How to Dress Cool for Middle School (Boys)

Co-authored by Veronica Tharmalingam and Amy Bobinger

Last Updated: February 28, 2023 References

Going to middle school is like entering a whole new world. You go from being the top of the food chain in elementary school to suddenly being surrounded by cool older kids with a killer fashion sense. If you’re a boy in middle school, you can dress cooler by finding your own personal style and adding pieces to your wardrobe until you get the look you want.

Method 1

Method 1 of 4:

Finding Your Own Style

1
Pay attention to what other people are wearing. You don’t want to exactly copy anyone else’s style, but you should pay attention to what other people are wearing. What styles are you most drawn to? Once you start paying attention to what you like, you’ll know whether you are more into a crisp preppy look or if you favor a more laid-back street-style vibe. Identifying your style can help you be more fashionable.^{[1]
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2
Know what looks good on your body type. If you’re slender, you might want to wear horizontal stripes and dress in lighter colors to make you look more muscular. If you’re broad across the middle, dark colors can make you appear slimmer, and a belt will make your waist appear smaller. If you have an athletic body type, wear slim-fitting shirts and straight-leg jeans to show off your muscular figure. If you have an "average" build, you can wear almost anything — just avoid loose or saggy clothing.^{[2]
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3
Find inspiration in magazines and online. Check out fashion magazines, style blogs, Pinterest boards, and pictures of celebrities to get ideas of the kind of style you’re into. Remember that you’ll be wearing these looks to class, so look for styles that are appropriate for school. George Clooney might look great in a tuxedo, but it might not be the right outfit for history class.^{[3]
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4
Be willing to experiment. Sometimes the only way to know if something looks good on you is just to wear it. You might be all about the skater vibe, only to discover that you don’t like the way it looks on you. On the other hand, that shirt that your aunt got you might not seem like your style at first, but it could grow to become your favorite after you pair it with the perfect jeans. Middle school is all about finding yourself, so don’t be afraid to experiment with your look.^{[4]
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5
Don’t fall victim to trends. You should know the difference between what you really like and what’s a trend right now. Think about looks from previous decades that look really dated. You probably wouldn’t wear wide-legged skater jeans from the 90s, or cut your hair in a mullet in the 80s today. Classic pieces like well-fitting jeans and button-down shirts or t-shirts are always in style.^{[5]
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Method 2

Method 2 of 4:

Creating a Basic Wardrobe

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Buy jeans that fit you well. You probably already have a couple of pairs of jeans, but you might not like how they look. Focus on finding at least 2 pairs of jeans that fit you comfortably in the waist and which are just long enough to brush the tops of your shoes. If you have a pair that you like but which are a little too long, ask a family member who knows how to sew to hem the pants or take your pants to a tailor.^{[6]
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- If you wish to look mature and impressionable, do not wear sweatpants or anything with an elastic waistband to school except during gym class.
2
Stock up on t-shirts. T-shirts come in almost any variety you can think of. You might prefer graphic tees with a cool image on them, or you may like the look of solid-colored tees in a v-neck. Try to choose a variety of styles so you can change up your look.^{[7]
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3
Get at least 2 button-down shirts. You don’t have to wear a button-down shirt to class every day, but rocking one every once in awhile shows that you care about your looks. Have at least 2 button-down shirts so you don’t show up to school in the same one every time you have to give a presentation. Your button-down shirts should drape comfortably around your torso, but they shouldn’t be too big or you’ll look sloppy.^{[8]
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4
Get a nice hoodie or jacket for cool days. Even the best outfit can look disheveled if you pair it with the worn-out coat you wore last year. Get a thick, comfortable hoodie or a zip-up jacket for a casual look that will still seem put together. If you’re going for a dressier look, opt for a peacoat or bomber jacket.^{[9]
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- A denim jacket or another statement jacket is best to wear with a plain t-shirt that has no pattern.
5
Have a nice pair of sneakers. Save your gym shoes for the basketball court and get a cool pair of sneakers to wear to class. Popular shoe brands include Nike, Adidas, New Balance, and Converse, but it’s more important that you find something you like and that you feel comfortable in than what’s on the logo.^{[10]
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Ask for clothes and gift cards for birthdays and holidays. You might not have a lot of spending money to go and create a new wardrobe right away, so just wear what you have and build up your new style a little at a time. Ask for clothes or gift cards to your favorite stores for your birthday or other special occasions. This will let your parents know you’re more interested in your appearance and they’ll be able to plan your gifts accordingly.^{[11]
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Method 3

Method 3 of 4:

Adding Accessories and Special Pieces

1
Wear a leather jacket if you’re going for a casual rocker vibe. A leather jacket is a timeless piece that instantly makes you look like you have a casually cool attitude. Look for a jacket that’s well-made, with sturdy stitching and heavy-duty leather. If you’re worried about the price tag, check local consignment stores or opt for a vegan leather.^{[12]
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2
Wear a pair of skinny jeans for a skater look. If you want to look like you could hit the skateboard at any moment, pair skinny jeans with a casual t-shirt and a pair of skate shoes or Converse. To really up the bad-boy look, stick to all-black.
3
Try a pair of corduroys in a bold color to upgrade your preppy style. If you love the clean look of preppy style, take your outfit to the next level with a pair of bold corduroys. Pair them with a slim-fitting button-down shirt or a sweater worn over a t-shirt.^{[13]
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Match your outfit to your sneakers for a street style look. Street style is all about the kicks. If you love the effortlessly cool hip hop vibe, find clothes that coordinate with your coolest pair of shoes.^{[14]
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Add your own touch with accessories. Once you narrow down your own style, start adding in accessories to make your look more unique. For instance, you might add buttons to your jean jacket to add a 90s rocker vibe to your streetwear look, or you might add a bold, funky watch in a bright color to an otherwise buttoned-down preppy look.^{[15]
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- Sticking to one bold accessory at a time will usually have the greatest impact.

Method 4

Method 4 of 4:

Looking Cool in a Uniform

1
Make sure your uniform fits you well. If you have to wear a uniform to school, it’s important that it fits you perfectly. Your pants should fit you comfortably in the waist and should just touch the tops of your shoes. Your shirt should fit close to your body, especially in the arms, shoulders, and chest.
2
Wear cool shoes. Even if your school has guidelines on the kinds of shoes you can wear, you should be able to find a cool pair that show your personality. For instance, many schools allow their students to wear athletic shoes with their uniforms, so you could wear your favorite sneakers. If your school requires you to wear dress shoes, find a dressy pair of lace-up shoes that still shows style, like a pair of low-cut oxfords. Replace your shoes when they start to fray or get holes.^{[16]
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Find unique accessories that fit the dress code. Your school likely allows you to wear at least a watch with your uniform, so look for one that really matches your personal style. A chunky plastic watch in a bright color might be perfect if you are into street style, while an inconspicuous leather watch with a gold face might be best if preppy is your thing.

Community Q&A

Question

How can I ask a girl out?

Community Answer

Just be completely straight forward and direct. Have an activity in mind. So say something like, "Do you want to go to the movies with me this weekend?" Girls appreciate it when a guy says what's on his mind rather than beating around the bush or acting uncertain.
Question

What goes well with slim-fit jeans?

Community Answer

A hoodie or a shirt that is not too tight, finished off with some cool sneakers.
Question

If I choose a style but others make fun of me, what should I do?

Amy Gremillion

Community Answer

Do your own thing without worrying what people have to say! It's important to find your own style in life. Remember that you won't be in school forever, so just ignore the people who make fun of you.