Cool Outfit Ideas for High School Boys



High school is an entirely new phase in the life of a teenage boy. From being on 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 every man’s life – 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 when boys create their personalities, 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 occasionally change, jeans will remain in vogue. Choose a fit that will best suit your body frame. Common jeans 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. They come with a two-color design that makes them smart and flexible for mixing and matching your other outfits. For example, these cool varsity jackets by Varsity Base can be easily paired with jeans, jogger pants, and even shorts. Varsity jackets look great not only on athletic guys but also on any teen boy. They are perfect during schooldays and on regular days, too.

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 a flower, ship sail, tribal prints, abstract, etc., are becoming trendy for teenage boys.

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

Khaki trousers/shorts

High school boys can begin wearing khaki trousers as they transition to being grown-up men. 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. They are perfect for almost any occasion, such as school, church, community, and family events.

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


Teenage boys can’t resist outdoor events, so wearing pants 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 occasion, like shopping, watching movies, or 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!