59 Cool Outfits For Teenage Guys (2023 Boy's Fashion Trends) (2023)

Men’s fashion is constantly evolving, and many teenage guys may be wondering what to wear. These days, teen boys have more clothes and styles to choose from than ever before. With several different ways to mix and match pieces, it can be a challenge knowing how to dress to create a fashionable outfit. Some guys prefer wearing jeans, a t-shirt and trainers while others will want to elevate their look with chino pants, a button-down shirt, and sneakers. Whether you want to look stylish for a date or just need comfortable and cool outfits to wear to high school, it’s important to invest in wardrobe staples that can be styled to suit any occasion. To inspire you with ideas, we’ve compiled a guide to the best outfits for teenage guys. From trendy styles to casual attire, explore the latest fashion trends for teen boys to find cool styles, outfit ideas, and clothing you’ll love.

Cool Outfits For Teenage Guys

T-Shirts

Simple and casual, guys can’t go wrong with quality t-shirts. Whether you’re creating a casual outfit to hang out with friends or need layers under your flannel in the fall, there are many different t-shirt styles to add to your wardrobe.

While crew neck shirts are versatile and easy to wear, you’ll need to focus on fit. The chest and arms should be snug but not tight, and air should be able to circulate in the torso without being visibly loose.

There’s room for more flow depending on the t-shirt’s cut. Loose scoop necks and stylish v-necks can look effortlessly cool. Meanwhile, slightly relaxed linen henley shirts offer a mature and fashionable look. Baggy shirts are back from the 90s, but should be styled in a fashion-forward way.

When styling outfits, you’ll want to wear a black or white cotton t-shirt with jeans and white sneakers. Dress up the look by cuffing your jeans and featuring a bomber or denim jacket. You can also pull off a cool casual look by pairing navy or tan chinos with an oversized shirt and loafers.

With limitless shirts for teenage guys to choose from, you’ll want to experiment with different outfit ideas to find the right style.

Jeans

You can create thousands of looks for every season with just one pair of jeans. Since they come in several cuts, washes, and designs, jeans are essential to every teen guy’s wardrobe regardless of personal style. Normal and relaxed cut jeans are the most common options, but straight leg and skinny jeans make casual outfits look stylish without trying too hard.

Slim-fit jeans are similar to skinny jeans, but with a more relaxed calf. They’re effective as an understated, timeless look, or for guys who are bigger in the hip and waist area because the slim cut evens out the silhouette. These types of jeans also go well with most footwear, including leather dress shoes, Converse sneakers, Vans slip-ons, and leather sneakers.

Neutral and versatile, guys can wear black jeans with casual, smart-casual, and urban chic outfits. Blue jeans are classic wardrobe staples and can be styled to stand out or blend in with your outfit.

Distressed denim and ripped jeans are two expressive options with a cool streetwear feel. School-appropriate and easier to wear than skinny cuts, every teenage boy should own a pair of distressed jeans.

For an autumn look that’s relaxed but slick, you can pair slim dark blue jeans with black sneakers, a dark loosely hanging infinity scarf, and a textured tan sweater with the sleeves rolled up just below your elbows. For a cool downtown take on this look, swap out the sweater for a t-shirt and bomber sweater, and top it off with a beanie.

Pair slim jeans with a neutral shirt, then experiment with fun accessories like a large watch or colorful sneakers. Roll up a short sleeves shirt for a vintage James Dean look.

Chinos

A lot of teen guys don’t realize that you can wear chinos casually. Wearing these pants with a laid-back outfit elevates the whole look without making it formal. Since chinos complement many styles including skater, preppy, and even dapper, they’re a true fashion fundamental.

Their sturdy build makes chinos perfect for cuffing. This is a bolder, more fashion-conscious look. Shorter guys might be insecure about looking smaller in cuffed pants, but slight, one-inch cuffs on tapered chinos look stylish without visually diminishing any height.

Cuffed chinos style well with a layered look. Wear them with a sweater, jean jacket, and low-profile white sneakers. Go for no-show socks on warmer days, and visible solid or striped socks to match your sweater on cooler days.

For a timeless smart casual look, wear chinos with a button-down shirt and leather sneakers or dress shoes. For more casual occasions, you can untuck completely, half-tuck, or do a loose front tuck for a laid-back summer vibe topped off with your favorite sunglasses.

