Is it just me or does nobody talk about how men’s fashion has taken a crazy turn, evolving into something nobody saw coming. I mean, I wouldn’t say I’m a fan of the modern day Yeezy wearing hoodie dripping, bucket hat wearing consumer. However i can’t deny the long road it has gone down exploring so many unique style statements, inspirations and looks. Let’s take a trip down the memory lane of some of the most notable teenage boy fashion looks from the past decades.


In the 1950’s, teenage boy’s fashion was for the first time, different from their father’s. The iconic “Greaser”, “Teddy Boy”, “Jock” and “Nerd” were all the different subcultures within current fashion choices. The Teddy Boys were the British boys who started the teenagers as a consumer group movement.

They choose to wear the Edwardian Suits of their father’s with the pants slimmer and shorter, often showing off vivid and socially unacceptable socks giving them more of a ‘Square’ appeal. The second picture, seniors laughing at themselves in their newly minted yearbook, showed that during the 50’s, men’s clothing was crisp and well kept, even the Greaser’s ringer-shirt was purposely tucked into their jeans. Wrinkles and sloppiness was not acceptable.

Fashion standards were often set by celebrities. Marlon Brando and Elvis Presley were responsible for major changes in the way the teenage males dressed. Both gave the rebel or the Greaser major fashion lessons. Marlon Brando is shown wearing a ringer T-shirt, black leather biker jacket, 501 Levi Jeans and a stingy brim hat. He is basically wearing the iconic“Greaser” look. Elvis, on the other hand,presented a more mainstream look, still pushing social boundaries with his style of music and moves. He is often credited more for this and his hair styles than his  

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 “A white sport coat and a pink carnation”, and when it came it Prom, yes, a white sport coat with a pocket square handkerchief, black bow-tie, black slack or tuxedo pants and a white shirt was the number one choice for young men. The current fashion of a black shirt was unheard of; however “pops” of color could be seen in shirts from the rebellious young gentlemen wearing their “Sunday Best Suits”.

Also, please note, the young men DID NOT match their ties to their date’s dresses. Speaking of dates, it was customary to give your date a corsage of flowers, usually a wrist corsage, which is easier to wear for the young lady, but occasionally she would be given a shoulder corsage, and you did not have to worry about it, because your mom took care of it for you.

You in return were sometimes given a boutonniere to wear on the lapel of your jacket. Also frequently worn were both dark suits and lighter beige suits, sometimes worn with bow ties, other times worn with thin ties. Both the white sport coat and the regular suit options were worn with well cared for shoes with a shine, or if you had it, blue suede shoes (once again imitating a favored pop icon). Prom was the Social Event of High School and you wore the best you could afford. Prom was often the first time Dad would let you solo at night with the “good” family car and curfews were generally lifted until 11pm. There was no such thing as an organized After Prom celebration. Oh the good ol’days!

Often being arrested for drag racing, the greaser’s in the pictures are wearing normal everyday clothing for the young rebellious group of men. Notice that the jeans and the chinos are very baggy in fit, the shirts are all tucked in and undershirts are worn under the button up shirts. The greaser jackets were never just dead on matches to each other, but rather each male had his own style and his jacket reflected that. Other types of jackets and coats were worn as well such as – Work jackets in black, blue and khaki.Trench coats were seen in both black and brown. Levi denim jackets were also worn as well as windbreakers. John Travolta wears a blue windbreaker in the opening sequence of “Grease!” as a homage to James Dean.


The 70’s and 80’s were a big switch! Transitioning into a more colorful world- more prints and more color dominated the media eventually with the popularization of color TV. Technicolor in the media inspired some crazy funky looks for both men and women.Casual fashion in the ’80s saw your average dad jeans in full force, often with a matching denim jacket. T-shirts and loose shirts were also popular during the time while bomber jackets, leather jackets, windbreakers, and sweaters acted as the outerwear of choice. When it came to footwear, white sneakers were the ultimate casual shoe that’s perfect for a range of looks.

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Hip Hop

Hip-hop was another popular fashion subculture  in the ’80s. Inspired and influenced by music stars and rappers, such as the members of Run-D.M.C, Beastie Boys, and N.W.A, the style was well known for its oversized silhouettes and baggy pants. Along with baggy clothes, hip-hop fashion also featured sportswear details, like sneakers and athletic caps, and statement accessories, like chunky gold chains. Interestingly this style is coming in fashion in 2020 in full force!

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80s Preppy Fashion

Preppy fashion also played an essential role in the ’80s. Unlike hip-hop trends, which typically featured dark colors, preppy outfits boasted bright hues, including shades of pink, yellow, and blue. Key items for preppy fashion included sweaters, which gents would often wear around their shoulders, as well as slacks and polo shirts. Interestingly preppy outfits were often associated with wealth and privilege. Remember Carlton from Fresh Prince of bel Air in contrast to will Smith’s more Hip Hop style.


Nothing beats the 90’s with its Boyish, grunge look!. Celebrities like Johnny Depp, Brad Pitt and James Franco were style icons of the 90’s. Aviator sunglasses, baggy sweaters and man… a whole lot of denim!  It was all about looking like a bad boy, I’d say it was kind of bringing back the 60’s greaser look. Cargo pants had their moment of cool in the ’90s. With so many pockets you could carry your wallet, Gameboy and even a pager, these pants were practical and in fashion. While originally worn oversized and baggy, today’s cargo pants tend to look best with a slim or tapered fit.

When it came to jeans in the ’90s, the rule was; the baggier, the better. These supersized pants were a must-have of the day and quintessential to any streetwear look. They were also worn low on the hips and often accompanied by a chain with a Velcro wallet attached to the end. This went along with the 90’s Hip Hop fashion.

Remember Will Smith from The Fresh Prince of Bel’Air, His Windbreakers were massive in the ’90s and have made an epic return in recent seasons. These lightweight, wind-resistant jackets are perfect for projecting a retro sporty style, especially when worn in bold block colors, just like it was worn in the 80’s.  It’s evident that a lot of the throwback styles keep returning to style, making quick comebacks every now and then

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2020’s Hot boy look is not so hot because it’s simply just another throwback to all the other styles we’ve uncovered, instead turning it out to be rather obnoxious in its desperation to look like just another Travis Scott type.

Sure men are a lot more confident now than they were in the 90’s in terms of embracing a type of femininity through fashion, however the other subcultures of young boys drown themselves in designer brands and labels – the end result is a carbon copy of just another guy on social media- it’s hard to tell who’s who when everyones wearing the same thing. The evolution kind of just stops there, and sadly until we get rid of influencer fashion we will not grow as stylish individuals.

Media in 2020 runs the show, both through social media and other online platforms making a big deal out of influencer fashion- that’s really what’s dominating the fashion market. Ask yourself men, do you really see growth in Men’s Fashion in 2020?

fashion evolution of the teenage boy