A Day With Diplo, His Boxers, and That “Dad After Dark” Look

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Diplo is the most underrated charmer on the red carpet. He has dimples! He has quippy one-liners! And perhaps most importantly of all, he has the style to match. Need proof? Ahead of this week’s Grammy Awards, the Vogue team got to spend an intimate 24 hours getting ready with the DJ as he jetted from Los Angeles to Las Vegas and back again. In this jam-packed day, we see Diplo in a number of states: getting dressed in his underwear, doing downward-facing dog at yoga, feeding his chickens, mixing in his recording studio with artist Tove Lo, hopping on his private plane—you get the picture.

Throughout the pre-Grammys experience, we learned a lot about Diplo’s style too, which he refers to as “dad after dark.” For one, he wears briefs, not boxers, that are monogrammed with his name on the elastic band. He also spills that he once went watch shopping with Post Malone, who convinced him to splurge on an $80,000 watch (which he wore once). Picking ensembles for the awards show and a party with J Balvin, there is a cornucopia of options on his clothing rack, including a lime green bomber jacket from Prada and a retro Missoni striped suit. Perhaps Diplo himself summarizes his fashion taste best: “Just like my brand of music, it [my style] is kind of random; it does whatever.” We’ll take it.

Here, see what it’s like spending a day with an on-the-move Diplo.

Director: Rony Alwin
DP: Maritza Garcia
Sound: Rich Roy

See All of the Celebrity Looks From the Grammys 2019 Red Carpet:

