I still remember running down Madison Avenue with a dress in my hands. Not casually walking. Running. Dodging taxis, weaving around people on the sidewalk, trying not to destroy a dress that had just been steamed and pressed. I have no idea how many blocks I ran that afternoon, but I remember being very aware of the time. I had about 25 minutes to get to an Express store, have a security tag removed, and make it back to the hotel before Trae Young's family left for the NBA Draft.

Yes. A security tag. On his mother's dress. Of all the things that could have gone wrong that day, somehow that was the one I hadn't planned for. And if I remember correctly, I made it back with about three minutes to spare. I handed the dress over, she got changed, and they were off. Just another completely normal day at work.

I've been thinking about that experience lately, mostly because draft night has become such a significant fashion moment in sports. We see the photographs, the suits, the jewelry, the athletes stepping onto the stage, shaking hands, holding up jerseys, and officially beginning the next chapter of their careers. Everything looks so polished. Which is funny, because I can tell you from experience that the hours leading up to those photographs can be anything but.

Back in 2018, I was working at Express, and we were preparing to outfit Trae Young and Mo Bamba for the NBA Draft. Two athletes on the same night, with two completely different sets of challenges and a whole lot of preparation. Mo, for example, presented a pretty obvious challenge before we even started talking about what he wanted to wear. He's seven feet tall, with an extraordinary wingspan, which makes finding a suit that fits him a little more complicated than walking into a store and pulling something off a rack.

We knew early on that we would need to plan ahead, take custom measurements, and figure out how to accommodate proportions that traditional suiting simply wasn't designed for. There was a lot of work involved in getting that right, including custom details and a special lining for his jacket. Trae was a completely different experience. He had a point of view about what he wanted to wear, and we knew we wanted to go in a more formal direction, something closer to a tuxedo. And then we got to the fitting.

Somewhere in that process, we decided the tuxedo would be better with shorts. Which, as you can probably imagine, wasn't exactly the most conventional choice for one of the biggest nights of a young athlete's career. There were conversations, approvals, and definitely a few nervous people back at the office. And there was a tailor and me, waiting in a hotel hallway for the final go-ahead to cut the pants. I wish I were exaggerating. We were literally on our hands and knees, marking where the trousers needed to be cut, knowing that once we made that decision, there wasn't much going back. When we finally got the approval, she was hand-sewing the shorts just before Trae needed to leave.

I think about that now and laugh, because when you see the finished look, you don't see any of that. You just see Trae. Which was exactly the point.

There was another part of Trae's draft experience that I remember just as vividly. Through conversations with his agent, we wanted to do something special involving his younger brother. The two were close, and we had this idea of creating a matching suit so his brother could surprise him after he was drafted. Simple enough, right? Except Express didn't make children's suits, and we needed the fabric to match exactly.

So we did what any perfectly reasonable group of people would do. We took five or six of the largest suits we could get in the same fabric and handed them over to a pattern maker. Her job was essentially to take apart already constructed adult suits, salvage the fabric, and rebuild everything into a completely new suit for a child. I remember her being cautiously optimistic. She thought she could pull it off, but there was no guarantee. And I didn't actually have the finished suit in my hands until the morning of the draft, which, looking back, was probably cutting things a little closer than I would have preferred.

But it worked. Trae's younger brother got to surprise him in a matching suit, and what could have been just another wardrobe detail became something personal to their family. That's the part I loved. The clothes were important, of course, but they were also a way to create a moment that meant something beyond what anyone was wearing.

I have another photograph from that day that I still think about. It's not one of the official draft photos. It's a picture of Mo Bamba, our producers, videographer, tailor, and me standing in what I remember being a back service hallway or stairwell at the hotel. We were trying to get him to a photo shoot without drawing attention, so we'd been moving through the back of the building. Everyone was hot, everyone was probably a little exhausted, and we're all smiling. Not because everything had been easy. Quite the opposite. I think we were just happy to have gotten to that point.

There had been so much preparation leading up to the day. Measurements, fittings, custom work, logistics, last-minute adjustments, and a hundred little decisions that nobody outside the room would ever know about. And there we were, standing in a service hallway, about to watch this young man experience something he'd probably been dreaming about for most of his life. I love that photograph, maybe even more than some of the finished ones, because it reminds me of what the experience actually felt like.

I think one of the things people misunderstand about styling, particularly when you're working with athletes or talent, is how much of the job has very little to do with clothes. Of course, the clothes matter. They matter a lot. But so does knowing the person you're working with. Understanding what makes them comfortable, what they're excited about, what they're nervous about, and when they need someone else to make a decision so they can focus on something more important.

On draft night, the last thing I wanted was for Trae or Mo to be worrying about a tailor, a missing garment, or whether something was going to fit. They had enough going on. Our job was to take care of everything we could so they could actually enjoy the experience. Even if that meant hand-sewing a pair of shorts in a hallway or running through Manhattan with someone's mother's dress.

There's something really special about being trusted with those moments, and I don't think I fully appreciated that at the time. I was so focused on getting everything done, making sure everyone was dressed, making sure the families were taken care of, and making sure nobody missed their bus. But looking back, I realize how much of the experience was about the relationships we were building.

I'd worked with both athletes before the draft and continued working with them afterward. I got to see them grow into their careers, become more comfortable with who they were, and develop their own sense of how they wanted to present themselves. Draft night was one moment in that process. A pretty significant one, but still just one moment.

And while I remember watching their names get called in the first round and seeing them walk across that stage, the memories that have stayed with me are a little different. A tailor on her hands and knees in a hotel hallway. A little brother in a suit that almost didn't exist. A group of us smiling in a service stairwell. And me, running down Madison Avenue with a dress in my hands, hoping I could make it back before the bus left.

Funny what you remember. I don't think I'd trade any of it.