(after he wrapped the first leg with two sold-out shows at Radio City Music Hall in N.Y.C earlier this month). But the Texas-born singer-songwriter has something else to be excited about his first fashion campaign with Gap.

“Honestly, I used to watch the Gap commercials as a kid in the 90s and they were just the coolest. I loved how they were multicultural and music based and always felt sort of vibe-y and catchy,” the 29-year-old Grammy nominated artist, who is teaming up with the iconic American label for its 2018 holiday campaign, told PEOPLE.

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We caught up with Bridges to learn all about what it was like shooting his first campaign, his personal style aesthetic and more in honor of the star’s exciting new fashion gig.

What was the vibe like on set when you were shooting the campaign?

Super chill and easy. I was able to dance and sing and everyone on set was welcoming. It didn’t feel like work. I love dance and I prefer when dance is both choreographed but also felt out and spontaneous. I didn’t choreograph this one myself but we all got into a groove.

What’s your first memory of shopping at the Gap?

Going to the mall in high school and Gap being a must-stop destination.

What are holidays like in your family?

I tour the majority of the year so I like to go home to Fort Worth and spend time with my family. We are Texans, so lots of food!

What is your go-to holiday party outfit?

Oh man. You have to like what you are wearing or it doesn’t work. You can never go wrong with a good jacket, button down and well-tailored pants. I treated myself to a new leather jacket that has retro-ish stitching on it that I have been wearing that around to parties and stuff. I also like nods to Texas like bolos and boots.

What are three key pieces in your off duty wardrobe? How about your on stage wardrobe?

I have been wearing this cool knit hat I bought in Japan, denim overalls and I love the Dapper Dan Gucci collab.

You cover Gil Scott Heron’s passionate “Whitey On the Moon” in the highly acclaimed film, First Man. What was that experience like?

It was amazing. When I was on SNL Ryan [Gosling] was the host and he was super cool and very warm. He does a great job in this film. While he wasn’t on set the day I filmed, it was cool that we had that thread. I hope I did a good job because Gil really paved the way, and musicians have a lot to thank him for.

How did you prepare for the role?

I just listened to Gil on repeat. I thought about how brave he was to be a man of color speaking his mind and bringing awareness to important social issues during a tough time. Damien [Chazelle] was a good director too and made me feel welcome.

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Who is your dream duet?

Ginuwine, Drake, Usher, Migos – all great artists!

You’ve been nominated for some Grammys! How does awards hype affect you?

I like to look sharp especially since when you go to these events you are around the big dogs, so to speak. I always get lent beautiful suits and then I add my own touches to make them mine.

A whole new legion of fans were introduced to you on the Big Little Lies soundtrack with your song, “River” — were you surprised by all the love?

When I put my first album out and was touring smaller venues, Reese Witherspoon posted a picture of my album cover to her Instagram with a note about how she liked it. I couldn’t believe that this powerful woman was listening to my album and took time out of her day to do that. Literally, I had been washing dishes a year and a half earlier. So later on, “River” was synched in Big Little Lies and I was excited because everyone watches HBO and I thought how cool it was, knowing that Reese had heard my music before. My phone started blowing up after that scene aired and the label called to tell me “River” was selling and streaming like crazy. I love that people tag me in their wedding pics and say they walked down the aisle to “River.”