How to Dress Cool in High School (for Guys)

Co-authored by Paul Julch, MA and Eric McClure

Last Updated: January 2, 2023

Do you wear the same t-shirts and baggy jeans every day? Do your parents still buy your clothing? Want to be stylish, but not sure how? Dress to impress with these simple tips.

Part 1

Part 1 of 3:

Before Your Shopping Trip

1
Decide what style you want to aim for. Consider the styles below:
- Casual: Casual style basically consists of simple jeans, t-shirts and sweaters. This is the safest and most common style among high school boys.
- Sporty: As the name suggests, this style is most favoured by members of school sports teams. The sporty style includes track pants, sneakers, sports team tops and varsity jackets.
- Preppy: The prep style is conservatively classy. This style involves lots of polo shirts, khakis and button-down shirts.
- Skater: The skater style is fun and functional. If you choose this style you'll be wearing lots of flat sneakers, skinny jeans, hats and accessories.
- Goth: The goth style is dark and brooding. The goth style has lots of black clothing, combat boots and trench coats.
- Emo: The emo style is philosophical and sensitive. You'll be wearing lots of skinny jeans, long bangs and band t-shirts. Be careful with this style, because if you don't do the style right then you might be labelled goth instead of emo.
- Hipster: The hipster style is vintage and anti-establishment. Expect to be wearing lots of skinny jeans, plaid shirts, big glasses and scarves as well as clothing that isn't "mainstream".
- Classy:The classy style is formal and out-standing. Lots of suits, nice pants, some scarves, good-looking shoes, belt, and maybe good watches (preferably a minimalist watch) that will show your esteem and how you aren't afraid of being different then the casual clothes, gangster type clothes, or "fashionable" clothes.
2
Research stores before you go shopping. This is important because some stores cater only to one of the above style groups. If you are worried about not being able to find what you're looking for, then try a mall since they have tons of stores in them.

Advertisement
3
Plan to take your friends along. You might think that neon yellow vest with purple stripes looks terrific on you, but they will probably have another opinion. However, if you still really like something after they give you the thumbs-down, buy it anyway as long as it isn't super expensive and you think that you will like it until you outgrow it.

Part 2

Part 2 of 3:

During Your Shopping Trip

1
No matter what style you are going for, select pants that fit you^{[1]
X
Research source}.
- Your jeans shouldn't be skin-tight, overly baggy, overly torn up or high-water.
- Get a pair of khakis or dress pants for formal occasions like dates, dances and job interviews. Make sure you get dressier pants in both lightweight and heavy fabric so you're ready for any weather.
- Jeans are appropriate for anyone, you can just choose a fit or colour that matches your chose style. For example, if you are goth or emo, pick out black jeans. Hipsters, pick out skinny fit jeans.
2
Stock up on short and long-sleeved t-shirts.
- Avoid shirts that are skin-tight or overly baggy.
- Keep in mind that stores size things differently, so always try on shirts before you buy them.
- Add a few button down or polo shirts to your standard t-shirt collection. Get these in both short and long-sleeved combinations. These types of shirts can be very versatile.
3
Keep the chill away with quality outerwear.
- Hoodies are a great, casual layer that give your outfits a casual and sporty look. You can also use a hoodie to dress down a blazer.
- For dressier occasions, get a few solid color sweaters. Avoid overly patterned sweaters and sweater vests, as these are generally though of as nerdy and unstylish.
- Blazers are great for dressing up a button-down shirt, or even jeans and a t-shirt. You might want to save this look for out of school events, however, as its a little formal for everyday wear.
- Invest in a quality leather, canvas or down jacket for chilly weather. Especially if you live in a cold region, you'll be wearing this every day so make sure it's flattering on you.
4
Get good shoes that you can dress up or down.
- Buy a good pair of sneakers to wear to school. Save your beat up tennis shoes for the gym! Converse, Vans or Superstars are your best bet for everyday school wear. They are always in fashion and will match most outfits. Choose a versatile colour such as black, grey, navy or maybe red or green if you wear those colours a lot.
- Invest in some quality leather shoes for dates, dances or dressy occasions.
- Get a pair of sturdy sandals - not flip flops - for hotter weather.
5
Beat the heat with stylish shorts.
- Cargo and jean shorts should be staple items in your summer wardrobe.
- Athletic shorts are appropriate on hot days as well, as long as they're not too short.
6
Accessorize. Accessories aren't just for girls.
- Get yourself a nice watch, pair of sunglasses and a quality belt.
- Grab a tie or two for formal occasions.
- The right hat can complete your look and cover up a bad hair day. Besides a standard baseball cap, consider purchasing a beret, newsboy cap or fedora to increase your classiness. Be careful about this though: only wear hats if you're sure you can pull it off.
- Depending on your comfort level, jewelry like necklaces, bracelets, rings and possibly even an/some earring(s) can add spice to an ordinary outfit. Just stick to one item at a time though, you don't want to overdo it.

