Hailey Baldwin checks off a lot of #goals boxes. Not only is she a professional hot person, who happens to be dating Justin Bieber, but she also spends a lot of time doing cool things with her cool friends. A newish trend amongst her fancy friend group, which includes both Kendall and Kylie Jenner, as well as actress and model Ruby Rose, is to be close to the action at various sporting events. Just last week, Baldwin attended a New York Knicks game accompanied by ½ of Public School design duo Maxwell Osbourne. She wasn’t decked out in face paint with pom poms in her pigtails like the girls on the jumbotron; instead, she wore black leather leggings and a destroyed grey sweatshirt that hung loosely off her toned and tanned shoulders. Sexy? Yes. Sporty? Not really. But did she look good? Absolutely.
As someone who does not actively follow sports, but enjoys exclusive experiences, attending sporting events as Baldwin does is one of the more desirable recreational pastimes. Of course, I am not talking about being a bleacher creature at Yankees Stadium chugging beers and binging on hotdogs and nachos—the thing about Baldwin and her approach to the 40-yard line is that sporting experiences can be made chic. Thus, when New Era invited me to tag along with her to the Super Bowl this year, I was ready to be schooled.
We begun our Super Bowl extravaganza on Friday afternoon with lunch at the Battery in San Francisco, an exclusive members-only club. Hailey rolled up with her hair in two braids, a white t-shirt, leggings, a bomber jacket, and sneakers. Curiously, I had worn this same look on the plane and, incidentally, I’m flying back to NYC wearing a variation of the same thing. Since I am one of the few women sporting leggings (even though I am confident they look cool), I am curious to get Baldwin’s thoughts on the recent leggings backlash. She thinks carefully before answering, “Leggings are a comfortable form of pants, but yoga pants are yoga pants. It’s a separate thing. It’s got its own lane. Good for yoga pants.” So the leggings can stay for now, but probably won’t make the cut for the Super Bowl look. Baldwin says, “I like to be comfortable. I feel like girls overdo it sometimes and they get so dressed up for a sporting event. I like to be courtside and just be chilling.” Yea, dressing up...eww.
After lunch it was time to step into New Era’s swanky penthouse lounge where professional athletes are rubbing shoulders with models and chowing down on chicken wings with party goers participating in a version of Spike TV’s Lip Sync Battles, IRL. Before stepping upstairs, Baldwin made a quick costume change, and by quick, I mean she changed up her hair, makeup, dress, and shoes. “I will get dressed up for a game if I feel it necessary,” she says.
At the party, Baldwin spends time taking photos with New Era’s limited edition Super Bowl hat. The topper, which is all leather, features an 18k gold pin on the front and costs a cool $2500. “I like to throw on a hat,” she says. “Hence, New Era.” Yes, of course, we will just “throw on” hats that are more than the monthly rent of my Manhattan apartment. After tiring of her pricey hat, Baldwin makes her rounds elsewhere in the lounge, bypassing the customizable denim bar, but pausing to take selfies with the on-site hair and makeup artists. Just to paint the scene, Serena Williams breezes past and some other super famous athletes, who I don’t recognize, but people seem genuinely excited about.
The next day, I wait for Baldwin to show up at the New Era party at the Battery. This time we’re in the restaurant below, which they have cleared to make space for a stage for Future and Diplo to perform. She’s upstairs in her “glam chair”, getting primped before she’s set to walk the red carpet. Baldwin’s boyfriend is rumored to be arriving by boat via Treasure Island. This is for real. He actually showed up for his lady and they spend the remainder of the night cuddled behind the DJ booth. Baldwin emerges an hour behind schedule, but swears to me that she is low key. “I honestly don’t like to wear a lot of makeup, unless it's for something,” she says. “I don’t take very long to get ready. I’m a simple girl. Tops 30 minutes [to get ready], maybe 45 if we’re pushing it, get out the shower, blow dry the hair, sometimes straighten it, a little concealer, a little foundation, no mascara, and a good lip. That’s it.” Even though she’s a bit creative on her timeline, I can’t deny that she is working it in a super sexy House of CB dress, Stuart Weitzman heels, and layered body chains. I’m wearing a thinly-strapped bodysuit with a super low back that I have a feeling might recreate Janet Jackson’s notorious wardrobe malfunction at the 2004 Super Bowl if I’m not careful. But this issue isn’t entirely relevant as Baldwin tells me that, after all the weekend’s festivities, she’s not even attending the game.
“Well I have to go back for work,” she says. “It’s New York Fashion Week.” Um, no kidding! For me too...but I will definitely not be missing a Beyonce concert. Still, I think there’s at least one more thing to learn from her. I probe her for advice about how to maintain dignity in our precarious outfits for the night.
She replies, “Just be conscious and you got to keep panties on.” Ok...noted.