Picture this: December 15th, 6:30 PM, and I’m standing on the Red Line platform in my Theory blazer and what I thought was a foolproof sequined top from Banana Republic, watching my carefully planned corporate-girl-goes-to-Christmas-party look slowly disintegrate before I’ve even made it to Back Bay. The sequins are already snagging on everything—my coat zipper, the subway pole, probably the ambient air molecules at this point. My tights have developed a run that’s growing with each step like some kind of hosiery science experiment. The heels I optimistically thought I could wear for a twenty-minute commute are already staging a revolt against my feet.
I’m texting my colleague Maya about being late while simultaneously trying to keep my blazer from wrinkling against the subway seat, and I realize I look exactly like what I am: a finance professional who got dressed for a party in her Beacon Hill apartment and then had to actually navigate Boston public transportation to get there. It’s not a good look, literally or figuratively.
That night—which ended with me changing into emergency flats I bought at CVS and spending half the party trying to safety-pin my top back together in the bathroom—I made myself a promise. I work too hard and spend too much money on clothes to show up anywhere looking like I’ve been through a blender. There had to be a way to dress for these corporate holiday events that didn’t require me to choose between looking good and arriving in one piece.
So I spent the better part of last winter testing different approaches, treating every work event and client dinner like a laboratory for party-appropriate professional wear that could survive the T, Boston weather, and my own tendency to spill things on myself. The results have been… educational, let’s say.
First revelation: layering is everything, but it has to be strategic layering. Not the “throw on whatever’s warm” approach I’d been using, but what I started thinking of as defensive dressing. Base layer needs to be something that wicks moisture because heated subway cars in winter are basically saunas with worse ventilation. I discovered these seamless long-sleeve tops at Uniqlo that are thin enough to disappear under your actual outfit but keep you from freezing when you inevitably have to wait fifteen minutes for an Uber outside the venue.
The middle layer—the part people actually see—took more experimentation than I care to admit. Anything with loose sequins or beading is basically asking for disaster. I learned this the hard way when half the embellishments fell off a Zara top during one particularly crowded rush hour commute. Now I stick to pieces where the sparkle is woven into the fabric itself, not just glued on top.
My current go-to is this navy knit dress from COS with metallic threading running through it. Sounds boring, I know—when I first brought it home, my roommate asked if I was going to a funeral for a robot—but under party lighting it’s actually stunning. More importantly, I’ve worn it to four different events this season and it still looks perfect. At $120 it wasn’t cheap, but considering I’ve already gotten more wear out of it than most of my “special occasion” pieces, the math works.
For separates, I’ve found success with a black velvet blazer that I splurged on from Theory. The $285 price tag made me physically nauseous at the time, but two years later it’s still my most reliable party piece. The velvet is substantial enough to maintain its shape even when crushed against other commuters, and it automatically makes whatever you wear underneath look more expensive and intentional.
Bottom half strategy took some trial and error too. After one memorable incident involving a silk skirt and a rainstorm that left me looking like I’d been dipped in water halfway up my body, I’ve mostly switched to wide-leg trousers in darker colors. Not black—shows too much lint and general subway grime—but deep navy or burgundy. I found these high-waisted ones at Zara with subtle gold threading that gives just enough festive energy without screaming “I’m going to a party” to everyone on the Green Line.
The shoe situation remains the eternal struggle. I’ve tried the bring-party-shoes-separately approach, but that comes with its own risks. Last year I showed up to our year-end client event with two different black pumps because I’d been packing in my dark closet that morning. Another time my backup heels got soaked when my water bottle leaked in my bag, leaving me with wet leather nightmares.
My current solution is a pair of block-heeled ankle boots that can handle both the commute and the party. I invested in some from Stuart Weitzman that were painful at $350 but have been worth every penny. They’re comfortable enough for walking and standing on subway platforms, but sleek enough that I don’t feel underdressed when I arrive. The key was finding ones that had been treated for water resistance—Boston weather doesn’t care about your party plans.
