Cool Outfit Ideas for High School Boys

by Adrian J. Elliott | Wednesday, Aug 5, 2020 | 1337 views

High school is an entirely new phase in the life of a teenage boy. From being in their home turf, they’re suddenly transplanted into a new environment. From being the king of their jungle, they’re back as a newbie.

High school years also mark a major transition in the life of every man – and it reflects in their fashion. That’s why choosing the best outfit for high-schoolers can be quite tricky.

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5 Coolest High School Boys’ Wardrobe Pieces

It’s a time when boys begin to create their own personality and fashion is a great way to showcase their unique personal style. Here are five coolest outfit ideas for teen boys.


The most important piece in a gentleman’s wardrobe, jeans are timeless. They never go out of fashion. Although trending colors and fit may change from time to time, jeans will forever stay vogue. Choose a fit that will best suit your body frame. Common types of jean fit are skinny, slim, regular, relaxed and loose. According to, different jeans work for different body types and personalities. For example, skinny teen boys would look well in regular fit jeans, while chubby ones would best wear relaxed jeans. Loose jeans aren’t cool for high school boys. What’s great about jeans is that they are very comfortable to wear and suit the active lifestyle of teenage boys.

Varsity jackets

Another staple in the high school boy’s wardrobe, varsity jackets are very stylish. For example, these cool varsity jackets by Varsity Base can be easily paired up with any jeans, jogger pants and even shorts. They come with a two-color design that makes them very stylish and flexible for mixing and matching with your other outfits. Varsity jackets do not only look great on athletic guys; they look great on any teen boy. They are perfect during schooldays and on regular days too.


When it comes to t-shirts and shirts, teenage boys can stick with their favorite colors. However, it is recommended that you stay away from those with shouting colors or those heavily laden with graphics. Remember, high school teens are not kids anymore. Solid neutral colors look perfect on high school boys, as it makes them look more serious, refined and manly. Choose from the masculine color palette: earth tones, white and pastels, greyscale. White tees with small prints are simple and great too! Lately, tees with overall prints like flower, ship sail, tribal prints, abstract, etc. are becoming trendy for teenage boys too.

Shirts are best worn during formal gatherings. These clothing pieces need ironing so they look great. In some events, you’ll need to wear a tie but not in all. For casual events, polo shirts are suited. They are also the most common types of shirts worn by teenage boys because of their comfort.

Khaki trousers/shorts

As they transition to being grown up men, high school boys can begin wearing khaki trousers. They are perfect for almost any occasion such as events in the school, church or community, as well as on family occasions. Khakis with neutral and earth tone colors look very stylish on teenage boys, and they are also easy to pair up with shirts. Aside from being fashionable, khakis are very light and comfortable to wear.

Shorts are also cool outfit ideas, especially during summer. It offers a nice break from trousers. They look great with printed tees and polo shirts.


Teenage boys can’t resist outdoor events so having pants in their wardrobe is a must. Pants come in different styles, colors, and designs. There are also pants designed for specific athletic events. For instance, track pants are intended for those who love athletics, such as jogging, cycling, skateboarding, etc. Meanwhile, soccer pants are perfect for teens who love football or soccer.

Pants can be worn while teenage boys are engaged in an outdoor event, but they can also be worn for just about any casual event like shopping, watching movies, and going to the park. It is advisable to have different colors and designs for variety.

Fashion Advice

Finally, high school is a great time to showcase your unique personality. Be creative. Be bold. Choose fashion trends that you are comfortable with. Don’t be afraid to wear what you want. Never fall prey to the mainstream fashion trends – they change as fast as they arrive. Stick with the classic gentleman’s wardrobe pieces as they forever remain fashionable and cool!

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