vests

Whether it’s a puffer jacket vest for the cooler spring days or a thinner vest for warm days, bright colors can bring some life into any wardrobe.

More vibrant colors can add a fun and youthful look.

  1. Cut Off Denim Jeans

Cut off are becoming more and more popular with young men thanks to their stylish look and comfortable fit.

Although they are suitable for all seasons, cut off denim jeans can work wonders during the springtime for a teenager.

  1. Statement Cardigans

Cardigans are a must-have in any wardrobe as they are perfect for popping over the top of any outfit when things get chilly.

On a rainy or cold spring day, teenage guys can get a lot out of a statement cardigan with patterns or block colors.

  1. Block Sweaters With Matching Trousers

Similar to cardigans, sweaters are a great choice for the cooler spring days.

Block sweaters can be eye catching, and matching trousers only elevate the stylish nature of a well-chosen block sweater.

Perfect for teen boys looking for something different from their lightweight knitwear. 

  1. Sweatshirts And Shorts

Warm and comfortable sweatshirts work well with shorts during the springtime when the weather is being unpredictable.

This casual look is a frequent one amongst teenage guys, as is anything that involves sweats in any way!

  1. Striped Shirts With Jeans

Whether it is a button down shirt, a plain tee or a long sleeve shirt, stripes are a fashionable addition to any guy’s wardrobe, including teens.

Pair a button down striped shirt with ripped jeans for a spring smart casual look, or a striped tee with some chinos to keep cool in warmer spring weather. 

A Man For All Seasons: 100 Cool Outfits For Teenage Guys For Every Season
  1. Spring Layering

Layering is great for most seasons (except for the hotter summer weather) and in the springtime, layering jackets with hoodies or flannel shirts with plain tees can make for a stylish yet youthful outfit that not only suits the spring weather, but is also well suited to teenagers.

  1. Blazers And Brightly Colored Shirts

Blazers can be the perfect addition to any man’s outfit to add some smart casual flair. For teens, blazers can add some personality and style.

Pairing a blazer with a graphic t-shirt or any kind of brightly colored shirt can make for a unique- yet still young and vibrant- spring outfit.

  1. Ripped Jeans And Hoodies

You can never go wrong with a pair of ripped jeans and a comfortable hoodie, especially for teenage boys who might want to just grab the first thing to fall out of their wardrobe. 

  1. Light Trench Coats

For those cooler spring days, a light trench coat can offer some stylish protection whilst not risking overheating should the weather get warmer throughout the day. 

  1. Polo Shirts

Great for both spring and summer- as well as fall and winter when layered- polo shirts are a cool and fashionable way for teenage guys to stay cool and comfortable on hotter spring days. 

  1. Bright And Baggy Rain Coats 

Spring can often be a particularly rainy season, so it’s useful to have a raincoat spare in your wardrobe to prepare.

There are all sorts of raincoats available, including bright colors and different patterns.

  1. Button Down Shirts And Khaki Shorts

Perfect for both the spring and summer weather, button down shirts and khaki shorts are the epitome of fashion for teenage guys when the weather starts to warm up. 

Summer Outfits- June, July, August

  1. Denim Shirts With Chinos

When the summer rolls around, it is important to beat the heat by keeping layers thin and clothes breathable.

Buttoned denim shirts are a breezy option, whilst chinos offer an alternative to shorts that is still guaranteed to keep you cool.

  1. Short Sleeves And Chinos

In the same manner, short-sleeved shirts can be paired with chinos for a summery teenage look too. 

  1. Printed Shirts With Shorts

From band t-shirts to graphic shirts, summer is the best time to whip out any printed shirts and combine them with shorts for an individual look. 

  1. Floral Shirts With Shorts And Hats

If you’re more of a floral shirt kind of guy, summer is just as perfect for rocking that flower print or that Hawaiian shirt.

Pair them with shorts and a straw hat with flip-flops to nail that vacation look.

  1. Floral Shirts With Ripped Jeans

Floral shirts aren’t just for the super hot summer weather, though. When the summer is a little milder, you can also pair one up with ripped jeans.

  1. Sleeveless Shirts

When the weather gets hot, sleeveless shirts and vests can be lifesavers. They come in a wide range of colors and styles, making them a versatile choice in a teen’s wardrobe too.

  1. Vibrancy That Stays Cool

As long as what you are wearing keeps you cool, it’s sure to suit a teenager’s summer wardrobe. Vibrant colors can add a dose of youth to a teen boy’s summer outfits. 

