T-Pain recently stopped by the office to film the latest episode of Pushing Buttons. He and host Brian Farmer go toe-to-toe (or is that cup-to-cup) in the intense 2-D platformer “Cuphead,” an addictive, critically-acclaimed game that’s got buzz for its old-school cartoon graphics, upbeat jazz soundtrack, and staggering level of difficulty.

Surprisingly, the self-proclaimed “rapper ternt sanga” holds his own. He just released his latest album Oblivion, and also recently acquired the hotly-anticipated iPhone X. In case you missed it—make sure to check out T-Pain’s guide to using animojis correctly.

He also took some time to model some of the freshest looks of the season. Check out our exclusive editorial below, and get some advice on what to wear this season from the Grammy-winning artist.

Sunglasses: Off White x Warby Parker, Sweater: Maiden Noir, Shirt: Cav Empt, Sweater: Thom Browne

Let Your Sweater Make a Statement

‘Tis the season for ugly Christmas sweaters, but you can just as easily rock something with a little bit of pop that will look fresh into the new year. T-Pain wears a horizontal stripe sweater from Thom Browne and pairs it with sunglasses from Virgil Abloh’s Warby Parker collab. Note how the square frames provide an angular contrast with his face, resulting in a slimming effect.

Sunglasses: Billy Reid, Shirt: COMME des GARÇONS

Mix Up Your Shirt Game

COMME des GARÇONS has been doing patchwork everything for a long, long time. The classic button-down shirt is made instantly more covetable with a different mix of patterns, textures, and fabrics. Balance it out with solid colors underneath—the layered chains are optional, but still contribute to the overall flex.

Sunglasses: Billy Reid, Sweater: Maiden Noir, Vest: Chin Mens, Pants: Sacai

Switch Up the Slim Fit

Oversized garments may be all the rage these days, but you can’t deny how slim-fitting pieces still complement an overall minimal silhouette. Here, T-Pain rocks a striped Maiden Noir sweater with a more oversized, fashion-forward vest from Chin Mens. The result is a balance that looks next level, but doesn’t scream “fashion” with a capital “F.” The wider-leg Sacai pants also provide a welcome contrast to the more fitted sweater, without making him look like he’s drowning in the garments. It’s that kind of attention to proportion that shows you know what you’re doing.

Now see T-Pain in action in Pushing Buttons below:

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For more hilarious T-Pain goodness, check out the artist’s guide to using animojis correctly.

  • Photography: Thomas Welch
  • Photography Assistant: Bryan Luna
  • Styling: Corey Stokes
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