How to Dress Cool in High School (for Guys)

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 of 3: Before Your Shopping Trip

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   Decide what style you want to aim for. Consider the styles below:
   

   • 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,good watches(preferred Rolex)and will show your esteem and how you aren't afraid of being different then the casual clothes,gangster type clothes,or "fashionable"clothes.
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   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.
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   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 anyways as long as it isn't super expensive and you think that you will like it until you outgrow it.

Part 2 of 3: During Your Shopping Trip

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   No matter what style you are going for, select pants that fit you^[1].
   

   • 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.
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   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.
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   Keep the chill away with quality outerwear.
   

   • Hoodies and sweatshirts are a great, casual way to keep warm.
   • For dressier occasions, get a few solid color sweaters. Avoid overly patterned sweaters and sweater vests unless you are confident enough to pull them off.
   • Vests can add interest to any shirt and will boost your style level instantly. So get a bunch of different types of vests so that you can accessorize any outfit with a vest.
   • Blazers are great for dressing up a button-down shirt, or even jeans and a t-shirt.
   • 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.
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   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!
   • Invest in some quality leather shoes for dates, dances or dressy occasions.
   • Get a pair of sturdy sandals- not flip flops-for hotter weather.
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   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.
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   Accessorize. Accessories aren't just for girls.^[2]
   

   • 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.
   • Depending on your comfort level, jewelry like necklaces, bracelets, rings and possibly even an/some earring(s) can add spice to an ordinary outfit.

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   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.
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   Learn how to create stylish clothing combinations.^[3]
   

   • Casual for Fall: Wear a short or long-sleeved t-shirt with jeans and sneakers. Add a baseball cap and watch, plus a hoodie if it's getting cold.
   • Dressy for Fall: Wear a vest over a long sleeved button-down shirt with a tie. Add khakis or dress pants (with belt) and pair with leather shoes. If it's getting cold, top everything off with a leather jacket or blazer. A fedora or newsboy cap makes a nice finishing touch!
   • 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 vest or blazer over a long sleeved button-down shirt with a tie.^[4] Add khakis or dress pants (with belt) and pair with leather shoes. For outside weather, stick to a leather or canvass jacket plus a fedora or newsboy cap.
   • 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 and a vest.
   • 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 might be able to substitute sandals for the usual leather shoes.

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Midou Osbourne