  1. Patterned Shorts With Button Ups

If regular shorts are a little too plain, opt for some patterned ones with a button-up shirt for something a little different. 

  1. Shorts, T-Shirts, And Baseball Caps

The All-American baseball cap can do a lot to spice up a plain summer shorts and t-shirt combo. 

  1. Sweat Shorts And T-Shirts

Much like the usual shorts and t-shirts, sweat shorts are a comfortable and convenient summer option for teens that can become a stylish one too given the different styles of sweat shorts available.

  1. Blue And White

Blue and white color schemes are wonderfully summery, evoking a nautical, contemporary vibe.

Blue and white color schemes can make for a stylish addition to a teen boy’s wardrobe. 

  1. Breathable Layers

Layers aren’t always best suited for summer, but they can work wonders for both style and comfort, so long as what you are layering is made with a breathable material, such as linen or cotton.

  1. Colorful Chinos With White Shirts

Different colors of chinos with plain white shirts can make for a mature and stylish look for a teen. 

  1. Flannel Shirts And Shorts

The old reliable flannel shirt is a must in the summer, especially when paired with a comfortable pair of shorts. 

  1. Striped Polo Shirts

We mentioned polo shirts before for the springtime, but there is something about the striped polo shirt that feels very summery, making for a cool and comforting summer wardrobe addition.

  1. Shorts And Vests

When all else fails, teens and adults alike can trust a pair of shorts and a vest to help beat the heat. 

  1. Denim Shirt With Shorts 

Much like with chinos, denim shirts also work well with shorts for a stylish yet comfortable teenage summer look. 

A Man For All Seasons: 100 Cool Outfits For Teenage Guys For Every Season
  1. Lightweight Jackets

Jackets are a necessity for summer nights when the temperature can drop, but make sure to keep them lightweight so that you can make use of them during cooler summer days too. 

  1. Pastel Shades

Nothing says summer more than pastel shades, whether it is a polo shirt, a pair of shoes or a simple t-shirt. 

  1. Summer Stripes

Much like polo shirts, stripes ooze of summer fashion and this goes for the summer wardrobe of teen guys too.  

  1. White Trousers

Teens willing to take the plunge with white trousers during the summer are sure to reap both style and comfort benefits.

Just make sure they don’t get too dirty or mom and/or dad will not be happy with the extra laundry! 

  1. Suede Jackets

Suede is an underutilized material, often thought to be delegated to older adults only, but this is far from the case.

Suede jackets could be just the stylish and lightweight summer jacket you’ve been waiting for. 

  1. Sweat Shorts And Buttons Ups

Get the best of both the super casual and the smart casual with a combo of sweat shorts and a button up. 

  1. Linen Shirts

Linen is a very breathable and cool shirt material, making it perfect for the summer.

Teens can mix and match with linen too thanks to its versatility and the range of colors and styles that you can get them in. 

  1. Tie Dye

Go full on hippie chic with a tie-dye shirt! Combine it with a pair of shorts and flip-flops to get the ultimate relaxed teen look.

Fall Outfits- September, October, November

  1. Sherpa Jackets And Turtlenecks

Once the weather starts to cool down, a good jacket is imperative.

Sherpa jackets are perfect for particularly cold autumn days and when paired with a turtleneck sweater, they can make for a modern teen outfit. 

  1. Sweats With Hoodies

You just can’t beat being comfortable in the cooler weather, so sweatpants with a hoodie is sure to be a go to for a teen guy in the fall.

  1. Sweatshirts And Jeans

Mix it up by combining sweats with jeans to stay comfortable yet casual in the autumn. 

  1. Flannel Shirts With Jeans

Fall is the perfect time for the classical jeans and flannel shirt look, thanks to the season maintaining a good balance between the heat and the cold.

You can also easily adapt the flannel and jeans look if it does get too hot or too cold. 

  1. Sherpa Jacket With Plain T-Shirt

When it’s not cold enough for both a sweater and a jacket, but still cold enough for a jacket, a Sherpa jacket with a plain shirt will keep off the chill without making you overheated. 

  1. Double Jackets

The importance of layering cannot be understated and when the cooler months roll around, it is the perfect time to start layering shirts as well as jackets for warm and stylish looks. 

  1. Rugged And Warm Fall Tones

Fall has a great selection of tones and colors in its palettes- from burnt oranges to peach to cream and more- so teens willing to make use of them are sure to make an individual statement in their wardrobe. 

