What do a cherry red cowboy hat, the late R&B singer Aaliyah, and an old typewriter have in common? The hearts of some seriously major designers. This delightfully random assortment of things represents just a few of the answers we got after putting an ask out to five creative geniuses behind beloved American labels for the objects of their lifelong obsessions—and, of course, the full backstory. Brandon Maxwell, Bob Mackie, Tommy Hilfiger, Jason Wu, and Tory Burch have their eye on some pretty eclectic goods right now. Keep scrolling down for the surprising scoop on what the fashion stars you love, well, love.
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“Sometimes it’s hard, with things swirling around you, to remember to stay true to yourself. My grandmother Dot wore this hat, from Johnny’s Custom Hatters in Longview, Texas, with a red suit and matching cowboy boots. It sounds ridiculous, but in a way it was so chic. She did not give one single thought to what other people would say. It stood for the type of woman she was–extremely independent. When she passed in April, I decided to keep it in my office as a reminder. All my memories are of her being in an office all day working hard to create a business. Every time I saw her wear a fur coat or a diamond ring, it wasn’t in a flashy, extravagant way, so I knew this was something she must have really wanted, and that’s what I’ve always carried with me. No one buys a red cowboy hat because it’s a necessity.”
“I’m the first to admit I’m superstitious. I knock on wood, carry a red ribbon for good luck, and always travel with three gold bracelets that have my boys’ nicknames on them: Pickle, Hanky, and Saucy. Everyone in our family has a nickname—my brothers called me Toad. I had these bracelets made several years ago, inspired by my father, who designed jewelry for his mother and my mother. I love how they tell a story, like pieces passed down from my parents. My boys, once racing through our apartment on tricycles, are now young men, towering over me. Being their mom has been and always will be the greatest adventure and joy of my life. Whenever I put these bracelets on, I feel connected to them; they are the ultimate good-luck charms.”
Inspired by her own nickname bracelets, Tory Burch created new versions that say “Love” and “Divine.” (“ ‘Divine’ because my mother says it in nearly every sentence,” Burch says. “And ‘Love,’ well, that’s a given.”)
“I’ve been sewing ever since I was 9. My parents were avid antiques collectors, and when I was in my teens, my dad found this miniature sewing machine from the ’20s or ’30s on one of his travels in Europe. It doesn’t really work anymore, but it’s beautifully made. It’s very sentimental to me because it’s from my dad, from a time in my life when I was starting to discover who I wanted to be. But at the time I was like, ‘Why did you get me something so old?’ And yet this is the one thing I have kept with me over the years, from boarding schools to moving apartments three times in New York.”
“In the ’90s, Kidada Jones, daughter of music legend Quincy Jones, styled for the brand and kept an eye out for what was buzzworthy. She introduced me to a young R&B singer named Aaliyah. We paired her with then-up-and-coming DJ Mark Ronson for a photo shoot for the first Tommy Jeans campaign in 1996, and the rest is history. The ad became iconic, a symbol of our twist on American classics. Aaliyah was beautiful, talented, and had a bright, magnetic personality that drew everyone in. Today, over 20 years later, the laid-back cool look Aaliyah wore in the ad is still relevant, and she continues to be remembered as a style icon.”
Aaliyah appeared in the first campaign for Tommy Jeans wearing a bandeau top with these colorblock jeans.
“I guess if you wait around long enough, everything comes around again. I used to do tons of stuff for Elton John. I first worked with him for a TV special in 1975 with Bette Midler, Cher, and Flip Wilson. After it was over, he asked if I would do some things just for him, so I asked what he would like, and he said, ‘Like what you make for Cher–jumpsuits with holes in them and feathers.’ It was a sort of New Age Liberace look at that moment. Later on we did things a little more butch, but that was when he was thin and young. It’s funny—they do a sketch in that special where they’re at the old folks’ home playing old, like they’re in their 70s. And now they really are that age.”
For spring, Gucci creative director Alessandro Michele designed a capsule collection inspired by looks from Sir Elton John’s archives, including several that were originally created by Bob Mackie, like the above top.