Grammy Awards 2019: See Every Look Live From the Red Carpet

Cardi B in archive Mugler and Gismondi1754 jewelry
Cardi B in archive Mugler and Gismondi1754 jewelry
Photo: Getty Images
Katy Perry in Balmain with Djula jewelry
Katy Perry in Balmain with Djula jewelry
Photo: Getty Images
Jennifer Lopez in Ralph & Russo and a Judith Leiber Couture bag
Jennifer Lopez in Ralph & Russo and a Judith Leiber Couture bag
Photo: Getty Images
Travis Scott in Saint Laurent and Kylie Jenner in Balmain, Jimmy Choo shoes, and Lorraine Schwartz jewelry
Travis Scott in Saint Laurent and Kylie Jenner in Balmain, Jimmy Choo shoes, and Lorraine Schwartz jewelry
Photo: Getty Images
Lady Gaga in Celine by Hedi Slimane, Jimmy Choo shoes, and Tiffany & Co. jewelry
Lady Gaga in Celine by Hedi Slimane, Jimmy Choo shoes, and Tiffany & Co. jewelry
Photo: Getty Images
Post Malone
Post Malone
Photo: Getty Images
Tracee Ellis Ross
Tracee Ellis Ross
Photo: Getty Images
Dua Lipa in Bulgari jewelry
Dua Lipa in Bulgari jewelry
Photo: Getty Images
Anna Kendrick in Nikos Koulis jewelry
Anna Kendrick in Nikos Koulis jewelry
Photo: Getty Images
Kacey Musgraves in Valentino
Kacey Musgraves in Valentino
Photo: Getty Images
Janelle Monáe in Tiffany & Co jewelry
Janelle Monáe in Tiffany & Co jewelry
Photo: Getty Images
Hennessy Carolina
Hennessy Carolina
Photo: Getty Images
Young Thug
Young Thug
Photo: Getty Images
Zedd
Zedd
Photo: Getty Images
Patrick Stump, Andy Hurley, Pete Wentz in Saint Laurent blazer, Givenchy shirt, Burberry pants and Magnanni shoes, and Joe Trohman of Fall Out Boy
Patrick Stump, Andy Hurley, Pete Wentz in Saint Laurent blazer, Givenchy shirt, Burberry pants and Magnanni shoes, and Joe Trohman of Fall Out Boy
David Crotty
BTS
BTS
Photo: Getty Images
Pusha T in Thom Browne
Pusha T in Thom Browne
Photo: Getty Images
J Balvin
J Balvin
Photo: Getty Images
Ella Mai in Tiffany & Co jewelry
Ella Mai in Tiffany & Co jewelry
Photo: Getty Images
Kelsea Ballerini in Jenny Packham and Eva Fehren jewelry
Kelsea Ballerini in Jenny Packham and Eva Fehren jewelry
Photo: Getty Images
Dolly Parton
Dolly Parton
Photo: Getty Images
Halle Bailey and Chloe Bailey
Halle Bailey and Chloe Bailey
Photo: Getty Images
Miley Cyrus in Mugler and Loree Rodkin jewelry
Miley Cyrus in Mugler and Loree Rodkin jewelry
Photo: Getty Images
Heide Klum in Jimmy Choo shoes with a Judith Leiber Couture bag
Heide Klum in Jimmy Choo shoes with a Judith Leiber Couture bag
Photo: Getty Images
Bebe Rexha in Monsoori and Hearts On Fire jewelry and Amwaj earrings
Bebe Rexha in Monsoori and Hearts On Fire jewelry and Amwaj earrings
Photo: Getty Images
Tierra Whack
Tierra Whack
Photo: Getty Images
Leon Bridges in Bode
Leon Bridges in Bode
Photo: Getty Images
Meghan Trainor in Forevermark Diamonds jewelry
Meghan Trainor in Forevermark Diamonds jewelry
Photo: Getty Images
Miguel
Miguel
Photo: Getty Images
Alicia Keys in Aquazzura and Bulgari jewelry
Alicia Keys in Aquazzura and Bulgari jewelry
Photo: Getty Images
Shawn Mendes
Shawn Mendes
Photo: Getty Images
Kelsea Ballerini
Kelsea Ballerini
Photo: Getty Images
Alessia Cara in Nicholas Kirkwood shoes
Alessia Cara in Nicholas Kirkwood shoes
Photo: Getty Images
St. Vincent in Giambattista Valli Couture, Giuseppe Zanotti shoes, and Bulgari jewelry
St. Vincent in Giambattista Valli Couture, Giuseppe Zanotti shoes, and Bulgari jewelry
Photo: Getty Images
Ashlee Simpson in Georges Chakra Couture
Ashlee Simpson in Georges Chakra Couture
Photo: Getty Images
Charlie Puth in Prada
Charlie Puth in Prada
Photo: Getty Images
Camila Cabello
Camila Cabello
Photo: Getty Images
Teddy Geiger
Teddy Geiger
Photo: Getty Images