  1. Sweater With Chinos

Much like how chinos and shirts are fantastic for summer, pairing chinos with sweaters is a great option for the cooler months that begin to take over in the fall.

  1. Triple Layers

If double layers aren’t enough, teens can try triple layering to stay warm whilst looking awesome, such as by layering a t-shirt with a flannel shirt followed by a Sherpa jacket over the top. 

  1. Hoodie With Denim Jacket

Hoodies are every teenagers best friend, and this becomes even more so in the fall and winter.

Double layer a hoodie with a denim jacket to add a touch of rustic style. 

  1. Hoodie With Leather Jacket

Not into denim? A leather jacket can work just as well when double layered up with a hoodie. 

  1. Hoodie With Baseball Jacket

If it is as an All-American boy look that you are going for, a hoodie layered with a baseball jacket or a varsity jacket can work wonders in terms of style and comfort. 

  1. Neutral Sweaters

Like hoodies- but a little less bulky- sweaters can become a lifeline in cold months. Utilizing sweaters with neutral colors and tones allows for more opportunities for layering.

  1. Denim Button Downs

A lone denim button down can be enough for a milder autumn day, but you could also choose to partner it with a jacket if you need to. 

  1. Oversized Flannel Shirts

Oversized flannel shirts can be just as stylish and comfortable as regular ones (sometimes even more so compared to form fitting flannels!).

They can act as standalone shirts or even as jackets if they are big enough. 

  1. Overcoats

When the fall weather is chilly- but still mild enough to keep the bigger coats at bay- a simple, thin overcoat with a t-shirt can be a stylish and practical choice for a teen.

  1. Colorful Jackets

Autumn officially marks the beginning of jacket season, and teenagers can make it their own by opting for a jacket that is colorful and unique to their personal tastes. 

A Man For All Seasons: 100 Cool Outfits For Teenage Guys For Every Season
  1. Knitwear

Knitwear is sure to be a go to for many teenage guys come the fall, particularly knits such as cable knits, otherwise known as a Fishermans Knit Sweater. 

  1. Turtleneck

We briefly touched on turtlenecks earlier, but they are easily able to be worn alone as well as part of an ensemble for warmth and style during fall. 

  1. Puffer Jackets

You might think puffer jackets are relegated to winter only, but they can easily keep off the chill during fall.

You could also wear a sleeveless puffer vest when the weather is a little milder. 

  1. Pea Coats

These are also a great choice for both fall and winter, thanks to their sturdy nature and being double-breasted.

In the fall, they are best used with a shirt, as they can get quite warm. 

  1. Sports Jackets

Similar to a blazer, a sports jacket can be paired with a sweater of any kind for a smarter fall look. 

  1. Quilted Jackets

For something a little more youthful than a peacoat and sports jacket, a quilt jacket is the perfect choice. 

  1. Chinos And Knitwear

Chinos and knitted sweaters- or any knitwear in general- can create a cute, preppy style for teenage boys in the autumn. 

  1. Beanie Hats

For an accessory that is hugely versatile as well as practical in the colder months, a beanie hat is the perfect choice for a teen as well as adults. 

Winter Outfits- December, January, February

  1. Cropped Pants With A Leather Jacket

Even in the coldest winters, cropped pants are sure to be a stylish and comfortable fashion choice.

To avoid getting cold, they are best worn with boots that will keep the ankles good and covered!

Pair them with a leather jacket to get a slightly punk look.

  1. Puffer Jacket With Jeans

As mentioned, puffer jackets are perfect for cold weather. In the winter, they are a comfortable and fashionable option that can easily pair with all kinds of jeans. 

  1. Chinos With Hoodie

Just because the weather is colder doesnt mean you cant rock a pair of chino and stay warm doing it!

Pair them up with a hoodie for a cool smart casual combo. 

  1. All Black With Denim Jacket

All black is a super fashionable look that lots of teens like to engage in, and the winter is the perfect time to do so as you can avoid getting overheated.

Toss a denim jacket over the top for some added warmth and style, black to maintain that all black theme or blue to mix it up a little. 

  1. Thick Trench Coats

We talked about trench coats earlier and the same still applies in the winter.

Just make sure to invest in a thicker one for the cold and jazz it up a bit with a beanie and some leather gloves. 

  1. Leather Jackets With Boots

Leather is great for locking in warmth and looking stylish whilst doing it.

