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The difficulty in pinpointing Danny Brown's style and sound is exactly what makes him one of the most influential and lasting rap acts of the past 15 years. From his days slanging tapes in his hometown of Detroit to signing with Warp Records and traveling the world, the critically acclaimed rapper has achieved equilibrium with his mix of abrasiveness, humor, and soul.

Brown, being the unconventional rap star he is, also has to look the part. He has evolved past the toothy smile and wiry hair that defined him in his early days, using each record as a means to expand upon his lifelong fascination with fashion that began with mimicking his father's fondness for brands like Versace and Gucci.

During the rollout of his sixth album, Quaranta, all eyes are on Brown's outfits, which really emphasize the growth of his personal style ahead of his most introspective album yet.

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In one photo, the former Highsnobiety cover star can be seen sporting gender-neutral brand Done by Doug’s extremely distressed denim set and ultra-wide leg pants. Brown also loves a good statement shoe moment, pairing the ripped jeans with gold cowboy boots as an homage to his second home, Texas.

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On his recent co-headlining Scaring The Hoes tour with JPEGMAFIA, Brown wore more of Doug’s exaggerated pants, pairing them with New Rock shoes, a goth staple.

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And not being one to pass up the opportunity for a fun graphic print and pop culture references, Brown shows off a bootleg-style Denzel Washington shirt paired with a Björk tote bag and platform Dr. Martens – an outfit that can be found at most artsy college campuses and now on one of the most influential rappers of the past decade.

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Although Brown has always let his fashion freak flag fly, his Danny Brown Show podcast allowed him to show off his ‘fits even more. Now, what he calls “drip set” lives on the show’s TikTok account alongside viral clips of banter.

Brown also gives context to his weekly podcast outfits, like the full Ksubi set he purchased during a visit to Australia. 

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He’s even trudged into his office wearing Dallas-based brand Crimson Flow Studio’s ever-evolving Tar Clogs, which are designed to chip over time so that each pair is unique to the wearer.

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And although the MSCHF Big Red Boots were one of 2023’s biggest memes, Brown manages to style them successfully with baggy jeans and a Jaden Smith shirt (no clue how he found that). It’s hard to say Brown has an affinity for statement pieces when every element of the outfit looks like a statement.

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Brown’s fashion history goes way back, arguably before the likes of A$AP Rocky were seen as modern-day transgressive icons for male fashion. It’s become a sort of Blog Era legend that the reason 50 Cent refused to sign Brown was because he wore skinny jeans, for example, though Brown later corrected the record.

“I was wearing the skinny jeans and the thrift store clothes and sh*t like that,” he said in a later interview. “So [50 Cent] is like ‘No, you need to look non-approachable.’”

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Brown’s style evolution has always stayed true to his colorful personality. In 2013, stalwart menswear designer Mark McNairy recruited him for a wacky lookbook full of clashing patterns that mixed McNairy’s formal menswear ideology with Brown’s graphic tees and shorts.

Brown, whose juxtaposition of serious subject matter and eclectic production has made him one of rap’s most eccentric figures, was the best representation of McNairy’s foray into the weirder side of streetwear.

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After Brown walked in his Spring/Summer 2013 runway show, McNairy continued to work with hip-hop artists, enlisting Cam'ron and Travis Scott to model subsequent collections.

But Brown and McNairy's relationship is still going strong a decade later. In a recent 'fit check posted to his podcast’s TikTok, Brown showed off his full McNairy fit paired with the surgical boot-inspired MSCHF mules.

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And he’s never been afraid to stick out like a sore thumb. Case in point, Brown posed for a photo with an adidas-clad Kendrick Lamar and street style king A$AP Rocky wearing a Jeremy Scott tiger hoodie and a mismatched tropical print shirt. 

Brown always knew he was an outsider. It's exactly why he refused to bend to the rules of G-Unit, worked with independent record label Fools Gold, and showed off his chipped tooth smile for nearly a decade. No space was too sacred for a wacky fit, from the stage to the runway.

Much like his music, Brown's closet is a canvas for endless experimentation and he's continued to test the boundaries of his style since the world was first properly introduced to him over a decade ago.

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