You know those couples on Instagram who seem to have a freakish level of style synergy? The ones who somehow manage to look coordinated but not matching, complementary but not identical, like they’re both the main character in the same aesthetically-pleasing indie movie? Yeah, that’s not me and Jake. Not even close.
Jake is what I’d charitably call a “functional dresser.” The man has worn the same style of Carhartt work pants for so long that I’m pretty sure his thighs have permanently molded to their specific cut. His t-shirt rotation consists exclusively of faded band shirts from concerts he attended in college and plain black Hanes that he buys in packs of twelve. He owns exactly two sweaters—both gifts from me—and wears them only when I employ what he calls my “fashion pout.” His idea of dressing up is putting on the one button-down shirt he owns that isn’t flannel.
Meanwhile, I have a clothing rack in our bedroom that’s bowing under the weight of vintage finds, sample sale scores, and what Jake refers to as my “fancy person clothes.” I plan my outfits the night before, have strong feelings about seasonal color palettes, and once cried actual tears over a pair of sold-out Rachel Comey clogs that I still occasionally search for on resale sites after a glass of wine.
We are, to put it mildly, at opposite ends of the style spectrum. Which is why, when my editor suggested I let Jake dress me for an entire week as a “fun content experiment,” my immediate reaction was nervous laughter followed by something close to panic. Let the man who considers clean sneakers a fashion statement choose my outfits for seven days? Including my outfit for an important advertiser meeting? And a dinner with fashion industry friends? What fresh hell was this?
But I’m nothing if not committed to the cause of fashion journalism. And if I’m being completely honest, I was secretly curious. Jake has actually complimented some of my outfit choices over the years (rare, notable occasions that I mentally catalog), but he’s also looked genuinely baffled by others. What exactly would he put me in, given free rein over my wardrobe? Would it be a fashion crime scene, or might he actually have some untapped style intuition?
So I agreed to the experiment, with two ground rules: First, he had to choose from clothes I already owned (no sending me out in one of his t-shirts as a joke, which I knew would be his immediate instinct). Second, I got veto power over anything that would actually get me fired or disowned by the fashion community. Otherwise, I’d wear whatever he selected, no complaints, for seven full days.
The night before Day One, I watched with a mixture of amusement and horror as Jake stood in front of my open closet with an expression usually reserved for people disarming bombs in action movies. He tentatively pushed hangers back and forth, occasionally pulling something out, squinting at it, then putting it back with a muttered “What even is this?”
“Take your time,” I said, perched on the edge of our bed. “This is actually going to be interesting.”
He shot me a look. “For you, maybe. For me, it feels like that nightmare where you have to take a test you didn’t study for. Except the test is your entire career.”
After about twenty minutes of increasingly frustrated browsing (during which I heard him mumble “Why are there so many black things that all look exactly the same?”), he finally assembled an outfit and laid it on the chair with a triumphant “Done!”
I examined his first creation: my most faded, comfortable boyfriend jeans, a plain white t-shirt, and—surprisingly—a structured navy blazer I’d found at a vintage shop in Boston. For shoes, he’d chosen my well-worn Adidas Stan Smiths.
“This just looks… normal,” I said, not sure if I was disappointed or relieved. “It’s actually not bad.”
“Don’t sound so surprised,” he said, rolling his eyes. “I’ve watched enough Project Runway with you to pick up a few things. This is like, casual but put together, right? The fancy jacket makes the casual stuff look intentional.”
I stared at him. “Did you just use the phrase ‘casual but put together’? Who are you and what have you done with my boyfriend?”
“Just put it on,” he said, looking pleased with himself.
Day One’s outfit was, I had to admit, perfectly fine. Better than fine, actually. I got compliments from two colleagues who had no idea I was conducting an experiment, and the jeans-tee-blazer combination was comfortable enough for running between meetings while still looking like I’d made an effort. When I texted Jake a mirror selfie from the office bathroom, he responded with a GIF of someone taking a bow.
But I knew we were still in safe territory. Those were all pieces I wore regularly, just not necessarily together. The real test would come with Day Two.
The next morning, I watched nervously as Jake returned to my closet with slightly more confidence, rummaging through drawers I didn’t even know he knew existed.