Shorts

Shorts are necessary to keep stylish and cool during spring and summer. You can even use short versions of specific pant styles, like chino shorts and ripped jean shorts, to make your favorite fall outfits spring-appropriate.

Make sure each pair of shorts stop right above the knee cap so it looks casual but not sloppy. For the beach, pool, and just lounging around, swim trunks and athletic shorts are comfortable options that can also be fashionable.

There’s more freedom during spring and summer to try fun prints and loud colors so try your favorite color in neon at your next pool party. There are even shorts made of dress pant materials for a hip, unique take on the gentleman look.

For a fashion-forward approach, ripped denim shorts look great with a simple shirt, sneakers, and a flight jacket or fitted hoodie. Meanwhile, chino shorts feature clean lines that visually match a short-sleeve dress shirt or a fitted t-shirt. Pair this outfit with clean white sneakers or boat shoes, and bring the whole look together with a sports watch.

Button-Down Shirt

Whether you’re going on a first date or just dressing up a casual outfit, button-down shirts are easy to style and always fashionable. These shirts range widely from formal to very relaxed, so teenage guys need to have options.

Wear spread collar shirts with the top unbuttoned, and wear buttoned collar shirts with ties or layers. Utility shirts and shirt jackets are similar to each other, both featuring several lines and pockets, but shirt jackets are slightly thinner and meant to be worn as a top layer.

When styling a spread collar button-down, sport dark slim jeans and leather sneakers for a casual but tailored style. While buttoned collared shirts are meant for upscale occasions, you can pair these tops with a relaxed fit sweater, chinos, and white sneakers for a sleek and casual back-to-school look.

Flannel Shirt

Flannel shirts are a fall wardrobe staple for stylish teenage guys. Since there are so many ways you can wear a flannel, it’s your best bet when you want to look good on days that are too warm for a jacket but too cool for just a shirt.

Typically, you’ll save the full-tuck for camping or hiking. If you’re going for a full-on outdoorsy look, try pairing your full-tuck flannel shirt with an outer layer, like an open puffer jacket, and top it off with a beanie. Wear your flannel completely unbuttoned over a v-neck t-shirt with dark jeans and chukka boots for an effortlessly cool look.

You can even complement different streetwear looks with a flannel shirt. For an edgier vibe, wear a long flannel shirt over a t-shirt, but under a jean jacket. Finish this look with fitted, even skinny, ripped jeans and Chelsea boots. For a cleaner urban look, dress up a perfectly fitted flannel, buttoned to the top, with slim dark jeans and chukka boots.

Hoodie

With the right hoodie, you can kick up your outfit with an urban athletic flare or a masculine woodsy feel. Whether you’re opting for a close-to-body sports fabric, a heavy plaid with shearling, or anything in between, add a stylish hoodie to your rotation for shape and variation.

Classic hoodies can be worn loosely for a cozy look or fitted for a streamlined city chic approach, perfect for layering. A classic-fit knitted hoodie with high-density yarn can be paired with distressed skinny jeans and sneakers for a scenester style, or with chinos and boat shoes for a preppy look. Baja hoodies are boho-chic while designer hoodies must be worn with minimalist outfits.

When it comes to styling, a fitted hoodie shirt constructed with thin fabric paired with skinny jeans and sneakers is a confident style that girls love. During cold seasons, style a flannel shearling hoodie with dark slim jeans, boots of your choice, and either a flat brim cap or beanie depending on your personal tastes.

With so many different styles in a range of fabrics and patterns, a hoodie can be styled as outerwear, a secondary layer, or the primary top.

Denim Jacket

Denim jackets are an easy way to add architecture and dimension to an outfit. Even a rolled-out-of-bed sweatpant look can be saved with a stylish jean jacket, which is why every teenage guy needs at least one of these in their closet.

There are three main denim jacket styles. The classic denim jacket always looks great in blue and looks more modern and chic in black. The hooded denim jacket serves up a multi-layer look even when you’re not layering much. Colored denim jackets are fun and loud, but must be matched accordingly since they don’t go with everything like the classic blue and black do.

A blue denim jacket with a shearling interior and lapel goes handsomely with chinos, a utility shirt, and aviator sunglasses. For a fashion-forward look that doesn’t overdo it, wear an oversized denim jacket with a minimalist monochrome shirt and pants. Guys can accessorize the outfit with a bright statement hat, like a red flat brim cap.

Classic denim jackets are exceedingly easy to style and can elevate any look. Explore different fits and colors to suit your desired aesthetic for different occasions.