If you’re committed to the full stiletto fantasy, those foldable ballet flats are lifesavers. Yes, they’re kind of ridiculous. Yes, you’ll look slightly insane changing shoes in the bathroom of whatever venue you’re going to. But they beat the alternative, which I learned during a particularly brutal client holiday party in 2019 when I ended up walking barefoot through Downtown Crossing because my feet had gone completely numb. Not my finest moment, professionally or personally.
Outerwear is where I used to make my biggest mistakes. I’d either freeze in something that looked good but provided zero warmth, or I’d bundle up in my everyday puffer coat and look like I was heading to a Bruins game instead of a corporate event. After much research and several expensive mistakes, I found this wool wrap coat from Reiss that hits the sweet spot. It was $425, which made me question all my life choices, but it’s roomy enough to go over party clothes without crushing them, structured enough to still look professional, and the wrap style means I can adjust the fit depending on what I’m wearing underneath.
For shorter commutes or when I’m feeling brave about the weather, I have a faux fur jacket from Warehouse that’s become my secret weapon. The emerald green color gets compliments from strangers, and the texture actually looks better slightly mussed, so being packed into the T works in its favor. Just don’t wear it in actual precipitation unless you enjoy the wet animal aesthetic.
I’ve learned to keep accessories minimal during travel. Statement earrings go in a small case in my bag until I reach my destination—after losing one of my favorite pairs somewhere between Park Street and my office building, I don’t take chances anymore. Same with delicate necklaces that seem magnetically attracted to getting tangled in coat zippers or scarf fringe.
The bag situation required its own strategy session. You need something large enough for touch-up supplies and weather contingencies, but not so massive you become that person taking up half a subway car. I settled on a structured leather tote that zips completely closed—crucial after several makeup explosion incidents—with a smaller clutch that fits inside for when I reach the event and want to look less like I’m carrying my entire life with me.
My ultimate test was last month’s holiday party for our biggest client. It was at the Four Seasons, dress code was “cocktail attire,” and naturally it was sleeting. Half the subway lines were delayed, it was freezing, and I had to transfer twice to get there. I wore the navy COS dress, the treated ankle boots, the wrap coat, and carried a carefully curated selection of emergency supplies—blotting papers, travel deodorant, lipstick, and Band-Aids for potential shoe casualties.
I arrived looking… well, not like I’d just stepped out of a magazine, but definitely not like I’d been recently involved in some kind of weather-related disaster. The highest compliment came from our managing director, Patricia, who pulled me aside during cocktails to ask how I’d managed to look “so polished” when she’d seen me emerging from the same subway entrance she’d used, looking significantly more battle-worn than I did.
“Strategic planning and a possibly unhealthy amount of thought put into practical party dressing,” I told her, right before demonstrating how my dress didn’t show wine stains by immediately spilling red wine on myself. Patricia now asks for my outfit advice before major client events, which I consider the ultimate professional endorsement.
The truth is, working in corporate finance means I go to a lot of these events—client dinners, holiday parties, industry networking things, company celebrations. They’re part of the job, and showing up looking put-together is part of maintaining credibility in this industry. But I also have to actually get to these events using normal transportation, in normal weather, while carrying normal bags full of the normal stuff I need to get through my day.
It took me way longer than I care to admit to figure out how to make that work without choosing between looking professional and arriving intact. But now that I’ve cracked the code, getting dressed for these events doesn’t fill me with the same dread it used to. I know what works, I know what doesn’t, and I know exactly which pieces in my closet can handle both the demands of looking appropriate for my industry and the reality of actually living in a city where you have to take public transportation to get anywhere.
Is it as glamorous as stepping out of a black car in something that cost more than my rent? Obviously not. But is it significantly more practical and infinitely less likely to end with me crying in a Logan Airport bathroom while trying to safety-pin my outfit back together before a work trip? Absolutely. And honestly, in the context of trying to build a successful career while also having a life outside the office, practical wins every time.
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.