“How about this?” he said finally, holding up an outfit I would never—and I mean NEVER—have put together myself: a midi-length pleated skirt in a metallic bronze that I’d bought for a holiday party two years ago, paired with a simple black cropped sweater, and—the truly wild card—my chunky black combat boots.
“Jake. That skirt is formalwear. Those boots are for weekends. This makes no sense,” I said, already imagining the horrified stares of the fashion department.
“You said no vetoes unless it would get you fired,” he reminded me, looking annoyingly pleased with himself. “Will this get you fired?”
“No, but—”
“Then put it on. Trust the process.”
I grudgingly complied, fully expecting to look like I’d gotten dressed in the dark. But when I looked in the mirror, I was shocked. The combination of the fancy skirt with the edgy boots created this unexpected contrast that was actually… cool? The simple black sweater balanced the statement pieces, and the whole thing had this high-low mix that looked intentional rather than confused. It was something I might have seen on a street style blog and thought “I wish I could pull that off” without ever trying it myself.
“This is actually good,” I admitted, turning to see it from different angles. “Like, really good. How did you know this would work?”
He shrugged. “You always wear that skirt with those strappy heels that look painful, and you always end up complaining that your feet hurt. The boots looked comfortable. And I’ve seen those fashion people you follow on Instagram wearing fancy dresses with clunky shoes. It’s a thing, right?”
It was indeed “a thing,” and the fact that Jake—my flannel-wearing, fashion-indifferent boyfriend—had picked up on this trend through sheer osmosis was both impressive and slightly alarming. Had he been paying more attention than I thought all those times he nodded blankly while I rambled about runway shows?
Day Two’s outfit earned me a raised eyebrow and “Interesting choice” from our fashion director—the equivalent of enthusiastic praise in her understated lexicon. The office admin asked where I’d gotten the skirt, and two people in the elevator commented on my boots. I felt oddly conspicuous but also strangely liberated. By letting Jake make the choices, I was freed from my own self-imposed style rules and overthinking.
I reported the day’s success to Jake over dinner, trying not to sound too shocked. “People actually liked it. Multiple people.”
“Of course they did,” he said, looking smug. “I’m a natural. This is my calling. I’m quitting my job to become a stylist.”
“Don’t get ahead of yourself,” I warned. “We still have five days to go.”
Days Three and Four continued the surprising streak of successes. Jake put me in combinations I would never have considered: my wide-leg cream trousers with a vintage concert t-shirt I usually only wore to bed; a floral wrap dress I typically saved for summer weddings paired with a chunky cardigan and sneakers for an unexpectedly casual take. Each time, I’d initially protest, then reluctantly admit that the outfit actually worked.
“You’re overthinking everything,” he explained when I asked how he was doing this. “You have all these rules in your head about what goes with what, what’s work-appropriate versus weekend versus whatever. I’m just picking things I like together.”
It was true. I realized I’d developed a complex internal categorization system for my clothes: work pieces versus weekend pieces, high-end versus casual, statement items versus basics. Jake, unencumbered by these arbitrary divisions, was freely mixing across categories, creating combinations I’d never considered because I’d mentally filed the individual pieces in separate compartments.
Day Five brought our first major misstep. In his growing confidence, Jake selected an aggressively clashing combination: a leopard print skirt with a striped top in colors that fought violently with each other, topped with a denim jacket that added a third competing pattern. When I emerged from the bathroom wearing this cacophony of styles, even he winced.
“Yeah, that’s not it,” he admitted. “You look like you escaped from a circus designed by someone colorblind.”
“This is legitimately terrible,” I agreed, failing to suppress my laughter. “I can’t wear this to work. I’m invoking my veto.”
“Fair enough,” he conceded. “Let me try again.”
His second attempt was much more successful: simple black jeans, a white button-down, and a colorful scarf I’d forgotten I owned tied at my neck. Basic but polished, with just enough personality from the vintage silk scarf.
Day Six was the big challenge: an important dinner with friends who work in fashion, including a buyer from Nordstrom and a stylist whose Instagram I had religiously followed for years before we actually became friends. If ever there was a time I needed to look like I knew what I was doing fashion-wise, this was it.
Jake took the task with unexpected seriousness, spending nearly forty-five minutes creating different options before settling on one. His final selection was my black silk slip dress—a safe choice I often defaulted to for evening events—but with an unexpected twist: he layered it over a tissue-thin white turtleneck I usually wore on its own in warmer weather.