Rashida Jones
Rashida Jones
Photo: Getty Images
Tori Kelly
Tori Kelly
Photo: Getty Images
Nina Dobrev
Nina Dobrev
Photo: Getty Images
Diplo
Diplo
Photo: Getty Images
Quincy in Ermenegildo Zegna XXX
Quincy in Ermenegildo Zegna XXX
Photo: Getty Images
Catherine Shepherd and Brandi Carlile
Catherine Shepherd and Brandi Carlile
Photo: Getty Images
Lauren London in Le Vian jewelry
Lauren London in Le Vian jewelry
Photo: Getty Images
Andra Day
Andra Day
Photo: Getty Images
Swae Lee
Swae Lee
Photo: Getty Images
Shooter Jennings
Shooter Jennings
Photo: Getty Images
Ashanti
Ashanti
Photo: Getty Images
Andrew Wyatt and Anthony Rossomando
Andrew Wyatt and Anthony Rossomando
Photo: Getty Images
Jorja Smith in Balmain and Bulgari jewelry
Jorja Smith in Balmain and Bulgari jewelry
Photo: Getty Images
H.E.R. in Coach and Judith Leiber Couture bag
H.E.R. in Coach and Judith Leiber Couture bag
Photo: Getty Images
Jon Batiste in Coach
Jon Batiste in Coach
Photo: Getty Images
Chris Stapleton and Morgane Stapleton
Chris Stapleton and Morgane Stapleton
Photo: Getty Images
Fantasia Barrino
Fantasia Barrino
Photo: Getty Images
Bonnie McKee
Bonnie McKee
Photo: Getty Images
Wilmer Valderrama in Jimmy Choo shoes
Wilmer Valderrama in Jimmy Choo shoes
Photo: Getty Images
Ryan Hurd
Ryan Hurd
Photo: Getty Images
Patrizia Yanguela
Patrizia Yanguela
Photo: Getty Images
Donna Farizan
Donna Farizan
Photo: Getty Images
Shawn Everett
Shawn Everett
Photo: Getty Images
Nicolle Galyon
Nicolle Galyon
Photo: Getty Images
Emily Lazar
Emily Lazar
Photo: Getty Images
Merle Dandridge
Merle Dandridge
Photo: Getty Images
Tamara Dhia
Tamara Dhia
Photo: Getty Images
Buddy Guy
Buddy Guy
Photo: Getty Images
Bombino
Bombino
Photo: Getty Images
Lili Fini Zanuck
Lili Fini Zanuck
Photo: Getty Images
Keltie Knight
Keltie Knight
Photo: Getty Images
Karim Sulayman
Karim Sulayman
Photo: Getty Images
Raquel Sofia
Raquel Sofia
Photo: Getty Images
Roget Chahayed
Roget Chahayed
Photo: Getty Images
Mimi Saballa
Mimi Saballa
Photo: Getty Images
Lee Ann Womack
Lee Ann Womack
Photo: Getty Images
Claudia Brant
Claudia Brant
Photo: Getty Images
Gregory Porter
Gregory Porter
Photo: Getty Images
Fantastic Negrito
Fantastic Negrito
Photo: Getty Images
Sophie Hawley-Weld
Sophie Hawley-Weld
Photo: Getty Images
Falu
Falu
Photo: Getty Images
Lili Haydn
Lili Haydn
Photo: Getty Images
Alan Hicks
Alan Hicks
Photo: Getty Images
Isaac Cole Powell
Isaac Cole Powell
Photo: Getty Images
Jerry Cantrell
Jerry Cantrell
Photo: Getty Images
Tanika Ray
Tanika Ray
Photo: Getty Images
Derek Ali
Derek Ali
Photo: Getty Images
Ricky Rebel
Ricky Rebel
Photo: Getty Images
Renee Bargh
Renee Bargh
Photo: Getty Images
Tia Fuller
Tia Fuller
Photo: Getty Images
Etana
Etana
Photo: Getty Images
Jay Rock in Jason of Beverly Hills jewelry
Jay Rock in Jason of Beverly Hills jewelry
Photo: Getty Images
Charlie Wilson
Charlie Wilson
Photo: Getty Images
Kaskade
Kaskade
Photo: Getty Images
Toni Cornell
Toni Cornell
Photo: Getty Images
Raul Midón
Raul Midón
Photo: Getty Images
Ashley McBryde
Ashley McBryde
Photo: Getty Images
Hit-Boy
Hit-Boy
Photo: Getty Images
Evan LaRay
Evan LaRay
Photo: Getty Images
Ruth Westheimer
Ruth Westheimer
Photo: Getty Images
Mark Ronson in Celine by Hedi Slimane
Mark Ronson in Celine by Hedi Slimane
Photo: Getty Images
Sophie Milman
Sophie Milman
Photo: Getty Images
Blanca Blanco
Blanca Blanco
Photo: Getty Images
Vincent Watson
Vincent Watson
Photo: Getty Images
Kendra Erika
Kendra Erika
Photo: Getty Images
Aida Cuevas
Aida Cuevas
Photo: Getty Images
Tokimonsta
Tokimonsta
Photo: Getty Images
Tainy
Tainy
Photo: Getty Images
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