I Spent $400 Copying My Grandfather’s Wardrobe and Now I’m the Coolest Person in Finance

There’s this photo on my mom’s mantelpiece back in Atlanta – my great-grandfather in 1985, standing outside his church in his Sunday best. High-waisted pleated pants, suspenders, a cardigan buttoned all the way up, and these massive orthopedic shoes that honestly looked like something NASA designed. For years, whenever I’d see that photo during holiday visits, I’d think “God, I hope I never give up that hard on looking good.”

Cut to last month when I’m grabbing coffee before work near Downtown Crossing, and I see this group of what are clearly Harvard MBA students – you can spot them from a mile away – and they’re all dressed exactly like great-grandpa minus the church shoes. I’m talking pleated trousers hiked up to their natural waists, cardigans, even suspenders on one kid. And the thing that really messed with my head? They looked incredible. Not like they’d given up, but like they’d figured something out the rest of us were missing.

I literally stopped mid-sip and stared because these weren’t fashion casualties. These were the type of twentysomethings who probably have trust funds and definitely know what’s cool before it hits Instagram. One of them was wearing wire-rimmed glasses and a sweater vest that probably cost more than my monthly parking garage fee, and somehow he looked like he should be photographed for GQ rather than collecting social security.

You know what I did? I texted my younger sister Maya who works in tech and always knows about trends approximately six months before I do. “Are people seriously dressing like elderly men on purpose now?” I sent her a sneaky photo of sweater vest guy ordering his oat milk cortado.

“FINALLY you noticed,” she texts back immediately. “It’s called grandpacore and it’s been everywhere. I literally bought suspenders last week.”

Maya. Suspenders. The same person who once told me my Ann Taylor blazers made me look like I was “cosplaying a 2007 businesswoman.” She’s now voluntarily wearing suspenders to her tech startup job where half her coworkers show up in hoodies and yesterday’s jeans.

Once I started paying attention, I realized this whole grandfather aesthetic had completely taken over Boston’s younger professional crowd. The guys at the coffee place I go to every morning? Suddenly they’re all wearing these chunky New Balance sneakers that look exactly like the ones my dad wears for his weekend walks, except these probably cost three times as much. The women are doing it too – high-waisted pleated pants, oversized cardigans, loafers that scream “I prioritize comfort and arch support over everything else.”

I became obsessed. Like, genuinely obsessed in a way that probably wasn’t healthy. I started noticing it everywhere – the Financial District, Back Bay, even in my own office building. These aren’t people who’ve given up on fashion, these are people who are clearly very intentional about their choices. And they all look amazing in this weird, anti-fashion fashion way that I couldn’t stop thinking about.

So obviously I did what any reasonable person would do – I cornered the barista at my usual spot, who’s maybe 24 and has been progressively dressing more and more like he’s about to retire to Florida. His name’s Josh, and last Tuesday he was wearing pleated khakis, a cardigan over a button-down, and loafers that my podiatrist would absolutely approve of.

“Okay, I have to ask,” I said while he was making my usual. “What’s with the grandfather clothes? Are you doing this on purpose?”

Josh lit up like I’d asked him about his favorite hobby. “Oh yeah, totally intentional. I call it my ‘advanced age’ look.” He gestured down at his outfit. “There’s something really freeing about wearing clothes that aren’t trying to be sexy or edgy, you know? Plus everything fits better when you’re not trying to show off your body.”

He had a point. The pleated pants actually gave him this really elegant silhouette, and the cardigan looked expensive and thoughtful rather than frumpy. “Also,” he continued, “most of this stuff is thrifted or vintage, so it’s sustainable. And it lasts forever – these clothes were designed for men who needed their pants to survive decades of daily wear.”

The sustainability angle hadn’t occurred to me, but it makes perfect sense. My great-grandfather probably wore the same five outfits in rotation for twenty years. Meanwhile I’m over here buying new work clothes every season because the quality is trash and trends change every five minutes.

I started researching this whole phenomenon because, let’s be honest, I was wondering if I was losing my mind or if this was actually a real thing happening. Turns out it’s incredibly real and has been building for months. Fashion people are calling it everything from “grandpacore” to “gentle masculinity” to “comfort luxury,” but whatever you call it, it’s definitely a movement.

The more I thought about it, the more it made sense. We’re all exhausted from trying to look perfect all the time, right? Instagram fashion is so high-maintenance and focused on being photographable. There’s something really appealing about clothes that prioritize comfort and practicality over looking hot or trendy. Plus, in corporate environments like mine, this aesthetic actually works better than a lot of current trends – it reads as professional and put-together without being try-hard.

I’ll be totally honest – I started incorporating some of these elements into my own wardrobe, and the results have been… interesting. I bought these high-waisted pleated pants from J.Crew (okay fine, they were $180 but they’re really well-made) and paired them with a fitted turtleneck and loafers. The first day I wore this combination to work, three different people complimented my outfit. Three! In finance! Where the usual response to fashion choices is polite silence!