For a biker/grunge vibe, consider teaming up a leather jacket with some boots. 

  1. Fur Hooded Parka Jacket

This is the perfect jacket for teens in the winter moths thanks to the practicality of the parka combined with the modern styling of the furry hood. 

  1. Patterned Pullovers And Jeans

The winter is a great time to start mixing and matching patterns and colors, and teens can do so with sweaters and pullovers to ensure that they stay warm. 

  1. Blazers With Hoodie

Fans of the smart casual look can maintain it throughout the winter months by pairing a thick hoodie with a blazer.

If your hoodie is particularly thick, you might need to opt for a blazer that is a few sizes bigger than what you normally wear. 

A Man For All Seasons: 100 Cool Outfits For Teenage Guys For Every Season
  1. Textured Cardigans

We mentioned cardigans earlier, but textured ones offer an extra layer for the colder months as well as some depth in terms of their design.

  1. Chunky Sweaters

One of the favorite forms of knitwear when the weather gets cold is the chunky sweater, and teenage guys can easily incorporate it into their winter wardrobe.

Pair them with a leather or denim jacket and boots for a comfortable winter look. 

  1. Thick And Warm Knitwear 

Knitwear showed up a little earlier on this list, but the importance of utilizing the thickest and warmest knits during the winter shouldnt be underestimated! 

  1. Colorful Scarves

Scarves are practical winter accessory, but they can also be an fashionable style choice thanks to the wide range of colors, patterns and styles that are available.

They are a must for every teen boys winter wardrobe. 

  1. Combat Boots With Leather Jacket

Some teenagers are fond of a more military style of fashion and the winter is a great month to bring this to the fore with items such as leather jackets, combat boots, or military jackets. 

  1. Columbia Coats

Columbia coats are perfect for extreme weather- such as rain or snow- as well as for keeping warm thanks to being insulated.

They are practical coats, able to be adjusted and with a stowaway hood attached.

Whilst some might not find them as fashionable as some other choices, you can definitely pair it with various accessories to jazz it up. 

  1. Bomber Jackets

Also known as flight jackets, bomber jackets might have originated in the 1950s, but it is considered a fashionable and modern jacket that many teenagers and young adults have embraced.

The thick sheepskin lining makes for extra warmth and comfort in the winter. 

  1. Corduroy Pants

Corduroy is a fabric that is particularly thick and stylish, as well as an alternative to regular pants or jeans.

They are also available in a wide range of colors, making them particularly versatile. 

  1. Duffle Coat

Duffle coats are also a great choice for a winter coat for teens as they can easily be paired with sweaters, button ups and long sleeved shirts. 

  1. Sweaters With Jeans And Beanie Hats

If you are a fan of the simpler wardrobe style, it is easy to stay warm and comfortable in the winter with a simple sweater and jeans combo paired up with a beanie hat and some gloves for extra style.

  1. Military Jackets

Created to keep the wearer protected from the elements, military jackets have become very popular with teens and young adults, similar to bomber jackets.

They are also a highly fashionable as well as practical thanks to their built-in insulation. 

  1. Woolen Overcoat

The epitome of warmth and comfort when it gets very cold, long, woolen overcoats are incredibly stylish and practical, as well as versatile enough to be worn with a variety of clothes, such as sweaters or button ups. 

  1. Wool Pants With Sneakers

If warmth is your top priority, a pair of wool pants with some sneakers and a sweater can be a thoroughly modern addition to any teen’s wardrobe. 

  1. Lots Of Layering 

Layering is incredibly important when the winter rolls around, so make sure that you have plenty of options when it comes to double or triple layering so that you can stay nice and toasty. 

  1. Thick Sweats With Boots

As we have said, you just can’t beat a nice, comfortable pair of sweats, and the winter months are no exception.

Layer up your sweaters and pair them with some boots for some comfortable warmth. 

  1. Classic Hoodie With Jeans And Winter Boots

Last but not least, a regular hoodie with some jeans and warm winter boots- such as combat boots, winter boots or leather boots- can be a simple yet stylish choice in any teen guy’s winter wear wardrobe. 

Final Thoughts

So there you have 100 ideas for a teen guy’s wardrobe, with options that can be worn throughout the four seasons!

Whether you are a teenager looking to add some new inclusions to your wardrobe, or are the parent or guardian of a teen boy looking for ideas, hopefully you will have found something here that will be suitable. 

Joseph Pais