Winter fashion in Hip-Hop has always been more than just about staying warm—it’s about flexing personal style, repping your neighborhood, and pushing boundaries. From the oversized puffer jackets and Timberlands that defined ‘90s streetwear, to the high-end designer collaborations that now turn heads, winter gear in Hip-Hop has been a constant evolution.
Whether it’s a rugged Carhartt work jacket or a North Face fleece, Hip-Hop culture has long blurred the lines between fashion and function. In this gallery, we’re taking it back to 1995, when Hip-Hop icons set the tone for the season’s hottest looks. Get ready to step into the past and celebrate the brands, the layers, and the bold statements that ruled the streets three decades ago.
VIBE highlights the winter gear your favorite rappers were rocking during the winter of 1995.
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Snoop Dogg
Image Credit: Ron Galella, Ltd./Ron Galella Collection via Getty Images Rapper Snoop Dogg attends Nineth Annual Soul Train Music Awards on March 13, 1995 at the Shrine Auditorium in Los Angeles, California.
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Salt N Pepa
Image Credit: Philippe AIMAR/AFP via Getty Images Vocalists Salt N Pepa pose with their Grammys for Best Rap Performance by a Group March 1, 1995 at the 37th Annual Grammy Awards in Los Angeles.
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RZA
Image Credit: David Corio/Redferns Photo of RZA; RZA of Wu Tang Clan/Gravediggaz in NYC 1995
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Dr. Dre, Suge Knight, Snoop Dogg
Image Credit: Nitro/Getty Images American rapper and producer Dr Dre (born Andre Young), record executive Suge Knight (born Marion Knight Jr), and rapper Snoop Dogg (born Calvin Broadus Jr) attend the premiere party for ‘Murder Was the Case’ (directed by Dre and Fab Five Freddy), New York, New York, circa 1995. The short film starred Snoop Doog and it’s soundtrack was released on Knight’s record label.
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Da Brat
Image Credit: Raymond Boyd/Getty Images Rapper Da Brat (Shawntae Harris) poses for photos on the red carpet during the 9th Annual Soul Train Music Awards at the Shrine Auditorium in Los Angeles, California on March 13, 1995.
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Will Smith
Image Credit: Margaret Norton/NBCU Photo Bank/NBCUniversal via Getty Images via Getty Images THE TONIGHT SHOW WITH JAY LENO — Episode 644 — Pictured: (l-r) Actor Will Smith during an interview with host Jay Leno on March 02, 1995 —
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Russell Simmons
Image Credit: Anthony Barboza/Getty Images Portrait of American businessman Russell Simmons (center fore), New York, New York, 1990s. With him are, from left, Boss, film producer Nelson George, Joseph Simmons (in sunglasses, also known as Run, and Russell’s younger brother) and Darryl McDaniels (left, also known as DMC), both members of pioneering rap group Run-DMC, and Tracey Waples.
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Kid of Kid ‘n Play
Image Credit: Rita Barros/Getty Images Portrait of American rapper Kid (of the group Kid ‘n Play, born Christopher Reid) (left) as he poses with an unidentified woman at the MK Club, New York, New York, 1990s.
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Redman
Image Credit: Raymond Boyd/Getty Images Rapper Redman poses for photos on the red carpet at the Shrine Auditorium in Los Angeles, California on March 13, 1995.
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Eric B., Jam Master Jay
Image Credit: Nitro/Getty Images Portrait of American rapper Eric B (born Louis Eric Barrier) (left), of the duo Eric B & Rakim, and Jam Master Jay (born Jason Mizell, 1965 – 2002), of the group Run DMC, as they pose together at an unspecified music industry event, New York, New York, circa 1995.
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Diddy, Aaliyah, The Notorious B.I.G.
Image Credit: Nitro/Getty Images Portrait of, from left, American rapper Sean Combs, singer & actress Aaliyah (born Aaliyah Haughton, 1979 – 2001), and rapper the Notorious BIG (born Christopher Wallace, 1972 – 1997) as they pose together during the ‘HOT Nite Jamaica’ event, sponsored by WQHT radio (‘HOT97’), Negril, Jamaica, December 1994.
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Beastie Boys
Image Credit: Gie Knaeps/Getty Images Adam Yauch (MCA), Mike Diamond (Mike D), Adam Horovitz (King Adrock), Beastie Boys, SAS Hotel, Brussels, Belgium, February 19, 1995.
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Mac Solaar
Image Credit: Alain BENAINOUS/Gamma-Rapho via Getty Images Mac Solaar, artist interpreter for male of the year and Enzo Enzo, artist interpreter for female of the year France on February 13, 1995.
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Naughty By Nature, Queen Latifah
Image Credit: Raymond Boyd/Getty Images Rapper Queen Latifah (Dana Elaine Owens) poses for photos with rapper Treach (Anthony Criss) (front), DJ Kay Gee (Keir Lamont Gist) and rapper Vin-Rock (Vincent Brown) of Naughty By Nature in the media room during the 9th Annual Soul Train Music Awards at the Shrine Auditorium in Los Angeles, California on March 13, 1995.