Jackets

Jackets are about more than just keeping you warm. A jacket is a type of outwear that can make or break your look. Functional and stylish, you’ll want to find a jacket style that will take a simple outfit up a notch.

For a casual look, invest in fitted puffer jackets, parkas, and athletic jackets to add weight while emphasizing your body shape. Trench coats and pea coats are classier options that can still be dressed down if you pair them with clean-lined slim jeans.

Leather jackets are the best of both worlds when it comes to being upscale and being laid-back cool. Most teen guys may not go for sport coats, but you can really make a sport coat cool if you pair it with a graphic t-shirt and roll up the sleeves.

There’s always a place for bomber jackets, which come in several styles and fits. A red or blue bomber with lined lapels is both vintage and enduring, large aviator-style bombers with patches are a fashionable statement look, and fitted bombers in a thin fabric boast a clean and athletic silhouette.

Wear a monochrome earth-tone t-shirt and jeans combo with chukkas, a bright beanie, and a fur-lined parka for a simple casual outfit that still has some understated swag. A slim puffer jacket paired with dark chinos and leather sneakers (dressy or casual) offers the perfect combination of practical sporty and high-end chic. Always opt for a pea coat or trench coat if you’re going to a formal event like prom or a wedding.

From winter formals to back-to-school, a lot happens during the cooler seasons, so it’s important to have several jackets in several styles.

Sweatshirt

Because of their simple build and uncomplicated lines, you can have a lot of fun with different kinds of sweatshirts. From colors to patterns and fitted to baggy, sweatshirts are easy to wear because you can always take them off.

A sweatshirt is more casual than a sweater and is often associated with a sporty style. In recent years, every brand name designer makes a few minimalist sweatshirts. Crew neck sweaters are the most common, v-necks can show off a collar, and scoop necks go perfectly with an oversized, relaxed look.

For a playful but fashionable aesthetic, wear an oversized bright sweatshirt as a color block with dark pants or faded jeans and leather sneakers. Create a cool collegiate look by pair an athletic sweatshirt with chinos, and white sneakers. The relaxed look of the sweatshirt makes this otherwise conservative style more personable.

Shoes

The shoes you pair an outfit with can mean the difference between smart casual and just casual, or trendy vs classic. When it comes to fundamentals, every teenage guy needs low-profile leather sneakers, trainers, white sneakers, boots, and dress shoes.

Low-profile leather sneakers or dressy sneakers are a mature but still youthful look, and Common Grounds are the reigning gold standard. Jodhpur and Chelsea boots feature a clean, iconic silhouette that go well with jeans or dress pants. Chukkas are a more casual boot, especially if they have a crepe sole.

If you want to go for a hip-hop vibe, high-top sneakers are fun footwear with bulk that beautifully contrast skinny jeans. If you want to go for an uptown Ivy League vibe, boat shoes come in a lot of fun colors and materials like canvas and leather.

When it comes to styling, matching your shoes with your outfit is the classic route, and contrasting is the modern and fashion-forward path. For example, you can always pair a dressier outfit with leather sneakers over dress shoes, as long as you aren’t wearing a tie. This look is the epitome of smart casual.

Similarly, pairing dress shoes with a t-shirt and jeans makes it more curated looking. Since layered outfits are reminiscent of the outdoors, boots and sneakers go best in this situation.

Try wearing boots, especially chukkas, with black jeans and a t-shirt for a sleek style. Top it off with a bomber jacket for a hip relaxed look, or a sport coat for something a little more formal.

Watch

As a teen guy, nothing makes your outfit look more put-together than wearing a watch. While sport watches are the most versatile, there are many styles to consider when shopping. The type of watch you get will be determined by your taste, aesthetic, and budget.

When it comes to investing in a timepiece, getting a stainless steel luxury sport watch is better than buying multiple cheaper accessories. Designer watches are always in style and keep their value. If you want to mix and max to pair with different looks, there are two main rules to keep in mind.

First, men should pair a high-end sport or dress watch with smart casual or business professional outfits. Second, combine your favorite timepiece with casual looks. Yes, even upscale leather watches can go with laid-back looks.

Colorful watches look great with monochrome outfits. If you’re wearing a leather strap, coordinate it with your belt and shoes for cohesiveness. The rugged aesthetic of field watches go well with layered looks and athletic wear.

There’s no wrong way to love a watch. Except for the aforementioned fundamental rules, you should have fun experimenting with different timepieces.

