It started as a joke over Sunday brunch. Megan was giving me that look—the one that says “I love you but what the hell are you wearing?”—as I sat across from her in what I thought was a perfectly acceptable combination of faded jeans and a vintage flannel I’d scored at a thrift shop in Williamsburg. I was defending my choices, as I always do, with my standard line about how menswear experts appreciate “considered dishevelment” when she put down her mimosa and said, “You know what would be funny? If you let me dress you for a week. Just to see what happens.”
Now, I should mention that my girlfriend works in PR for a luxury fashion brand. She spends her days surrounded by people who treat getting dressed like it’s performance art. Meanwhile, I write about men’s style for a living but have somehow cultivated what my boss once diplomatically called my “specific aesthetic”—a mix of classic menswear, vintage finds, and the occasional questionable experiment. I’m the guy who will pair a $900 sport coat with ten-year-old New Balances and think it’s the perfect high-low mix. Megan calls it my “professionally rumpled professor vibe.”
“Absolutely not,” I told her, spearing a piece of avocado toast. “There’s a conflict of interest here. I literally get paid to have opinions about men’s clothes.”
“Exactly,” she said, that mischievous glint in her eye. “Think of it as research. You’re always writing about guys stepping outside their comfort zones. When’s the last time you actually did that yourself?”
She had me there. The truth is, I’ve settled into my style over the years. I know what works for me—or at least what I think works for me—and I’ve built a wardrobe around those principles. The idea of surrendering that control was genuinely uncomfortable. Which, of course, meant I had to do it.
“Fine,” I said, already regretting it. “One week. But I get veto power if you try to put me in skinny jeans or anything with sequins.”
“Deal,” she said, clinking her glass against mine. “And no vetoes. That defeats the entire purpose.”
That night, Megan went through my closet like an archaeologist examining artifacts from a particularly unfashionable civilization. “How many blue Oxford shirts does one man need?” she asked, pushing hangers aside with increasing concern. “And why do you have the same gray sweater in what appears to be three slightly different shades of gray?”
“They’re completely different!” I protested. “That one’s charcoal, that’s slate, and the other is more of a heathered—”
“This is worse than I thought,” she interrupted, pulling out her phone to take notes. “I’m going to need to bring in some reinforcements.”
The “reinforcements” turned out to be a few pieces borrowed from her brother Michael (who, annoyingly, dresses like an Italian movie star despite working as an accountant) and two strategic purchases she insisted were “investments” rather than expenses. I tried not to wince when she came home with shopping bags. The experiment was getting expensive before it even started.
Monday morning arrived, and with it, the first outfit. Megan had laid it out on the bed like I was a kid on the first day of school: slim-cut navy chinos (mine, thankfully), a light blue button-up that I didn’t hate, and—here was the twist—a burgundy knit tie that I’d owned for years but rarely wore, plus a camel-colored cardigan instead of my usual navy blazer. The shoes were brown suede chukkas that had been sitting unworn in my closet since an ill-advised shopping spree three years ago.
“This isn’t that different from what I’d normally wear,” I said, relieved.
“Exactly,” she replied. “We’re starting with the shallow end before I throw you into the deep. But notice there’s no tweed, nothing frayed, and—most importantly—it all actually fits you properly.”
I rolled my eyes but got dressed. The pants were admittedly more flattering than my usual slightly-too-loose chinos. The cardigan felt soft and looked richer than my standard navy jacket. Looking in the mirror, I had to admit I looked more put-together than usual, though I’d never say that out loud.
Walking into the Style Authority office, I braced myself for comments. Our fashion team notices everything—a new haircut, different glasses, the slightest tweak to your usual look. Sure enough, Trevor from the digital team stopped mid-sip of his cold brew.
“New cardigan?” he asked, eyebrow raised. “Looks good, man. Very Brunello Cucinelli catalog.”
I mumbled something about “trying something different” and hurried to my desk, both pleased and slightly annoyed by the attention. But the real surprise came during the editorial meeting when our editor-in-chief, Daniel, actually stopped mid-sentence while discussing upcoming features to say, “Reed, you look especially sharp today. Like you’re actually taking your own advice for once.”
The office erupted in laughter. I felt my face flush but gave a little mock bow. “Thank my girlfriend,” I said. “She’s staging an intervention.”
Tuesday’s outfit pushed me further out of my comfort zone: gray dress pants (fitted more narrowly than I’d choose myself), a white Oxford (mine), a black knit blazer that felt surprisingly comfortable, and—the real shock—a pair of sleek black Chelsea boots I’d never have picked out myself. The overall effect was more modern, more metropolitan than my usual vintage-inspired look.
“You look like you’re going to fire someone,” said my colleague Lisa when I walked in. “But in a hot way.”
The strangest part was how differently people at work seemed to interact with me. Junior writers who normally just waved in passing stopped to ask my opinion on pitches. The marketing guy who’d been avoiding my emails about collaboration suddenly materialized at my desk, coffee in hand, ready to talk strategy. Even the front desk security guard gave me a “Looking sharp, Mr. Reed” instead of the usual nod.
