Christopher Gilbert has never met a stranger. From the moment you ask about one of his brightly colored suits, he’ll tell you about his story and ask you about yours. The choreographer, teacher and self-proclaimed ambassador of local arts views his vibrant attire as a conversation starter about how much Milwaukee means to him. “We live in a visual world, and a lot of times people are like, ‘I don’t know his story, but I know he’s about something because of how he presents himself,’” he says. “I owe all of what I am today to Milwaukee, and it allows me to be my unapologetic self.”
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Going Big
These Stacy Adams spats remind Gilbert of the Harlem Renaissance and Michael Jackson. “I call them the Smooth Criminals,” he says, noting that they add a certain air of elegance to the look. “I don’t want my best-dressed day to be in a casket, so that means you got to go big every single day.”
Blazer First, Questions Later
The custom-made blazer was designed by a friend of Gilbert’s overseas, and the pants are a vintage find, part of a separate three-piece purple suit. His process: “I put on the blazer first, and then the pants came into the equation,” he says.
Statement Pieces
Gilbert’s accessories aren’t just decorative; every piece is intentional and symbolic. Take the brooches on his blazer’s lapel, for example: “The crown is at the top. … I teach dance to little girls and tell them to keep their crowns held high,” he says. “The glasses remind me to stay cool under any circumstance. … The scorpion represents to strike while the iron is hot … and the [treble clef] reminds me when you hit the right note, everything makes sense.”
Loving Local
Suits comprise over 95% of Gilbert’s wardrobe – 175 suits to be exact – and he wears them nearly all the time. The only exception is when he’s teaching dance; then, he’s sporting local brands like Unfinished Legacy – just one way he boosts the city, along with emceeing Summerfest and collaborating with the Milwaukee Public Library’s TikTok.
