I hadn’t been on a single date in nearly a year.
After ending an on-again, off-again seven-year relationship, a dating hiatus was a zen no-brainer. After all, I had a therapist and grainy Eras Tour livestream videos to keep me sane. So when I finally decided to end my self-partnered spree, I needed my reentry into the dating pool to be somewhat feral. They say grief has five stages, but as any recently single woman understands, there’s a sixth: revenge dressing.
Fortunately, 2024 was fashion’s Great Undressing™, with countless A-listers rocking one naked trend or another. While exposed thongs and freed nips were everywhere, nothing surpassed the appeal of going pantsless. Dua Lipa, Kendall Jenner, and Hailey Bieber have been the movement’s fearless leaders.
As a fashion writer and mere mortal, I figured it was my civic duty to test out the look. Armed with mere resolve and approximately zero prospects, I scoured my personal Rolodex for options. Ditching a key item of clothing with someone I already knew felt much safer than with a stranger. And if I was going to dress like some of the most confident women on the planet, the least I could do was channel some of that aplomb.
Emboldened, I slid into an acquaintance’s DMs and asked him out — something I’d never done before. My future pantsless alter-ego already had way more game than pants-wearing present me. She scored; he said yes.
Getting (Barely) Dressed
Though he initially picked a more upscale spot in New York’s Midtown, I countered with a Long Island City joint three minutes from my apartment. This style isn’t winter-friendly unless your commute is door-to-door. I started getting ready at 4:30 p.m. for our 7 p.m. date, which meant I was already running late. As I prepped, Chappell Roan’s “Naked In Manhattan” blasted in the background.
Despite my proclivity for a revealing look, I’ve always toned it down on first dates because I don’t trust dudes to get my non-traditional ‘fits. Since I was uncertain of how my date (let’s call him Mark) would react to such a risqué style, I did something I never do when getting dressed: commission a straight man’s POV.
“Too slutty?” I asked my roommate, as I modeled the tiniest red leather shorts over sheer black tights in the living room. (While I’d intended to raw-dog pantslessness, it was 47 degrees and raining; bare legs were not an option.)
“Too Mickey Mouse,” he said. Seeing his point, I changed into a pair of black leather Central Park West X Revolve hot pants. That was much more well-received. “He’ll love it,” he said.
The final look included a long-sleeved top and oversized coat both from Helsa, and knee-high Miista boots. Dread kicked in as I walked out the door. I’d been so focused on the ensemble, I forgot I actually had to go on the date. It didn’t help that I felt hella naked.
The Grand Reveal
Unveiling the outrageous look in front of Mark was definitely nerve-wracking, so much so that as I removed my coat, I spilled the entire contents of my purse, including some change and my precious Dunkin’ gift card. I was hoping we could sit at the bar for max visibility, but he was already seated at a table that blocked his view of the leather underwear. So I improvised a way to give the ’fit its due screen time.
Halfway through my dirty martini, the date going well, I excused myself to go to the restroom so I could flaunt the ensemble in all its revealing glory. When I returned, I asked, “What do you think of the outfit?” giving it a little spin. Asking the question with confidence was easy, but I wavered halfway through the pirouette and slumped back into the seat. Fortunately, the response was positive.
“I think it looks great,” he said — vague but still encouraging.
We Bonded Over The No-Pants Trend
A couple hours in and the conversation was still flowing, so, I suggested moving from the rustic bar to a more intimate second location, a Taiwanese speakeasy with great food — and, importantly, a romantic vibe. There, I sat cross-legged beside him, my pantsless situation on full display. Intrigued by the look, he brought it up again. I explained that the no-pants look was trending among fashion girlies.
His response shocked me. “Oh yeah, Hailey Bieber wears that,” he said. (He’s a fashion photographer, ICYWW.) As someone who’s previously had to explain who she even is, I found it refreshing (and a green flag) to connect in that way. I pulled up an example of her outfit, fully turning the conversation into a flirty fashion debate.
The date progressed from there. As someone who’s notoriously not touchy, I found myself lightly tapping his knee. I mean, my butt cheeks were already out, so YOLO. The no-pants look acted like a sort of confidence-boosting talisman. It was a tall order for such little fabric, but it worked like a charm.
Our six-hour date ended with a walk home and a goodnight kiss (let’s keep this PG for the sake of this story). “You must really like my outfit,” I said, flirtily. He agreed. “That’s because someone decided to go no pants.”
For the second date, I went braless. It was also a hit, and now, I’m brainstorming my look for date number three.