Summer Outfits

Go the loose and breezy route during the dog days of summer. It’s the one time of the year that you can sport beachwear even if you aren’t near an ocean. While loose clothes and lighter colors are more comfortable in hot temperatures, they also just pop better visually when the days are longer and you’re spending more time outdoors.

Stick to light materials like cotton and bright colors like reds and sky blue. If you prefer neutrals, gray and white are perfect for the season too. Enjoy all of your favorite short-sleeve t-shirts and accessorize them with trendy sunglasses, watches, and hats.

White denim and light-colored chinos pair well with any t-shirt, as do white sneakers and any style slip-on. Summer is also a good time to bust out loud colors like neons and pinks, if that’s your style.

Fall Outfits

Teen guys looking for fall outfits to wear to high school or college will want to invest in high-quality pieces. During back-to-school season, your fall wardrobe should be full of cool and traditionally proper styles with a variety of fits, colors, and designs. The most popular outfit ideas in the fall will take advantage of layering.

Cable-knit may look too preppy with chinos, but if you pair it with dark skinny pants, a ripped jean jacket and beanie, it fully transforms into an artsy style. For a simple and casual style, you can wear blue slim-fit jeans with a sweatshirt, navy chinos with a button-up shirt, or black jeans with a hoodie and white sneakers.

Layering not only allows you to get creative with your pairings (upscale with casual, simple with complex), but it allows you to accommodate the unpredictable autumn weather. Shed a layer if it gets too warm, and put it back on when it gets cold.

Oranges, tans, and browns match the changing fall leaves, but earth-toned pops of color add dimension too. Forest green sneakers or a brick red knitted scarf are great examples of this.

Winter Outfits

Your winter style will need to be trendy, comfortable and warm, resulting in outfits that are layered with complementary pieces. Teenage guys will want to invest in wardrobe essentials made with cozy fabrics and dark colors that can be combined to create a range of cool looks. The holiday season also means that winter whites and shiny accessories also have a place in your closet.

For winter outfits, black will always work and can be dressed up or down to suit the occasion and desired aesthetic. Whether you’re going to a winter formal or taking a girl out on a date, you can wear black leather jackets, jeans, and trench coats for a fresh look. A dark monochrome style is usually a statement, but these ensembles are perfectly conventional and fashionable during the cold months.

Holidays like Christmas and New Year’s Eve mean that you can also incorporate gold, silver, and whites into outfits. The best way to do this without going overboard is through accent colors such as the buttons on your shirt, lines on your shoes, or designs on your sweater.

Spring Outfits

Spring fashion and clothing should be about welcoming the ability to enjoy the outdoors. The main difference between summer and spring styles is the dominance of pastels and lighter shades over brighter shades. You might wear a bright electric green t-shirt in summer, but choose a lighter Easter green in the spring.

Like in summer, lightweight fabrics are a must, but there’s still room for moderate layering. The open flannel over a t-shirt paired with cuffed pants, socks, and sneakers that you wore in fall could be remixed into an open plaid shirt jacket with no-show ankle socks. For teenage guys who aren’t excited about pastels, matching grays with whites is a neutral option that’s still spring-appropriate.

Slip-on shoes and white sneakers are staples in warm weather, but especially in spring. If you’re a fan of color, this is the best season to try out bright leather dress sneakers with white soles or even floral print collared shirts.

Teen Boy Fashion Trends

• The best outfits are well-fitted styles that combine timeless classics with fun trends and feature subtle contrasts throughout.
• For a casual look, always have at least one item of clothing that’s well-fitted so your outfit doesn’t look sloppy. You can pair a clean-lined shirt with relaxed-fit jeans or an oversized shirt with shorts that properly stop right before the knee.
• Create a smart casual style by figuring out where comfort is most important to you. If you’re walking around a lot, wear sneakers with a smart outfit. If you’d rather not wear a collar, then wear a t-shirt with a sport coat and dress shoes. Teen boys will want to combine comfortable pieces to achieve the perfect casual outfit.
• From trainers to white leather sneakers, your footwear will make or break the outfit. A neutral t-shirt and jeans can look completely different when paired with dress shoes, white leather sneakers, or black tennis shoes.
• Outerwear and accessories add personality to your aesthetic. You can liberally feature an unconventional watch, scarf, or hat for a fun and unique look. Accessories are a great way to experiment and create your own style with flair.