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Style Throwback: Soulja Boy's 'Pretty Boy Swag'

Where were you when this track dropped?

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This. Right here. Is my… woah, woah, woah, wait a minute. Not this hit song from 2010 making a spontaneous comeback thanks to TikTok. Most of us millennials remember exactly where we were in our lives when the song dropped (I was in high school), and how the song and video caused a ruckus on YouTube, so we may be rolling our eyes at Gen Z’ers just now making the discovery, but we have to remember that the fifteen-year-olds just now finding this song were the ripe old age of three when it came out, so we have to give them a pass.

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Whatever your age may be, it’s good to see “Pretty Boy Swag” back in heavy rotation, so we thought we would take it back to 2010 to do a little throwback on Soulja’s Pretty Boy era, but first, a little background on the current trend and song itself. Everybody. Pay. Attention.

What Is This Trend?

The “Pretty Boy Swag” trend is about revealing the personality traits of friends, family, and even yourself (both good and bad). Now this isn’t the first time that the song has become a major trend on the platform. Back in 2019, the single was used as the background tune for people to transform into their favorite pop culture heroes.

Pretty Boy Swag History

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Pretty Boy Swag was released in June 2010, charting at number 6 on the US Hot R&B/Hip-Hop Songs (Billboard), and number on the US Hot Rap Songs. The single instantly created a lot of chatter, and was both extremely catchy to us teens at the time, and quite annoying to our parents because of how much we played it over and over again.

Pretty Boy Swag Video One

Now here’s where we get into the style. Most people don’t remember this, but there were actually two videos released for “Pretty Boy Swag,” one official, one not. The official video was early 2010s rap style at its peak. Soulja rocking a white jacket paired with tan jeans and shades in the intro, then quickly transitioning to a black leather jacket that was worn over a black tank top and chains (you had to have the chains in 2010…you just had to).   

The video ladies wearing what we can only be described as 1930s British fashion meets the Avalon Nightclub in L.A.

Soulja meeting the girls waiting for him in his mansion wearing a plaid jacket and a massive “The World Is Yours Chain.” Can we get a price check on that chain somebody? What was worth then? What’s it worth now? Ben Baller can you help us out with this one?

Pretty Boy Swag Video Two

Now the unofficial video is the one that was for the culture. It was uploaded four months before the official video dropped (perhaps as a way to generate more conversation), and was a living breathing meme before memes were even a thing. There was also a dance that went with it (which you’ll see below), and only one look from each person in the crew, but boy was it memorable. All sorts of jackets, tees, and chains. Hats tipped at all kinds of angles. Loads of jewelry. The comments alone tell you everything you need to know.

“This video always gon be the better one”

“This video is a work of art honestly”

“Now this is the video i remember swag swag thank u based god”

And these are relatively recent comments left in the past year or two. 

The Performances

And let’s not forget the performances either. They were litty, and so was the style.

The all-white tank and joggers combo at his DC Six Flags Performance.

Him and Drake performing the song at Club Nokia in Los Angeles. Fun times.

Where were you when “Pretty Boy Swag” dropped? Will you be doing the challenge? Be sure to keep up with us for more style content and articles. 

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