Brandon Maxwell is the genius behind iconic looks of famous celebrities like Lady Gaga, Oprah Winfrey and Meghan Markle, but to his mom, Pamela Woolley, he's still the little boy who grew up giving her fashion advice.
Woolley sat down with TODAY's Sheinelle Jones for our "Through Mom's Eyes" series to talk about watching her son's career take off.
"I made the mistake of storing my nice dresses in a closet next to his bedroom," Woolley said with a laugh. "He would take my dresses and redesign them and make them into whatever. ... I'm telling you, he was always critiquing what I was wearing. And believe me, I was asking 'Do these earrings look nice?'"
Woolley, who lives in Texas, said that the chaos of having so many children (Maxwell is the oldest of four) meant she often leaned on family for help. Her mother worked at a local boutique, and Maxwell spent plenty of time in the shop growing up.
"His school was literally around the corner from where my mom worked," Woolley said. "It was one of those stores where you can call and say, 'Hey, I need this outfit for this event,' and you walked in and she had a rack full. She had the outfit, she had the shoes, she had the earrings, she had the purses. You walked in, you got what you need, you left. And I think a lot of that love for what he does, designing clothes, came from that, watching my mom."
Woolley said that while Maxwell was surrounded by a supportive family growing up, he also battled insecurity.
"I think he questioned himself a lot," she said. "But ... he has said several times: 'Lean into who you are.' And he was always leaning, he was always moving in that direction, he was true to himself."
As a parent, she felt her most important job was to encourage her kids.
"You just reassure them, and you're positive," she said. "I always had the faith and belief in him, and I think he had it down. Of course, he had it in himself. You just have to remind him it's there, because it's always been there. You know as a parent what your child's gifts are."
Years later, Maxwell returned that support when his mother was diagnosed with breast cancer. Woolley told Sheinelle that all of her children surrounded her with "love and support." During New York Fashion Week 2019, Maxwell even dedicated his line to Woolley and the pair walked down the runway together.
"You have no idea," Woolley said of the emotions of that day. "His whole life flashed (in my mind) while we were walking down that runway. I was thinking of the day he was born and all the things we've been through, and I couldn't believe that he made his dreams come true. Just, my son was doing what he's meant to do ... thank goodness I made it. I didn't fall, but I was a crying mess."
Thankfully, Woolley's cancer is now in remission. She told Sheinelle that she's "moving out (and) doing great."
In addition to the emotional runway walk, Maxwell has dressed his mom on a number of other occasions. She wore her first Brandon Maxwell gown in 2016.
"I went a year seeing everyone else wearing Brandon, and I had never even slipped into a Brandon Maxwell outfit," Woolley told Sheinelle. "He surprised me with my very first (one) in June of 2016. I'll never forget. And it was absolutely gorgeous. And I felt so beautiful in it, you know?"
Woolley told Sheinelle that if she had one piece of advice for parents it would be to "pay attention to who (their children) are."
"Build on that, encourage that," she said. "If they're doing what they love and what their true self is and who they are, then they're going to be a success. ... Just let them be and just let them go and let them do their thing, and that's that. Just encourage."