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B-Real, Treach, Everlast, Vin Rock, Sen Dog
Image Credit: Nitro/Getty Images Backstage portrait of, from left, American rappers B-Real (born Louis Freese), Treach (born Anthony Criss) (top), Everlast (Erik Schrody), Vin Rock, and Sen Dog (born Senen Reyes) during an event hosted by the Box tv network, Miami Beach, Florida, circa 1995. B-Real & Sen Dog are members of the group Cypress Hill, Treach and Vin Rock are members of Naughty by Nature, and Everlast performs with House of Pain.
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Shock G
Image Credit: © Tim Mosenfelder/CORBIS/Corbis via Getty Images Shock G of Digital Underground
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Lil Vicious
Image Credit: Raymond Boyd/Getty Images Rapper Li’l Vicious poses for photos at Fletcher’s One Stop in Chicago, Illinois in December 1994.
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Busta Rhymes
Image Credit: Steve Eichner/Getty Images Busta Rhymes at event, New York, 1990s.
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Queen Latifah
Image Credit: ABC Photo Archives/Disney General Entertainment Content via Getty Images 1995 AMERICAN MUSIC AWARDS – Gallery – Airdate: January 30, 1995.
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Shaggy
Image Credit: Erica Echenberg/Redferns/Getty Images Jamaican rapper Shaggy, circa 1995.
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Kool G Rap
Image Credit: Anthony Barboza / Contributor Low-angle portrait of American hiphop artist Kool G Rap (born Nathaniel Wilson) dressed in a denim jacket and a fishing hat, 1990s
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Coolio
Image Credit: Des Willie/Redferns Photo of COOLIO
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Ol’ Dirty Bastard
Image Credit: Al Pereira/Michael Ochs Archives/Getty Images Photo of Ol Dirty Bastard
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LL Cool J
Image Credit: Mitchell Gerber/Corbis/VCG via Getty Images Rapper LL Cool J rides a float with a number of young men in the Macy’s Thanksgiving Day Parade.
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Willie D of Geto Boys
Image Credit: Raymond Boyd/Getty Images Rapper Willie D. reads up on the latest hip-hop news after being interviewed at the Holiday Inn in Chicago, Illinois in March 1995.
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Ice-T
Image Credit: Margaret Norton/NBCU Photo Bank/NBCUniversal via Getty Images via Getty Images THE TONIGHT SHOW WITH JAY LENO — Episode 656 — Pictured: (l-r) Rapper Ice-T during an interview with host Jay Leno on March 20, 1995
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The Notorious B.I.G.
Image Credit: Ron Galella, Ltd./Ron Galella Collection via Getty Images Christopher “Notorious B.I.G.” Wallace in New York City, New York
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MC Hammer
Image Credit: Darlene Hammond/Getty Images Circa 1995, Headshot of American rap musician MC Hammer, 1990s.
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The Notorious B.I.G., Nate Dogg, Snoop Dogg, Diddy
Image Credit: Nitro/Getty Images Portrait of, from left, American rappers Notorious BIG (also known as Biggie Smalls, born Christopher Wallace, 1972 – 1997), Nate Dogg (born Nathaniel Hale, 1969 – 2011), Snoop Dogg (born Calvin Broadus Jr), and Sean Combs (also known as Puff Daddy and P Diddy) attend the premiere party for ‘Murder Was the Case’ (directed by Dr Dre and Fab Five Freddy), New York, New York, circa 1995. The film was produced by and starred Snoop Dogg.
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Dr. Dre
Image Credit: Vinnie Zuffante/Archive Photos/Getty Images Musician, producer and rapper Dr Dre (Andre Young) at the Billboard Music Awards, Los Angeles, California.
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Danny Boy O’Connor of House of Pain
Image Credit: Steve Eichner/Getty Images American Rap musician Danny Boy O’Connor (left), of the group House of Pain, posing with an unidentified man at the LifeBeat Board Aid 2 benefit at Big Bear Lake, California, March 15, 1995.
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Flava Flav
Image Credit: Danny Joint/PYMCA/Avalon/Getty Images Flavor Flav from Hip Hop group Public Enemy.
- Aaliyah
- Beastie Boys
- Busta Rhymes
- Coolio
- cypress hill
- Da Brat
- Danny Boy O'Connor
- Diddy
- Dr. Dre
- Eric B.
- favorite
- Fresh Kid Ice
- House of Pain
- Ice T
- Jam Master Jay
- Kid
- Kid N' Play
- Kool G Rap
- LL Cool J
- mc hammer
- MC Solaar
- Nate Dogg
- naughty by nature
- ol dirty bastard
- Queen Latifah
- Rappers
- Russell Simmons
- Rza
- Shaggy
- Shock G
- Snoop Dogg
- The Notorious B.I.G.
- uncle luke
- Will Smith
- winter
- Wore
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