Part 3

Part 3 of 3:

After Your Shopping Trip

1
Organize clothing purchases so they don't get hidden from view. If it's buried in the bottom of your closet, chances are you'll never wear it again.
2
Learn how to create stylish clothing combinations.^{[2]
X
Research source}
- Casual for Fall: Slip a hoodie over a T-shirt for a very casual and sporty look.
- Dressy for Fall: Wear a vest over a long sleeved button-down shirt with a tie. Add dress pants (with belt) and pair with leather shoes. If it's getting cold, top everything off with a leather jacket or blazer.
- Casual for Winter: Wear a short or long-sleeved t-shirt with jeans, sneakers and a hoodie. When you go outside, put on a down jacket, beanie and gloves and possibly a scarf.
- Dressy for Winter: Wear a blazer over a long sleeved button-down shirt with a tie. Add dress pants (with belt) and pair of leather shoes. For outside weather, stick to a non-leather coat.
- Casual for Spring: Wear a t-shirt with jeans and sneakers. Pair with a baseball cap or watch to add interest.
- Dressy for Spring: Wear a short or long-sleeved button-down shirt with a tie and khakis or dress pants. Add leather shoes.
- Casual for Summer: Wear a t-shirt and shorts with sneakers or sandals. Add a baseball cap and sunglasses to keep the sun out of your eyes.
- Dressy for Summer: Wear a short-sleeved button-down shirt with a tie and khakis or dress pants. Depending on the occasion, you may be able to swap sneakers for your leather shoes.

Community Q&A

Question

Are dress shirts too much for school?

Community Answer

Not at all. As long as it's not white, because that might be a bit much. Don't wear a tie with it, and maybe stick with casual pants.
Question

How do I create stylish clothing combinations?

Community Answer

Don't wear what everyone else is wearing. Try to stay unique, but not like you are trying to hard. Make sure colors complement each other, like khaki color pants, and a navy shirt. Different shades of dark blue for example, are a no go, as well as 2 bright colors like red and yellow.
Question

What do I do wear with white shoes when trying to dress cool?

Community Answer

Black joggers or jeans. Throw in a sweater/hoodie and you'll look casual and laid back.

Warnings

Don't wear the same "great" outfit over and over.

⧼thumbs_response⧽
Helpful 10 Not Helpful 0
Don't wear sweater vests and shorts.

⧼thumbs_response⧽
Helpful 7 Not Helpful 0
Don't buy uncomfortable clothing. If you can't move your arms or legs properly, you're going to look silly even if you're wearing super stylish clothes.

⧼thumbs_response⧽
Helpful 6 Not Helpful 0
Don't wear pants that reveal your underwear. No one wants to see that!

⧼thumbs_response⧽
Helpful 9 Not Helpful 1
Don't wear the same clothing combination every day. It's tempting to fall into a rut, but try to shake things up. Wear a vest with your favorite shirt, add a belt to your shorts or substitute a sweater for your usual sweatshirt.

⧼thumbs_response⧽
Helpful 5 Not Helpful 0
Don't wear socks and sandals. This is never a flattering combination.

⧼thumbs_response⧽
Helpful 6 Not Helpful 1
Don't let your parents buy your clothes. They may be well-meaning, but it would be a gigantic mistake to take their fashion advice.

⧼thumbs_response⧽
Helpful 6 Not Helpful 2