Last week I was supposed to be reviewing quarterly reports, but instead found myself staring out my office window at Downtown Crossing, watching people navigate the chaos of construction and tourists. You know how it is when you’re procrastinating—suddenly everything becomes fascinating. And honestly? What I saw completely changed how I think about East Coast style versus all those London street style blogs I’ve been obsessing over.
This woman walked past in what had to be a vintage Burberry trench (the kind your mom probably threw away in 1995 that’s worth a fortune now), but here’s the thing—she’d paired it with these perfectly beat-up New Balance 990s and was carrying what looked like a leather work tote that had seen some serious commuter action. The whole look was so effortlessly professional but practical, and I immediately felt like an idiot for spending $400 on those uncomfortable pointed-toe pumps I wore exactly twice before banishing them to the back of my closet.
I started paying attention after that, taking mental notes during my lunch walks and weekend errands. Three weeks of semi-stalking strangers later (don’t worry, I was subtle about it), I’ve realized we’ve been sleeping on Boston style. Everyone’s always going on about New York or LA or whatever European city is trending on Instagram, but there’s something happening here that’s actually more interesting than the overdone looks you see plastered all over fashion blogs.
In Back Bay on Saturday—I was hitting up the Newbury Street shops because my work wardrobe desperately needed something that wasn’t navy or gray—I kept noticing these incredibly chic women in what I can only describe as “expensive casual.” Like, $300 cashmere sweaters with perfectly faded jeans and sneakers that cost more than my monthly MetroCard budget. But the key was how lived-in everything looked. No one was trying to recreate a magazine spread; they were just wearing really good clothes that happened to work for their actual lives.
The jeans situation here is completely different from what I see in fashion magazines too. Everyone’s wearing these straight-leg styles that hit right at the ankle—not cropped, not dragging on the ground picking up street salt and God knows what else. They’re wearing them with everything from blazers for work to chunky sweaters for weekend errands. I found a pair at Everlane for $68 that’s become my uniform, and honestly, they make me feel more put-together than any of the designer pieces I convinced myself were “investment purchases” over the years.
The color palette here makes so much sense too. While fashion editors are pushing whatever bright shade is supposed to be revolutionary this season, Boston women have figured out that camel, cream, navy, and black just work. I watched this woman on the T yesterday—she was wearing a camel coat that probably cost more than my rent, white jeans (in March! The confidence!), and black ankle boots, and she looked like she’d stepped out of a very expensive catalog. But she was also reading a battered paperback and eating a breakfast sandwich, so clearly she understood that looking good doesn’t have to mean being precious about it.
The thing about Boston style is it’s never about the single statement piece—it’s about having everything in your closet work together seamlessly.
Accessories are where it gets really interesting though. I’ve been documenting—okay fine, photographing from a distance like a creep—the bags I see on my commute, and there’s this whole category of structured leather totes that seem to be the uniform around here. Not those tiny purses that fit nothing useful, but actual grown-up bags that can handle a laptop, lunch, and whatever random stuff you accumulate during a day of being a functioning adult. The best ones I’ve spotted are from Cuyana (expensive but worth it if you’re going to carry it every day for the next five years) and Madewell (more reasonable, still looks professional enough for client meetings).
And can we talk about shoes for a minute? Because I’ve been tracking this fascinating evolution away from the uncomfortable heels that fashion magazines insist we need for professional credibility. Everyone’s wearing these sleek ankle boots or clean white sneakers or—and this surprised me—really beautiful loafers. Not the frumpy ones your dad wears to his law firm, but these gorgeous leather ones that somehow manage to look both professional and cool. I broke down and bought a pair from Everlane after seeing them on approximately fifteen different women, and they’ve become my secret weapon for days when I need to look put-together but also walk more than two blocks without wanting to amputate my feet.
The sneaker thing is worth mentioning too. I used to think wearing sneakers with work clothes was giving up, but watching how women here style them has completely changed my perspective. They’re not wearing beat-up gym shoes with blazers—they’re wearing pristine white leather sneakers or those classic New Balance styles that somehow manage to look intentional rather than lazy. I’ve started wearing my white Veja sneakers with trousers and blazers, and honestly, I feel more confident knowing I can actually walk to meetings without suffering.
What’s fascinating is how different the approach is from what I see in corporate environments in other cities. When I was in New York for a conference last month, everyone looked like they were competing for best-dressed, but here there’s this understated thing happening that feels more sustainable. Like, you could wear the same basic uniform of good jeans, cashmere sweater, and structured coat five days a week and just swap out accessories, and you’d look perfectly appropriate for everything from client presentations to weekend brunch.
The layering game here is also next level, probably out of necessity because the weather makes no sense half the time. I watched this woman last week who had on a silk blouse, cashmere cardigan, and wool coat, but she’d chosen the colors so carefully—all these tonal grays and creams—that it looked elegant rather than bulky. I tried to recreate it with pieces from my closet and mostly succeeded, though my version involved significantly more polyester and cost about a tenth of what hers probably did.
I’ve been shopping my own closet differently since starting this little observation project. Turns out I had most of the pieces I needed; I just wasn’t putting them together in the right way. Those expensive trousers I bought for interviews but never wear because they felt too fancy? Perfect with a simple sweater and sneakers for weekend errands. That silk blouse I was saving for special occasions? Actually works great under a cardigan for normal Tuesday meetings.
The investment piece situation is real here though. I see the same high-quality basics over and over—those perfect white button-downs that actually fit properly, cashmere sweaters that don’t pill after three wears, coats that look expensive because they are expensive. But the smart thing I’ve noticed is how people wear these pieces constantly rather than saving them. That $200 sweater makes sense when you wear it twice a week for three months straight.
I’ve started a little spreadsheet (yes, I’m that person) tracking cost per wear on my clothes, and it’s been eye-opening. That $300 blazer from Theory that I wear to every important meeting? Down to about $12 per wear and dropping. Those $50 jeans from Target that I bought on sale and have worn maybe three times? Terrible investment, even though they seemed like a bargain.
Seeing how women here approach getting dressed has made me realize that good style isn’t about having the most current trends—it’s about understanding what works for your actual life and investing accordingly.
The confidence aspect is huge too. There’s something about seeing women who’ve figured out their formula and are sticking to it that’s really inspiring. They’re not checking fashion blogs every morning to see what they should be wearing; they’ve found their thing and they’re working it. I’ve been trying to channel that energy instead of constantly questioning whether my outfit is current enough or interesting enough or whatever arbitrary standard I was holding myself to before.
My shopping strategy has completely changed after this little experiment. Instead of buying trendy pieces that might work, I’m focusing on upgrading the basics I already know I love. Better versions of things I wear constantly rather than new categories entirely. It’s more expensive upfront but makes way more sense when I actually think about how I get dressed every morning.
This morning I wore my uniform—those Everlane jeans, a cashmere sweater I found on sale at Nordstrom Rack, ankle boots that are comfortable enough for my commute, and that structured tote that fits my laptop and lunch. Simple, professional, comfortable. Three colleagues complimented the outfit, which has literally never happened when I’ve tried to wear something trendy or fashion-forward to the office.
Maybe the secret isn’t following what fashion magazines say we should want, but paying attention to what actually works for the smart, stylish women around us. Sometimes the best style inspiration isn’t on Instagram—it’s walking past you on the street every day.
By day, Jasmine works in finance. By night, she writes about making corporate fashion actually interesting. Her Boston wardrobe proves office-appropriate doesn’t have to mean boring, and that investment dressing can be both powerful and personal.