I texted Megan at lunch: “People are acting weird. I think you’ve turned me into Patrick Bateman.”
She replied with a laughing emoji and: “That’s just how people treat guys who look like they have their shit together.”
Wednesday’s look nearly broke me. Megan had pulled out a pair of olive green pants that were—and there’s no gentle way to put this—significantly more fitted than I’d normally wear. “These are basically skinny jeans,” I protested as I struggled to get them on.
“They’re just regular pants that actually fit,” she countered. “Most men wear everything two sizes too big. You’re drowning in fabric half the time.”
She paired them with a simple black t-shirt (admittedly the softest one I’ve ever worn—some Japanese brand I’d never heard of), a light gray unstructured blazer, and clean white sneakers. The overall effect was roughly 70% more fashionable than I’d normally dress, and about 40% less comfortable—at least psychologically.
I felt self-conscious walking into the office, certain I looked like I was trying too hard. But something interesting happened. Rather than mockery, I received genuine compliments. The senior style editor—a guy who regularly attends Paris Fashion Week and once made an intern cry by criticizing his loafers—actually stopped me in the hallway.
“This is a good direction for you,” he said, gesturing vaguely at my outfit. “More contemporary. You should consider featuring this kind of look in your column.”
The real surprise came that afternoon when Daniel called me into his office. I assumed it was about the feature I was working on for the September issue. Instead, he closed the door and offered me a promotion—style director for the print magazine in addition to my digital role. It came with a not-insignificant raise and considerably more influence over the publication’s visual direction.
“I’ve been thinking about this for a while,” he said, “but seeing you freshen up your look this week convinced me you’re ready to help guide our overall aesthetic. You understand classic style but aren’t stuck in the past.”
I walked out of his office in a daze and immediately called Megan.
“You’re not going to believe what just happened,” I told her.
“Your boss finally realized you’re brilliant?” she asked.
“My boss gave me a promotion and specifically mentioned my outfit. What kind of twisted social experiment are you running here?”
She laughed. “I told you clothes matter! And you write about this for a living!”
Thursday and Friday continued the experiment. Thursday was a monochromatic look—all black everything, from jeans to t-shirt to bomber jacket—which felt simultaneously out of character and ridiculously easy to pull off. Friday was what Megan called “elevated casual”: dark jeans, a washed chambray shirt, and a textured sport coat in a subtle check pattern that I actually owned but rarely wore.
By Friday afternoon, I’d received more compliments on my appearance in a single week than in the previous six months combined. A senior editor from GQ who was visiting our office for a collaboration actually asked where I’d gotten my jacket. My neighbor in the elevator, who’d never spoken to me before despite living on the same floor for two years, struck up a conversation. The barista at my regular coffee shop gave me a free pastry “just because.” The world was treating a slightly-better-dressed version of me noticeably better.
Over dinner Friday night, I reluctantly debriefed with Megan.
“Fine, I admit it,” I said, sipping my bourbon. “The experiment worked. People responded differently. But isn’t that a little depressing? That something as superficial as slightly more fitted pants could change how I’m perceived professionally?”
Megan considered this, twirling pasta around her fork. “I don’t think it’s that they like you better because you’re more stylish. I think it’s that you were telegraphing something different about yourself. More current, more adaptable, more aware of how you’re presenting. Those are qualities people respond to in any context.”
She had a point. And the truth is, by Friday I wasn’t even feeling self-conscious anymore. The slightly more tailored fit, the contemporary silhouettes—they had started to feel normal. Comfortable, even.
“So,” she said, “what did you learn from this very scientific experiment?”
I thought about it. “That my girlfriend is annoyingly right sometimes. That people—even style professionals—judge books by their covers more than they admit. That I’ve been playing it safe with my own style while telling readers to take risks. And that a good tailor is worth their weight in gold.”
She smiled. “And?”
“And I’m keeping the Chelsea boots. They make me feel tall.”
The following Monday, left to my own devices, I stood before my closet pondering what to wear. I reached for my usual uniform—well-worn chinos, Oxford shirt, tweed jacket—then hesitated. Instead, I grabbed the olive pants, paired them with a white Oxford and the gray blazer, then added a patterned pocket square that Megan had introduced to the mix.
Looking in the mirror, I saw a version of myself that felt both familiar and refreshed. Not a total style overhaul, but an evolution. A slightly more current take on my personal aesthetic.
I texted Megan a mirror selfie before heading out the door. Her response came seconds later: “Look who’s a quick study. But we need to talk about that pocket square folding technique…”
Some habits die hard. But I’ve kept the promotion, the boots, and the slightly more fitted pants. And I’ve gained a new perspective for my column—sometimes the person who most needs a style intervention is the one giving the advice. Now excuse me while I go write about the transformative power of letting someone else dress you. After I change into something my girlfriend would approve of, of course.
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