“The layering makes it more interesting,” he explained, sounding suspiciously like someone who’d been reading fashion blogs on his lunch break. “And it’s cold out, so you won’t freeze.”
He completed the look with my chunky-heeled ankle boots and a vintage brooch pinned at the neck of the turtleneck—a family heirloom I kept in my jewelry box but rarely wore because it felt too precious.
“The pin was my grandmother’s,” I said, surprised he even knew it existed.
“I know,” he replied. “You told me the story when you showed it to me last year. It’s special but you never wear it. Why have special things if you’re saving them for some theoretical future occasion that never comes?”
It was a surprisingly insightful question from someone who wore the same hoodie three days a week.
The dinner outfit was a genuine hit. My fashion friends immediately noticed the brooch, demanding to know its history. The layered slip dress prompted a discussion about 90s minimalism and its current revival. Nobody suspected these styling choices weren’t my own, and I found myself relaxing into a confidence that came from wearing something that felt both authentic to my style but pushed slightly beyond my usual boundaries.
By Day Seven—the final day of our experiment—I was actually looking forward to seeing what Jake would choose. He’d proven himself surprisingly adept at creating outfits that honored my personal style while challenging my self-imposed limitations. For our final day, which was thankfully a Sunday with no professional obligations, he went comfortable but deliberate: my favorite vintage Levi’s, a cashmere sweater in a rich burgundy that I typically “saved for special occasions” (another arbitrary rule he’d identified and dismissed), and my most beaten-up leather jacket.
“This just looks like my normal style,” I observed.
“Exactly,” he said. “It is your style. These are all things you love but don’t always wear together, or you save them for some reason that doesn’t make sense. The point isn’t that I created some wild new look for you—it’s that you already have a great style when you stop overthinking it.”
It was a surprisingly profound observation from someone who had, just a week earlier, been completely intimidated by the contents of my closet.
As our experiment drew to a close, I found myself reflecting on what I’d learned by temporarily outsourcing my fashion choices to someone who, by his own admission, “just wants to be comfortable and not naked in public.”
First, I’d been operating under far too many self-imposed rules about what “went together” and what didn’t. Pieces I’d mentally categorized as “not for work” or “only for special occasions” were actually versatile enough for multiple contexts when I stopped putting them in boxes.
Second, I’d been saving too many of my favorite pieces for some undefined “perfect occasion” that rarely materialized. My nicest sweaters, my most special vintage finds, my family heirloom jewelry—all were sitting largely unworn because I was treating them as too precious for everyday life.
Third, and most surprisingly, Jake had been paying far more attention to my personal style than I’d given him credit for. He’d absorbed more than I realized during our years together, developing opinions and observations about fashion that he rarely expressed but nonetheless had formed.
“So what did you learn from this little experiment?” I asked him on that final evening, as I returned to the closet that was now officially back under my control.
He thought for a moment. “Honestly? That fashion isn’t as intimidating as I thought. It’s not about following some complicated set of rules that only insiders know. It’s just about putting things together that make sense for the person wearing them.” He paused. “Also, that you own way too many black tops that all look identical to me but are apparently completely different in ways I’ll never understand.”
Fair enough.
As for me, I emerged from the week with a shifted perspective on my own wardrobe. I found myself reaching for combinations I wouldn’t have considered before, wearing my “special” pieces for ordinary days, and generally approaching getting dressed with a lighter touch.
I also gained a new appreciation for my fashion-indifferent partner, who proved to have a surprisingly good eye and an intuitive understanding of what makes an outfit work. He’ll never be the guy who gets excited about runway shows or understands why I need four different black blazers, but he sees me more clearly than I realized.
“Would you ever let me dress you for a week?” I asked as we got ready for bed that night. “Fair is fair.”
He looked genuinely alarmed. “Absolutely not. I know my limitations, and I’ve seen the wilder parts of your closet. You’d have me in those drop-crotch pants you love within 24 hours.”
“They’re avant-garde Japanese menswear, and they’re comfortable!” I protested.
“They look like I’m wearing a denim diaper, and you know it,” he countered. “I’ll stick with my Carhartts, thanks.”
Some style boundaries, it seems, are still meant to be respected. But maybe next time I’ll at least get him to try the black Carhartts instead of the tan ones. Baby steps.