The pants are genuinely the most comfortable work clothes I’ve ever owned. They’re roomy without being baggy, the pleats actually create a really flattering silhouette when you tuck in a slim-fitting top, and the high waist makes my legs look approximately three miles long. I felt like I’d discovered some kind of fashion cheat code.

Then I went down the rabbit hole completely and bought a cardigan. Not just any cardigan – a really beautiful merino wool one from this brand called Folk that definitely cost more than it should have, but whatever. The first time I wore it buttoned all the way up over a collared shirt, I felt like I was playing dress-up as someone’s grandfather. But when I looked in the mirror? It actually looked really sophisticated and intentional. The oversized fit balanced the fitted pants, and somehow the whole combination looked more expensive than the sum of its parts.

My coworker James, who’s usually pretty reserved about fashion commentary, stopped me in the hallway and said, “That’s a great look on you. Very put-together but not trying too hard.” Coming from someone who wears the same gray suit rotation every week, this was basically equivalent to a standing ovation.

The shoes were my next experiment. I’d been watching all these young guys in my neighborhood wearing chunky New Balance sneakers – the 990s specifically – and they looked so different from how I remembered those shoes. These weren’t sad dad sneakers anymore, they were somehow… cool? I bought a pair in gray (they were $185, which feels insane for sneakers but they’re supposedly built to last forever) and started wearing them with my work outfits.

Game changer. They’re incredibly comfortable for walking around the city, they look intentional rather than lazy, and they add this interesting casual element to otherwise formal outfits. I’ve been wearing them with everything from suits to dresses, and they work surprisingly well. Plus my feet don’t hurt at the end of long days, which honestly might be worth the price alone.

The accessories are where this trend gets really specific. I bought wire-rimmed glasses even though my vision is fine (I know, I know, but they have clear lenses and they complete the look). I got a leather watch with an actual strap instead of my usual Apple Watch. I even bought a bucket hat, though I’ll admit I haven’t worked up the courage to wear it to the office yet.

But here’s what I’ve realized about this whole aesthetic – it’s not actually about dressing like an elderly person. It’s about adopting the parts of that style that prioritize comfort, quality, and practicality over trends and sex appeal. When you take grandfather clothes and style them with contemporary proportions and good fit, they look sophisticated rather than frumpy.

The key is in the execution. The pleated pants need to actually fit well through the waist and leg, not just be baggy everywhere. The cardigans should be oversized but structured, not shapeless. The shoes should be chunky and comfortable but still well-made and intentional-looking. It’s about taking the comfort-first philosophy of elderly fashion and applying it with a young person’s attention to fit and styling.

I’ve spent probably close to $400 building out this grandfather-inspired work wardrobe, and honestly? It’s some of the best money I’ve spent on clothes in years. Everything is incredibly comfortable, it all works together, and I get more compliments now than I did when I was trying to follow conventional work fashion rules. Plus, most of these pieces are classic enough that they’ll still look good in five years, which is more than I can say for most of my previous fashion purchases.

The weirdest part is how this aesthetic has affected how I feel at work. There’s something really confident about wearing clothes that aren’t trying to be sexy or attention-grabbing. I feel more focused on actual work rather than worried about whether my outfit is appropriate or fashionable enough. It’s like the clothes give me permission to be taken seriously for reasons other than how I look.

My sister Maya visited last weekend and immediately noticed my fashion evolution. “You’re doing the grandpa thing!” she said when she saw my Saturday outfit of pleated pants, cardigan, and chunky sneakers. “It looks really good on you. Very ‘I have my life figured out’ energy.”

That’s exactly what it is. This aesthetic projects competence and intentionality without being flashy or try-hard. In corporate environments especially, it hits this sweet spot of being professional enough for conservative dress codes while still showing personal style and thoughtfulness about clothing choices.

I think what appeals to me most about this trend is how it rejects the constant pressure to look young and conventionally attractive that dominates most fashion advice. There’s something quietly rebellious about choosing comfort and practicality over what’s supposed to be flattering or sexy. It’s fashion for people who have more important things to think about than whether their clothes are Instagram-worthy.

Of course, like any trend, it can go too far. I’ve seen people who look like they’re literally wearing costumes rather than incorporating these elements thoughtfully. The goal isn’t to look like you’re actually eighty years old, it’s to borrow the best parts of that aesthetic – the comfort, the quality, the practicality – and style them in a contemporary way.

But when it’s done right? It’s honestly brilliant. I feel more confident, more comfortable, and more authentically myself than I have in any work wardrobe I’ve ever put together. And apparently I’m not alone – this trend is spreading through professional environments everywhere, probably because it solves so many of the problems with conventional work fashion.

Will I still be dressing like this in two years? Maybe not exactly, but I think I’ve permanently shifted toward prioritizing comfort and quality over trends. And honestly, if that makes me part of some grandfather fashion movement, I’m completely okay with that. Great-grandpa’s style is looking pretty prescient these days.